Title: 10 Best Hotels in Oakland, Chicago for 2025 | Expedia.ca

  

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# Hotels in Oakland, Chicago

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## Go beyond your typical stay in Oakland

Apart hotel

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-05&d1=2025-11-05&endDate=2025-11-07&d2=2025-11-07&lodging=APART_HOTEL)

Spa

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-05&d1=2025-11-05&endDate=2025-11-07&d2=2025-11-07&amenities=SPA_ON_SITE)

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-05&d1=2025-11-05&endDate=2025-11-07&d2=2025-11-07&amenities=PETS)

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-05&d1=2025-11-05&endDate=2025-11-07&d2=2025-11-07&travelerType=family_friendly)

Apart­ment

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-05&d1=2025-11-05&endDate=2025-11-07&d2=2025-11-07&lodging=APARTMENT)

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-05&d1=2025-11-05&endDate=2025-11-07&d2=2025-11-07&amenities=POOL)

Hot tub

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-05&d1=2025-11-05&endDate=2025-11-07&d2=2025-11-07&amenities=HOT_TUB)

Condo

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-05&d1=2025-11-05&endDate=2025-11-07&d2=2025-11-07&lodging=CONDO)

Waterpark

[](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America&regionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-05&d1=2025-11-05&endDate=2025-11-07&d2=2025-11-07&amenities=WATER_PARK)

## Check prices for these dates

Tonight

[Oct 22 - Oct 23](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-10-22&endDate=2025-10-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-10-23&endDate=2025-10-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Recommended

Price (low to high)

Distance

Star rating

## Oakland hotels and places to stay

![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/edcb7f57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Snack bar](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/7697ff8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite (Magnificent)](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/53a89031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Eurostars Magnificent Mile

River North, 8.1 km from Oakland

9.0/10

Wonderful

(3074)

"Excellent stay, close to everything and the staff was super nice "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kieata

CA $168

CA $198 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b1113923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/8e39b688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b131add8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 7.8 km from Oakland

8.8/10

Excellent

(2100)

"Great stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Melinda

CA $195

CA $229 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information)

![Cocktail bar](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/50be090a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/ada94c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/56c2d84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aloft Chicago Mag Mile

Streeterville, 7.9 km from Oakland

8.6/10

Excellent

(2862)

"Had a great stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Josh

CA $172

CA $202 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information)

![Reception](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/511c43ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Single Beds](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/6d4883c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e50ef89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River Hotel

The Loop, 7.4 km from Oakland

8.8/10

Excellent

(4734)

"Staff friendly and helpful..and accommodations just right..great location! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Adrienne

CA $143

CA $168 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/a9c979ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/2866aa1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 7.5 km from Oakland

9.4/10

Exceptional

(2210)

"Rooms were clean with a great view of the lake and the city "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nathan

CA $223

CA $310 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information)

![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/cb4330d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/2aaf07f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/c14e1876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Freehand Chicago

River North, 7.9 km from Oakland

8.0/10

Very good

(2508)

"Very accessible location and amazing staff. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Fatima

CA $108

CA $152 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/bb272e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily buffet breakfast (USD 20.00 per person)](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/8967eebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/1792d463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### citizenM Chicago Downtown

Theatre District, 7.3 km from Oakland

9.4/10

Exceptional

(3982)

"Great place to stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

sherry

CA $184

CA $215 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information)

![Banquet hall](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e43f096f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Suite, 1 King Bed, Lake View, Lakeside](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e932b9a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Congress Plaza Hotel

The Loop, 6 km from Oakland

8.0/10

Very good

(9541)

"Area is great and walkable distance to touring areas. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alejandro

CA $160

CA $188 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/59baefbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/18c5ca41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/5e299c2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Chicago Downtown/Magnificent Mile

River North, 7.8 km from Oakland

8.4/10

Very good

(4115)

"This hotel had a great location to shopping and several enjoyable restaurants."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

laura

CA $167

CA $196 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information)

![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/0030a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/07c9ead9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/172457c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Chicago/Magnificent Mile Suites

Streeterville, 8.6 km from Oakland

9.0/10

Wonderful

(3128)

"Our stay was great"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bruce E

CA $163

CA $192 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed | Living area](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b812d0f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b5bf3aa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/f2c5642d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Chicago

The Loop, 5.7 km from Oakland

8.4/10

Very good

(2260)

"We loved this hotel it was beautiful and convenient . "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Daniel

CA $258

CA $344 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information)

![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/f7f78ace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/b6152ff3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/f9eed5f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/520a670b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western River North Hotel

River North, 8 km from Oakland

7.8/10

Good

(1001)

"Great stay"

![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg)

Bart

CA $142

CA $166 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Chicago-Hotels-Best-Western-River-North-Hotel.h17227.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/cbeee5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/9ab0dcf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/2b6118c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/0c9aebe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FOUND Hotel Chicago River North

River North, 8.1 km from Oakland

8.2/10

Very good

(280)

"Perfect location! Tons of restaurants and shopping nearby! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

MaryJane

CA $107

CA $125 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Chicago-Hotels-FOUND-Hotel-Chicago.h113779814.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Snack bar](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/c0ded825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/f5c52beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/2f70f55e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Riu Plaza Chicago

Streeterville, 7.9 km from Oakland

9.4/10

Exceptional

(2630)

"Great place to stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Larry William

CA $181

CA $252 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)

![American cuisine](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily buffet breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/c46ad167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![American cuisine](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/fb80c7da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/871940a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Crowne Plaza Chicago West Loop by IHG

7.3 km from Oakland

9.0/10

Wonderful

(1616)

"Great Hotel"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cesar

CA $165

CA $194 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information)

![Bar (on property)](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/6b27f192.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, laptop workspace, free cribs/infant beds](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/64c4029a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/ddbd86a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/5496cb17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### voco Chicago Downtown - Riverwalk by IHG

River North, 7.7 km from Oakland

8.8/10

Excellent

(3243)

"Great stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

shanae

CA $247

CA $290 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/3000000/2510000/2506500/2506471/b573f792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/3000000/2510000/2506500/2506471/0aef82d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2510000/2506500/2506471/d5770f58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2510000/2506500/2506471/b4d2cc05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 7 km from Oakland

8.6/10

Excellent

(2571)

"Very nice for price and location"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Deborah

CA $175

CA $231 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chicago-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Chicago-Downtown.h2506471.Hotel-Information)

![Rooftop terrace](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/af0ef9e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/w3576h2561x0y0-5f9110d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/0ec157ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Rooftop terrace](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/d36b65bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Centric The Loop Chicago

Theatre District, 6.7 km from Oakland

9.0/10

Wonderful

(2201)

"It was an amazing stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kristy S

CA $208

CA $245 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-The-Loop-Chicago.h9069667.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/04b62050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Serves breakfast, lunch, and dinner](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/b0f5bd1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/c5cac7c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Silversmith Hotel Chicago Downtown

Theatre District, 6.7 km from Oakland

9.4/10

Exceptional

(2015)

"Great place to stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cheryl

CA $160

CA $231 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information)

![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/01c93cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/8318473d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Palmer House a Hilton Hotel

Theatre District, 6.7 km from Oakland

8.4/10

Very good

(2030)

"Great place to stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ron

CA $247

CA $325 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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## Hotels in Oakland with a pool

![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/e47956bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/943262bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/6d9bcb03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Wade

Streeterville, 7.9 km from Oakland

-   Pool
    

8.4/10

Very good

(1378)

CA $189

CA $222 total

includes taxes & fees

Nov 18 - Nov 19

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-18&endDate=2025-11-19&selected=1346&PinnedHotelID=1346&HadPinnedHotel=true&regionId=6132392&adults=2&amenities=POOL&openPlayBack=true)

![Bar (on property)](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/6b27f192.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, laptop workspace, free cribs/infant beds](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/64c4029a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/ddbd86a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/5496cb17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### voco Chicago Downtown - Riverwalk by IHG

River North, 7.7 km from Oakland

-   Pool
    

8.8/10

Excellent

(3243)

CA $247

CA $290 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-09&endDate=2025-11-10&selected=76459163&PinnedHotelID=76459163&HadPinnedHotel=true&regionId=6132392&adults=2&amenities=POOL&openPlayBack=true)

![Pool](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/d5b5d773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/6dc8c836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/3b2677cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/0f103d66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

-   Pool
    

8.8/10

Excellent

(1706)

CA $148

CA $173 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-10&endDate=2025-11-11&selected=33682469&PinnedHotelID=33682469&HadPinnedHotel=true&regionId=6132392&adults=2&amenities=POOL&openPlayBack=true)

![Room, 1 King Bed, Corner](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2249x3y0-2724cf53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/461957e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2584x3y3-d51aee41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2496x3y3-f9e98aea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Centric Chicago Magnificent Mile

Streeterville, 8 km from Oakland

-   Pool
    

9.0/10

Wonderful

(1028)

CA $222

CA $301 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-09&endDate=2025-11-10&selected=151139&PinnedHotelID=151139&HadPinnedHotel=true&regionId=6132392&adults=2&amenities=POOL&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/10000000/9060000/9059600/9059537/ddbc274d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/10000000/9060000/9059600/9059537/baa44a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/10000000/9060000/9059600/9059537/f6a223b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/10000000/9060000/9059600/9059537/af468b77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Loews Chicago Hotel

Streeterville, 7.5 km from Oakland

-   Pool
    

9.4/10

Exceptional

(1575)

CA $293

CA $388 total

includes taxes & fees

Oct 29 - Oct 30

[](https://www.expedia.ca/Hotel-Search?startDate=2025-10-29&endDate=2025-10-30&selected=9059537&PinnedHotelID=9059537&HadPinnedHotel=true&regionId=6132392&adults=2&amenities=POOL&openPlayBack=true)

![Breakfast and lunch served](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/529d8be8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast and lunch served](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/913433f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/7705f099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/120d903c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Courtyard by Marriott Chicago Magnificent Mile

Streeterville, 7.9 km from Oakland

-   Pool
    

8.8/10

Excellent

(1550)

CA $217

CA $255 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-09&endDate=2025-11-10&selected=982517&PinnedHotelID=982517&HadPinnedHotel=true&regionId=6132392&adults=2&amenities=POOL&openPlayBack=true)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/4c0ebbe4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/311c65a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake view](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/247d9e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV, Netflix, pay movies, streaming services](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/edeb1954.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sheraton Grand Chicago Riverwalk

Streeterville, 7.4 km from Oakland

-   Pool
    

8.4/10

Very good

(1540)

CA $279

CA $370 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-09&endDate=2025-11-10&selected=12167&PinnedHotelID=12167&HadPinnedHotel=true&regionId=6132392&adults=2&amenities=POOL&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/da498d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ballroom](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/db08811d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/be69fa71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/71356b17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 7.6 km from Oakland

-   Pool
    

8.2/10

Very good

(2741)

CA $225

CA $306 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-09&endDate=2025-11-10&selected=570329&PinnedHotelID=570329&HadPinnedHotel=true&regionId=6132392&adults=2&amenities=POOL&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed | Living area](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b812d0f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b5bf3aa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/f2c5642d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Chicago

The Loop, 5.7 km from Oakland

-   Pool
    

8.4/10

Very good

(2260)

CA $258

CA $344 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Hotel-Search?startDate=2025-10-30&endDate=2025-10-31&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true&regionId=6132392&adults=2&amenities=POOL&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/7012a512.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/a07d9bd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor wedding](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/481e5f5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Chicago Dwtn - The Mart by IHG

River North, 7.7 km from Oakland

-   Pool
    

8.8/10

Excellent

(1958)

CA $233

CA $274 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-09&endDate=2025-11-10&selected=5467&PinnedHotelID=5467&HadPinnedHotel=true&regionId=6132392&adults=2&amenities=POOL&openPlayBack=true)

[See more properties](https://www.expedia.ca/Hotel-Search?startDate=2025-11-05&endDate=2025-11-06&regionId=6132392&adults=2&sort=RECOMMENDED&amenities=POOL&openPlayBack=true)

## Top guest rated hotels in Oakland

![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/cb4330d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/2aaf07f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/c14e1876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Freehand Chicago

River North, 7.9 km from Oakland

8.0/10

Very good

(2508)

CA $108

CA $152 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-10&endDate=2025-11-11&selected=9418281&PinnedHotelID=9418281&HadPinnedHotel=true&regionId=6132392&adults=2&guestRating=35&openPlayBack=true)

![Front of property](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Snack bar](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/c0ded825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/f5c52beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/2f70f55e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Riu Plaza Chicago

Streeterville, 7.9 km from Oakland

9.4/10

Exceptional

(2630)

CA $181

CA $252 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-09&endDate=2025-11-10&selected=102622712&PinnedHotelID=102622712&HadPinnedHotel=true&regionId=6132392&adults=2&guestRating=35&openPlayBack=true)

![Reception](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/511c43ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Single Beds](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/6d4883c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e50ef89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River Hotel

The Loop, 7.4 km from Oakland

8.8/10

Excellent

(4734)

CA $143

CA $168 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-11&endDate=2025-11-12&selected=2675313&PinnedHotelID=2675313&HadPinnedHotel=true&regionId=6132392&adults=2&guestRating=35&openPlayBack=true)

![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/8750140b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/c8177aa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/fd235ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Whitehall Hotel, BW Premier Collection

Streeterville, 8.6 km from Oakland

8.2/10

Very good

(3627)

CA $125

CA $147 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&selected=17903&PinnedHotelID=17903&HadPinnedHotel=true&regionId=6132392&adults=2&guestRating=35&openPlayBack=true)

![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/0030a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/07c9ead9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/172457c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Chicago/Magnificent Mile Suites

Streeterville, 8.6 km from Oakland

9.0/10

Wonderful

(3128)

CA $163

CA $192 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true&regionId=6132392&adults=2&guestRating=35&openPlayBack=true)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/023ff9a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/43039f7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/ccacdd84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Warwick Allerton - Chicago

Magnificent Mile, 8.1 km from Oakland

8.4/10

Very good

(2912)

CA $140

CA $206 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-12&endDate=2025-11-13&selected=25452&PinnedHotelID=25452&HadPinnedHotel=true&regionId=6132392&adults=2&guestRating=35&openPlayBack=true)

![Cocktail bar](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/50be090a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/ada94c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/56c2d84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aloft Chicago Mag Mile

Streeterville, 7.9 km from Oakland

8.6/10

Excellent

(2862)

CA $172

CA $202 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-09&endDate=2025-11-10&selected=26998765&PinnedHotelID=26998765&HadPinnedHotel=true&regionId=6132392&adults=2&guestRating=35&openPlayBack=true)

![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/a243f0c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/79f898c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/b9d3aa50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/c2bb1544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Grant Park Hotel

The Loop, 5.4 km from Oakland

8.2/10

Very good

(2600)

CA $118

CA $139 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-10&endDate=2025-11-11&selected=23023&PinnedHotelID=23023&HadPinnedHotel=true&regionId=6132392&adults=2&guestRating=35&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/59baefbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/18c5ca41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/5e299c2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Chicago Downtown/Magnificent Mile

River North, 7.8 km from Oakland

8.4/10

Very good

(4115)

CA $167

CA $196 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-11&endDate=2025-11-12&selected=424187&PinnedHotelID=424187&HadPinnedHotel=true&regionId=6132392&adults=2&guestRating=35&openPlayBack=true)

![Cocktail bar](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/5ea33759.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cocktail bar](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/bab7a943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, hypo-allergenic bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/880fa2cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/2d37be79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Claridge House

Gold Coast, 9.3 km from Oakland

9.0/10

Wonderful

(1400)

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-05&endDate=2025-11-06&selected=22684&PinnedHotelID=22684&HadPinnedHotel=true&regionId=6132392&adults=2&guestRating=35&openPlayBack=true)

[See more properties](https://www.expedia.ca/Hotel-Search?startDate=2025-11-05&endDate=2025-11-06&regionId=6132392&adults=2&sort=RECOMMENDED&guestRating=35&openPlayBack=true)

## Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most.

-   Downtown Chicago
-   Magnificent Mile
-   The Loop
-   River North
-   Lincoln Park

![Downtown Chicago showing a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332072-Downtown-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191755-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Downtown Chicago which includes a high-rise building and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332087-Downtown-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Downtown Chicago featuring signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332073-Downtown-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Downtown Chicago featuring a city and signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332084-Downtown-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=6350699)

![Downtown Chicago map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:uxq%7EFvjavOurAq%40mA%7DgDuTtO%7BFzJuOr%40mk%40z_%40MifBum%40%7EAGmaAx%7EAopCna%40uM%7EoC%7C%7DAx%40%7CkCnk%40yAy%40n%7B%40gt%40dE%7Bg%40pFo%40%60%7EB&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=XpzTv33-iXOpq3icViGLtz3e_jE=)

### Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=6350699)

![Magnificent Mile - River North](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24577-Magnificent-Mile.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543374-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Magnificent Mile - River North showing signage and heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191832-Magnificent-Mile.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Magnificent Mile - River North which includes street scenes as well as a large group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191836-Magnificent-Mile.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Magnificent Mile - River North showing a hotel, a city and modern architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24572-Magnificent-Mile.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=800025)

![Magnificent Mile map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:gnt%7EF%60dyuOugAK%3FcChgALJ%60C&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=eJaOW3wrdH9kguwKvLeM9_7UbMs=)

### Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=800025)

![The Loop - Downtown featuring a river or creek](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192013-The-Loop-Downtown.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543387-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543370-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![The Loop - Downtown featuring a river or creek and a ferry](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191752-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192010-The-Loop-Downtown.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=800024)

![The Loop map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:syr%7EFxx%7BuOqa%40mAeEqK_%40sp%40kG%7BKvAwg%40Xok%40%7C_%40x%40xF%7EPtlAi%40dCh%40DzOxDxCDnbBkNr%40e%5E%7EEkKzGiVfC&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=XwfHKgKFqor-NvwNZdw8nZOnNbI=)

### The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=800024)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543369-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543384-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Shops at North Bridge which includes central business district, a city and street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191962-Shops-At-North-Bridge.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191756-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Shops at North Bridge showing a city, central business district and street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191961-Shops-At-North-Bridge.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=6350695)

![River North map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:%7B%7Cu%7EFl_%7DuOWcpA%7CECQ%7Db%40xi%40w%40nGbNJ%7Ep%40xCbHxAdBcB%7ECuAhA%7DKdCyGvFiGdDsD%7CDeCzEwBfBoN%5E&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=pVk_WdkeHd9iD-9kitVtoqcFN2A=)

### River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=6350695)

![Chicago which includes modern architecture and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54398-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24578-Chicago-History-Museum.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Lincoln Park Zoo showing autumn colours and signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26661-Lincoln-Park-Zoo.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24579-Chicago-History-Museum.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Chicago History Museum featuring interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24583-Chicago-History-Museum.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=6059328)

![Lincoln Park map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:u%7E%7C%7EFhscvO%40%7DMjAWEyE_JFsDaCAl%40qDD%3F%7DBjU_%40AkAiAQ%40aWbAKAyFqALQeJzAIKaNiAJOgUTi%40%7E%40KEgF_BD%3FuMbBMc%40_NiAAI%7DImAIKmB%7CAQMeVxAKQ%7BOwGaCnCQHeCtBKFgC%7DAUSaGbBIx%40i%60Axp%40mMbD%7EGpa%40%7DJpR%7DM%60NgVzGrLV%60n%40mJ%7EEh%40%60AfIKClIuCNp%40xRrBWl%40b%7EAoEJoElF%7CArEjIiGKpNoVzJqItQvCfKsArA%7DL%60FuXhVm%40%60NaKhR%7BK%7CAcFbKiAzFsK_MqLbN%7DAJ&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=KktfaLNeQ_9ZFVphttKdls3N5TA=)

### Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=6059328)

## Top Oakland Hotel Reviews

![Hotel Riu Plaza Chicago](//images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg)

### Hotel Riu Plaza Chicago

10/10 Excellent

"fresh breakfast attentive and pleasant staff"

[](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)

![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Parking was terrible and expensive. Recommend valet parking. Staff, very hard to talk to and i arrived at 3:30 scheduled to check in at 4 pm. Room wasn't available until 4;30. Staff wasn't to concerned."

[](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information)

![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Nice location, rooms were nice size beds were comfortable water pressure was great "

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![Sable at Navy Pier Chicago, Curio Collection by Hilton](//images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Excellent

"Location, location, location"

[](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information)

![The Royal Sonesta Chicago Downtown](//images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg)

### The Royal Sonesta Chicago Downtown

10/10 Excellent

"The room was great, view gorgeous and all the hotel staff were welcoming and helpful! Location of the hotel is perfect to walk or take the metro. The restaurant had limited choices for breakfast but was nice enough and convenient."

[](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information)

![Hilton Garden Inn Chicago Downtown/Magnificent Mile](//images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg)

### Hilton Garden Inn Chicago Downtown/Magnificent Mile

10/10 Excellent

"It was affordable "

[](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information)

![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg)

### The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"It was a beautiful property in a spectacular location. Close to transit, and walkable to everything in the loop. Would definitely stay again. "

[](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information)

![Crowne Plaza Chicago West Loop by IHG](//images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3_y.jpg)

### Crowne Plaza Chicago West Loop by IHG

10/10 Excellent

"Excellent staff and overall experience. "

[](https://expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information)

![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg)

### Freehand Chicago

10/10 Excellent

"Great Vibe!"

[](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information)

## Frequently asked questions

### What are the best hotels in Oakland that travellers recommend?

> [Sophy Hyde Park](https://www.expedia.ca/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information) is a standout hotel located in the vibrant city of Chicago, boasting an exceptional score of 9.6. Guests appreciate its blend of modern luxury and historical charm, with high-end amenities such as premium bedding, customized bathrobes, and a stunning terrace great for relaxation. The hotel's prime location in the Historical District allows easy access to local attractions, making it an ideal choice for couples seeking a romantic getaway or travellers looking to explore the city's rich culture.
> 
>   
> 
> For families, the [Hyatt Place Chicago-South/University Medical Center](https://www.expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) shines with a rating of 8.8. Its spacious rooms feature sofa beds and cribs, ensuring comfort for all ages. The hotel offers a complimentary buffet breakfast, making mornings straightforward. Kids will love the indoor pool, while parents can enjoy the 24-hour fitness facilities. The family-friendly atmosphere is enhanced by the option for kids' meals, allowing everyone to dine happily together.

### What hotels in Oakland offer free breakfast?

> [Hyatt Place Chicago-South/University Medical Center](https://www.expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) is a fantastic option for families visiting Chicago. Rated 8.8 by guests, this hotel offers a complimentary buffet breakfast, ensuring that everyone starts the day off right. With an indoor pool, kids can splash around while parents unwind, making it a great spot for family fun.

### What are the best budget hotels in Oakland?

> [Hyatt Place Chicago-South/University Medical Center](https://www.expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) is an excellent budget-friendly option for families visiting Chicago. This hotel boasts a spacious indoor pool, which is great for kids to splash around while parents relax nearby. Guests appreciate the complimentary breakfast, featuring a delightful buffet that caters to various tastes, ensuring the whole family starts their day right.

### What are the most romantic hotels in Oakland for couples?

> For couples seeking a romantic getaway in Oakland, [Sophy Hyde Park](https://www.expedia.ca/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information) is an exceptional choice, boasting a stellar rating of 9.6. This hotel is situated in a charming historical district, enveloping guests in a special environment that melds history with modern comforts.

### Can I cancel my hotel reservation on Expedia?

> Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Oakland hotel for you.

### How can I save on a Oakland hotel booking with Expedia?

> Before booking your Oakland hotel, remember to join Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. You could also enjoy savings by bundling together your hotel and flights on Expedia.

### How much is the nightly rate at a Oakland hotel?

> Hotel prices in Oakland often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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-   [Cottages in Chicago](https://expedia.ca/Chicago-Cottages.d178248-aaCottages.Travel-Guide-Accommodation)
-   [Guest Houses in Chicago](https://expedia.ca/Chicago-Guest-Houses.d178248-aaGuestHouses.Travel-Guide-Accommodation)
-   [Villas in Chicago](https://expedia.ca/Chicago-Villas.d178248-aaVillas.Travel-Guide-Accommodation)
-   [Hostels in Chicago](https://expedia.ca/Chicago-Hostels.d178248-aaHostels.Travel-Guide-Accommodation)
-   [Resorts in Chicago](https://expedia.ca/Chicago-Resort-Hotels.d178248-aaResortHotels.Travel-Guide-Accommodation)
-   [Cabin Rentals in Chicago](https://expedia.ca/Chicago-Cabins.d178248-aaCabins.Travel-Guide-Accommodation)
-   [Farmstay in Chicago](https://expedia.ca/Chicago-Agritourism.d178248-aaAgritourism.Travel-Guide-Accommodation)
-   [RV Parks in Chicago](https://expedia.ca/Chicago-RV-Parks.d178248-aaRVParks.Travel-Guide-Accommodation)
-   [Houseboats in Chicago](https://expedia.ca/Chicago-Houseboats.d178248-aaHouseboats.Travel-Guide-Accommodation)
-   [Inns in Chicago](https://expedia.ca/Chicago-Inns.d178248-aaInns.Travel-Guide-Accommodation)
-   [Residences in Chicago](https://expedia.ca/Chicago-Residences.d178248-aaResidences.Travel-Guide-Accommodation)

### Hotels Close to Nearby Airports

-   [Hotels near O'Hare Intl. Airport](https://expedia.ca/OHare-Intl-Airport-Hotels.0-aORD-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Midway Intl. Airport](https://expedia.ca/Midway-Intl-Airport-Hotels.0-aMDW-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Chicago Executive Airport](https://expedia.ca/Chicago-Executive-Airport-Hotels.0-aPWK-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Dupage Airport](https://expedia.ca/Dupage-Airport-Hotels.0-aDPA-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Greater Rockford Airport](https://expedia.ca/Greater-Rockford-Airport-Hotels.0-aRFD-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Gary - Chicago Intl. Airport](https://expedia.ca/Gary-Chicago-Intl-Airport-Hotels.0-aGYY-0.Travel-Guide-Filter-Hotels)

### Oakland Hotels by Star Rating

-   [2 Star Hotels in Oakland](https://expedia.ca/2Star-Oakland-Chicago-Hotels.s20-n6132392-0.Travel-Guide-Filter-Hotels)
-   [3 Star Hotels in Oakland](https://expedia.ca/3Star-Oakland-Chicago-Hotels.s30-n6132392-0.Travel-Guide-Filter-Hotels)
-   [4 Star Hotels in Oakland](https://expedia.ca/4Star-Oakland-Chicago-Hotels.s40-n6132392-0.Travel-Guide-Filter-Hotels)
-   [5 Star Hotels in Oakland](https://expedia.ca/5Star-Oakland-Chicago-Hotels.s50-n6132392-0.Travel-Guide-Filter-Hotels)

### Oakland Hotels by Brand

-   [Best Western Hotels](https://expedia.ca/Oakland-Chicago-Hotels-Best-Western.0-n6132392-0--bBestWestern.Travel-Guide-Filter-Hotels)
-   [Club Quarters Hotels](https://expedia.ca/Oakland-Chicago-Hotels-Club-Quarters.0-n6132392-0--bClubQuarters.Travel-Guide-Filter-Hotels)
-   [Fairmont Hotels](https://expedia.ca/Oakland-Chicago-Hotels-Fairmont.0-n6132392-0--bFairmont.Travel-Guide-Filter-Hotels)
-   [Hilton Hotels Hotels](https://expedia.ca/Oakland-Chicago-Hotels-Hilton-Hotels.0-n6132392-0--bHiltonHotels.Travel-Guide-Filter-Hotels)
-   [Independent Hotels](https://expedia.ca/Oakland-Chicago-Hotels-Independent.0-n6132392-0--bIndependent.Travel-Guide-Filter-Hotels)
-   [La Quinta Inn & Suites Hotels](https://expedia.ca/Oakland-Chicago-Hotels-La-Quinta-Inn-Suites.0-n6132392-0--bLaQuintaInnSuites.Travel-Guide-Filter-Hotels)
-   [Loews Hotels](https://expedia.ca/Oakland-Chicago-Hotels-Loews.0-n6132392-0--bLoews.Travel-Guide-Filter-Hotels)
-   [Marriott Hotels & Resorts Hotels](https://expedia.ca/Oakland-Chicago-Hotels-Marriott-Hotels-Resorts.0-n6132392-0--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels)
-   [Motel 6 Hotels](https://expedia.ca/Oakland-Chicago-Hotels-Motel-6.0-n6132392-0--bMotel6.Travel-Guide-Filter-Hotels)
-   [Red Roof Inn Hotels](https://expedia.ca/Oakland-Chicago-Hotels-Red-Roof-Inn.0-n6132392-0--bRedRoofInn.Travel-Guide-Filter-Hotels)
-   [Sonesta Hotel Hotels](https://expedia.ca/Oakland-Chicago-Hotels-Sonesta-Hotel.0-n6132392-0--bSonestaHotel.Travel-Guide-Filter-Hotels)

### Explore more hotels

-   [Hotel Felix River North/Magnificent Mile](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information)
-   [Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical](https://expedia.ca/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Downtown.h25929.Hotel-Information)
-   [Crowne Plaza Chicago West Loop by IHG](https://expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information)
-   [Aloft Chicago Mag Mile](https://expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information)
-   [Hotel Riu Plaza Chicago](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)
-   [Pendry Chicago](https://expedia.ca/Chicago-Hotels-Pendry-Chicago.h982552.Hotel-Information)
-   [The Royal Sonesta Chicago Downtown](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information)
-   [InterContinental Chicago Magnificent Mile by IHG](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information)
-   [Hilton Chicago](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information)
-   [Palmer House a Hilton Hotel](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information)
-   [LondonHouse Chicago, Curio Collection by Hilton](https://expedia.ca/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information)
-   [Hyatt Regency Chicago](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information)

[See a list of all hotels in Chicago](https://expedia.ca/All-Chicago-Hotels.d178248.Travel-Guide-City-All-Hotels)

### More ways to book

-   [Book Hotels in Oakland on Expedia.com](https://www.expedia.com/Oakland-Chicago-Hotels.0-n6132392-0.Travel-Guide-Filter-Hotels)

### Expedia's Latest Trends

Hotels

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Flights

-   [Flights from Kelowna to Edmonton](https://expedia.ca/lp/flights/ylw/yeg/kelowna-to-edmonton)
-   [Flights from Toronto to Chicago](https://expedia.ca/lp/flights/yyz/ord/toronto-to-chicago)
-   [Flights from Toronto to New York](https://expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)
-   [Air Canada](https://expedia.ca/Air-Canada-Flights.cAC.Travel-Guide-Airlines)
-   [Cheap Flights to Bali](https://expedia.ca/Destinations-In-Bali.d602651.Flight-Destinations)
-   [Flights from Toronto to Québec](https://expedia.ca/lp/flights/yyz/yqb/toronto-to-quebec)
-   [Cheap Flights to Texas](https://expedia.ca/Destinations-In-Texas.d245.Flight-Destinations)

Cars

-   [Car rentals in Canada](https://expedia.ca/Destinations-In-Canada.d31.Car-Rental-Destinations)

Packages

-   [Downtown Chicago Vacations](https://expedia.ca/Downtown-Chicago.d6350699.Destination-Travel-Guides)

General

-   [Visit Magnificent Mile](https://expedia.ca/Chicago-Magnificent-Mile.dx800025)
-   [Visit The Loop](https://expedia.ca/Chicago-The-Loop.dx800024)
-   [Visit Downtown Chicago](https://expedia.ca/Chicago-Downtown-Chicago.dx6350699)