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

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=2025-11-22&d1=2025-11-22&endDate=2025-11-24&d2=2025-11-24&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=2025-11-22&d1=2025-11-22&endDate=2025-11-24&d2=2025-11-24&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=2025-11-22&d1=2025-11-22&endDate=2025-11-24&d2=2025-11-24&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=2025-11-22&d1=2025-11-22&endDate=2025-11-24&d2=2025-11-24&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=2025-11-22&d1=2025-11-22&endDate=2025-11-24&d2=2025-11-24&lodging=CONDO)

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=2025-11-22&d1=2025-11-22&endDate=2025-11-24&d2=2025-11-24&amenities=PETS)

Cottage

[](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=2025-11-22&d1=2025-11-22&endDate=2025-11-24&d2=2025-11-24&lodging=COTTAGE)

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=2025-11-22&d1=2025-11-22&endDate=2025-11-24&d2=2025-11-24&amenities=WATER_PARK)

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=2025-11-22&d1=2025-11-22&endDate=2025-11-24&d2=2025-11-24&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=2025-11-22&d1=2025-11-22&endDate=2025-11-24&d2=2025-11-24&amenities=SPA_ON_SITE)

## Check prices for these dates

Tonight

[Nov 8 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-11-08&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 9 - Nov 10](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-11-09&endDate=2025-11-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-11-21&endDate=2025-11-23&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)

![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/e69bed89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/06b28362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception hall](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Eurostars Magnificent Mile

River North, 8.1 km from Oakland

8.8/10

Excellent

(3084)

"Awesome location and excellent service, the staff was great!"

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

Salvador

CA $136

CA $160 total

includes taxes & fees

Dec 7 - Dec 8

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

![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)

![Business centre](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/511c43ea.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

(4778)

"Beautiful hotel. Had a nice stay"

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

Esther

CA $112

CA $131 total

includes taxes & fees

Dec 7 - Dec 8

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

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

![Reception](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/d7ae47e3.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)

### DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 7.8 km from Oakland

8.8/10

Excellent

(2129)

"Very nice hotel "

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

Patrick

CA $134

CA $157 total

includes taxes & fees

Nov 23 - Nov 24

[](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)

![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.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

(2879)

"Clean room and loved the atmosphere"

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

Madison

CA $138

CA $162 total

includes taxes & fees

Nov 26 - Nov 27

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

![2 bars/lounges](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/55a8ba7b.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/58000000/57660000/57651200/57651125/5d460cc6.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

(2215)

"Room was spotless…staff was great!"

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

Tamika

CA $145

CA $218 total

includes taxes & fees

Nov 25 - Nov 26

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

![Room, 1 King Bed, City View | View from room](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/c06f4b61.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)

![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)

### citizenM Chicago Downtown

Theatre District, 7.3 km from Oakland

9.2/10

Wonderful

(4064)

"Clean rooms, friendly staff, great breakfast, amazing location. "

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

Gokce

CA $160

CA $188 total

includes taxes & fees

Nov 10 - Nov 11

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

![Reception](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/5132819a.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 detail](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/cb4330d2.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

(2574)

"Great place. "

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

John

CA $94

CA $136 total

includes taxes & fees

Dec 8 - Dec 9

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

![Reception](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/b9be2277.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)

### Hilton Garden Inn Chicago Downtown/Magnificent Mile

River North, 7.8 km from Oakland

8.4/10

Very good

(4135)

"Clean rooms and friendly staff"

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

Jeffrey

CA $131

CA $154 total

includes taxes & fees

Dec 7 - Dec 8

[](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)

![View from room](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/d24507d4.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)

![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/07c9ead9.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

(3240)

"Overall it was a great place to stay."

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

Edward

CA $143

CA $168 total

includes taxes & fees

Dec 7 - Dec 8

[](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)

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

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/bbeef356.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

(2284)

"Great Hotel"

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

Luz

CA $159

CA $228 total

includes taxes & fees

Nov 24 - Nov 25

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

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

![Junior Suite, City View | Living area](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/cc919354.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)

### Congress Plaza Hotel

The Loop, 6 km from Oakland

8.0/10

Very good

(9517)

"Great stay comfortable bed and great location!"

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

Kimberly Noel

CA $111

CA $131 total

includes taxes & fees

Nov 10 - Nov 11

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

![Exterior](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/2f70f55e.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)

### Hotel Riu Plaza Chicago

Streeterville, 7.9 km from Oakland

9.4/10

Exceptional

(2724)

"Nice hotel, very clean and the buffet breakfast was excellent "

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

Veronica Anne

CA $146

CA $211 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.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/114000000/113780000/113779900/113779814/2b6118c9.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/114000000/113780000/113779900/113779814/68145d79.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

(306)

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

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

MaryJane

CA $95

CA $111 total

includes taxes & fees

Dec 7 - Dec 8

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

![Lobby](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/5b3c70b2.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)

![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

(1660)

"Great hotel and amenities "

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

Adrienne

CA $127

CA $149 total

includes taxes & fees

Nov 23 - Nov 24

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

![Seasonal outdoor pool, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/210000/201300/201274/bcc149aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/1000000/210000/201300/201274/4e117aab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/210000/201300/201274/d0389723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/1000000/210000/201300/201274/fef288c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn & Suites Chicago - Downtown by IHG

West Loop, 6.4 km from Oakland

8.4/10

Very good

(1004)

"Really great location and warm and friendly staff"

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

David

CA $166

CA $211 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Suites-Chicago-Downtown.h201274.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)

![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/5496cb17.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/dd081548.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

(3324)

"Great stay!"

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

Shanell

CA $146

CA $171 total

includes taxes & fees

Nov 24 - Nov 25

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

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/05f95ad0.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)

![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

(2041)

"Great spot"

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

Kirsten

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

![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)

![Lobby](https://images.trvl-media.com/lodging/3000000/2510000/2506500/2506471/891da469.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

(2596)

"Lovely staff and great rooms at great price and location! "

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

Diana

CA $138

CA $186 total

includes taxes & fees

Nov 23 - Nov 24

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

![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/aaad0ec5.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)

![Reception](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd.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

(2043)

"Great hotel "

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

Hicham

CA $154

CA $216 total

includes taxes & fees

Nov 24 - Nov 25

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

![Egyptian cotton sheets, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/c12c78f1.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)

### Hyatt Centric The Loop Chicago

Theatre District, 6.7 km from Oakland

9.0/10

Wonderful

(2234)

"Clean room, nice staff"

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

Rosanna

CA $178

CA $209 total

includes taxes & fees

Nov 24 - Nov 25

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

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-22&endDate=2025-11-23&regionId=6132392&adults=2&sort=RECOMMENDED&openPlayBack=true)

## Hotels in Oakland with a pool

![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/20c3f16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/eaff657c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/d3f07aef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/e1eb307d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Royal Sonesta Chicago River North

River North, 7.8 km from Oakland

-   Pool
    

9.2/10

Wonderful

(2225)

CA $145

CA $215 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Hotel-Search?startDate=2025-12-07&endDate=2025-12-08&selected=3023837&PinnedHotelID=3023837&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)

![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)

![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)

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

River North, 7.7 km from Oakland

-   Pool
    

8.8/10

Excellent

(1980)

CA $136

CA $160 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-24&endDate=2025-11-25&selected=5467&PinnedHotelID=5467&HadPinnedHotel=true&regionId=6132392&adults=2&amenities=POOL&openPlayBack=true)

![Indoor pool, seasonal outdoor pool, free cabanas, sun loungers](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/8cd3425b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/8de272e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/02375ebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/416b9fb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Radisson Blu Aqua Hotel Chicago

7.1 km from Oakland

-   Pool
    

8.6/10

Excellent

(1744)

CA $197

CA $267 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-24&endDate=2025-11-25&selected=4520626&PinnedHotelID=4520626&HadPinnedHotel=true&regionId=6132392&adults=2&amenities=POOL&openPlayBack=true)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/3100/3009/008ccf4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/3100/3009/0f1d54eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/3100/3009/6e071111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3100/3009/70d02e59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Courtyard by Marriott Chicago Downtown River North

River North, 7.7 km from Oakland

-   Pool
    

8.6/10

Excellent

(1001)

CA $162

CA $190 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=3009&PinnedHotelID=3009&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

(1555)

CA $223

CA $304 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=12167&PinnedHotelID=12167&HadPinnedHotel=true&regionId=6132392&adults=2&amenities=POOL&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/42397db2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/5785af38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/fcdb86cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### InterContinental Chicago Magnificent Mile by IHG

Magnificent Mile, 7.7 km from Oakland

-   Pool
    

9.0/10

Wonderful

(2536)

CA $251

CA $340 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-24&endDate=2025-11-25&selected=20205&PinnedHotelID=20205&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)

![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)

![Ballroom](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/db08811d.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
    

8.4/10

Very good

(2718)

CA $127

CA $190 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Hotel-Search?startDate=2025-12-09&endDate=2025-12-10&selected=570329&PinnedHotelID=570329&HadPinnedHotel=true&regionId=6132392&adults=2&amenities=POOL&openPlayBack=true)

![Exterior](https://images.trvl-media.com/lodging/2000000/1120000/1110100/1110039/86b2dc93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1120000/1110100/1110039/289caf93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Tapas bar](https://images.trvl-media.com/lodging/2000000/1120000/1110100/1110039/e6c4a358.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1120000/1110100/1110039/0d2b3bd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### AC Hotels by Marriott Chicago Downtown

River North, 8 km from Oakland

-   Pool
    

8.8/10

Excellent

(1004)

CA $153

CA $180 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=1110039&PinnedHotelID=1110039&HadPinnedHotel=true&regionId=6132392&adults=2&amenities=POOL&openPlayBack=true)

![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/20000/19300/19215/bf025cd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/19300/19215/2b0f74d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/20000/19300/19215/1e5dfdc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/20000/19300/19215/7d7cea31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Renaissance Chicago Downtown Hotel

The Loop, 7.3 km from Oakland

-   Pool
    

9.2/10

Wonderful

(1002)

CA $240

CA $324 total

includes taxes & fees

Nov 26 - Nov 27

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-26&endDate=2025-11-27&selected=19215&PinnedHotelID=19215&HadPinnedHotel=true&regionId=6132392&adults=2&amenities=POOL&openPlayBack=true)

[See more properties](https://www.expedia.ca/Hotel-Search?startDate=2025-11-22&endDate=2025-11-23&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)

![Reception](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/5132819a.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 detail](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/cb4330d2.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

(2574)

CA $94

CA $136 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Hotel-Search?startDate=2025-12-08&endDate=2025-12-09&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)

![Exterior](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/2f70f55e.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)

### Hotel Riu Plaza Chicago

Streeterville, 7.9 km from Oakland

9.4/10

Exceptional

(2724)

CA $146

CA $211 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Hotel-Search?startDate=2025-12-08&endDate=2025-12-09&selected=102622712&PinnedHotelID=102622712&HadPinnedHotel=true&regionId=6132392&adults=2&guestRating=35&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)

![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/5496cb17.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/dd081548.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

(3324)

CA $146

CA $171 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-24&endDate=2025-11-25&selected=76459163&PinnedHotelID=76459163&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)

![View from room](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/d24507d4.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)

![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/07c9ead9.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

(3240)

CA $143

CA $168 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Hotel-Search?startDate=2025-12-07&endDate=2025-12-08&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true&regionId=6132392&adults=2&guestRating=35&openPlayBack=true)

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

![2 bars/lounges](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/55a8ba7b.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/58000000/57660000/57651200/57651125/5d460cc6.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

(2215)

CA $145

CA $218 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-25&endDate=2025-11-26&selected=57651125&PinnedHotelID=57651125&HadPinnedHotel=true&regionId=6132392&adults=2&guestRating=35&openPlayBack=true)

![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)

![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)

![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/c042bdff.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

8.4/10

Very good

(1417)

CA $156

CA $183 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=1346&PinnedHotelID=1346&HadPinnedHotel=true&regionId=6132392&adults=2&guestRating=35&openPlayBack=true)

![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)

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

![Reception](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/d7ae47e3.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)

### DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 7.8 km from Oakland

8.8/10

Excellent

(2129)

CA $134

CA $157 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=21152&PinnedHotelID=21152&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)

![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)

![Standard Room](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/22cb8b3e.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)

### Warwick Allerton - Chicago

Magnificent Mile, 8.1 km from Oakland

8.4/10

Very good

(2950)

CA $96

CA $153 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Hotel-Search?startDate=2025-12-07&endDate=2025-12-08&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)

![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.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

(2879)

CA $138

CA $162 total

includes taxes & fees

Nov 26 - Nov 27

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-26&endDate=2025-11-27&selected=26998765&PinnedHotelID=26998765&HadPinnedHotel=true&regionId=6132392&adults=2&guestRating=35&openPlayBack=true)

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

![Room, 1 King Bed, City View | View from room](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/c06f4b61.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)

![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)

### citizenM Chicago Downtown

Theatre District, 7.3 km from Oakland

9.2/10

Wonderful

(4064)

CA $160

CA $188 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Hotel-Search?startDate=2025-11-10&endDate=2025-11-11&selected=82652306&PinnedHotelID=82652306&HadPinnedHotel=true&regionId=6132392&adults=2&guestRating=35&openPlayBack=true)

[See more properties](https://www.expedia.ca/Hotel-Search?startDate=2025-11-22&endDate=2025-11-23&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

![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

"AB"

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

"Nice and easy check in. Clean room. Comfy bed. "

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

![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg)

### Congress Plaza Hotel

10/10 Excellent

"I absolutely love the antique Chicago vibes!"

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

![River Hotel](//images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg)

### River Hotel

10/10 Excellent

"Customer service "

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

"Loved the view from our room, syaff helpfull. Not much amenities but everything close by."

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

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

### Freehand Chicago

10/10 Excellent

"Everything was amazing "

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

![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg)

### Warwick Allerton - Chicago

10/10 Excellent

"Everything was nice and seamless!"

[](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.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

"Highly recommended! "

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

"The staff was friendly, the location was very convenient and the train was across the street. "

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

## Explore a world of travel with Expedia

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