Title: 10 Best Hotels in Oakland, Chicago for 2026 | Expedia.ca

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# Hotels in Oakland, Chicago 

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## Check prices for these dates

Tonight

[Jan 7 - Jan 8](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2026-01-07&endDate=2026-01-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 8 - Jan 9](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2026-01-08&endDate=2026-01-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Recommended

Price (low to high)

Distance

Star rating

## Our top choices for Oakland hotels

![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 restaurants, breakfast, lunch, dinner served; Latin American cuisine](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/cadeb422.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)

![Exterior](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/444bc42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Streeterville, 7.5 km from Oakland

9.4/10

Exceptional

(2328)

"Great stay!"

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

Angela

CA $139

CA $210 total

includes taxes & fees

Jan 13 - Jan 14

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

![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/w3995h2667x0y0-afbbbc14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

### The Wade

[](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information)

Streeterville, 7.9 km from Oakland

8.4/10

Very good

(1578)

"Easy check in and out, excellent room service and dining menu."

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

Kevin Bradford

CA $139

CA $163 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information)

![Indoor wedding](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/3cb3732b.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/1000000/20000/17300/17288/aa950453.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/1000000/20000/17300/17288/bebf91fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/32068350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Swissotel - Chicago

[](https://www.expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information)

7.2 km from Oakland

9.0/10

Wonderful

(3089)

"Amazing staff and location beautiful hotel "

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

RANDIE

CA $157

CA $225 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/da498d1e.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/ec33d4f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/2435ca6e.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)

### Embassy Suites by Hilton Chicago Downtown Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information)

Streeterville, 7.6 km from Oakland

8.2/10

Very good

(2813)

"Great hotel staff and location. "

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

Jacqueline

CA $120

CA $182 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information)

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

![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/a08c52fd.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)

![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

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

Streeterville, 7.8 km from Oakland

8.8/10

Excellent

(2221)

"Fantastic stay! Looking forward to staying here again!!"

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

Amber

CA $117

CA $138 total

includes taxes & fees

Jan 13 - Jan 14

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

![Lunch and dinner served](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/d70c748e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, seasonal outdoor pool, free cabanas, sun loungers](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/fd4d7555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/df6e8a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/w2880h1919x0y0-235561ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Radisson Blu Aqua Hotel Chicago

[](https://www.expedia.ca/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.Hotel-Information)

7.1 km from Oakland

8.6/10

Excellent

(1829)

"Great hotel"

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

Yavuz

CA $193

CA $262 total

includes taxes & fees

Jan 24 - Jan 25

[](https://www.expedia.ca/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Banquet hall](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/2ad62276.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/27000000/27000000/26998800/26998765/693d9c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/352e3b39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aloft Chicago Mag Mile

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

Streeterville, 7.9 km from Oakland

8.6/10

Excellent

(3014)

"Great place to stay"

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

Elisha

CA $115

CA $135 total

includes taxes & fees

Jan 21 - Jan 22

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

![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/9c44ca76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/3f6518d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/325381ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/9833019f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ivy Boutique Hotel

[](https://www.expedia.ca/Chicago-Hotels-Ivy-Boutique-Hotel.h5204897.Hotel-Information)

Streeterville, 7.9 km from Oakland

8.6/10

Excellent

(1068)

"My favorite hotel for a staycation"

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

SABRINA L

CA $105

CA $123 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Chicago-Hotels-Ivy-Boutique-Hotel.h5204897.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/4e2c019f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/db8ea890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/w3839h3333x0y0-56c69498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/da2c2cd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

[](https://www.expedia.ca/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Downtown.h25929.Hotel-Information)

Streeterville, 8.6 km from Oakland

8.6/10

Excellent

(2324)

"Recommend it for Lake view and decent breakfast"

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

Caifang

CA $135

CA $158 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Downtown.h25929.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/580000/571400/571328/357f9e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/580000/571400/571328/2ee04c4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/1000000/580000/571400/571328/7163999b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/1000000/580000/571400/571328/5a6cccaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Fairfield-Inn-Suites-Chicago-Downtown-Magnificent-Mile.h571328.Hotel-Information)

Streeterville, 7.9 km from Oakland

9.0/10

Wonderful

(1028)

"Great location, friendly staff, clean rooms"

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

Jared

CA $123

CA $144 total

includes taxes & fees

Jan 12 - Jan 13

[](https://www.expedia.ca/Chicago-Hotels-Fairfield-Inn-Suites-Chicago-Downtown-Magnificent-Mile.h571328.Hotel-Information)

![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3840h2559x0y3-c577bf94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/fb110cc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Lake View](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2561x3y0-ec3252d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3840h1497x0y3-3b277bb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Regency Chicago

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information)

The Loop, 7.3 km from Oakland

9.4/10

Exceptional

(3452)

"The Hotel was amazing great location "

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

Donnisha

CA $211

CA $289 total

includes taxes & fees

Jan 24 - Jan 25

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information)

![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)

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

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

![42-inch flat-screen TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f5951ad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Chicago/Magnificent Mile Suites

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

Streeterville, 8.6 km from Oakland

9.0/10

Wonderful

(3671)

"Great hotel!"

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

William

CA $123

CA $145 total

includes taxes & fees

Jan 25 - Jan 26

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

![City view](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/cf0663e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/f64fa789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/1a16c1e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/dc6ab106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Millennium Knickerbocker Chicago

[](https://www.expedia.ca/Chicago-Hotels-Millennium-Knickerbocker-Chicago.h15087.Hotel-Information)

Streeterville, 8.6 km from Oakland

8.6/10

Excellent

(2006)

"Very clean, quiet, and warm reception and service from the staff. "

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

tim

CA $123

CA $176 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Chicago-Hotels-Millennium-Knickerbocker-Chicago.h15087.Hotel-Information)

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

![Deluxe Room, 1 King Bed with Sofa bed, Corner](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/e4e07af2.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/1000000/160000/151200/151139/6234383e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/3a5d3e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Centric Chicago Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information)

Streeterville, 8 km from Oakland

9.0/10

Wonderful

(1062)

"Amazing location, excellent service and great pool and hot tub. "

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

Tim

CA $135

CA $199 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information)

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

![Lobby](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/7c24871d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Exterior](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/a2db9cb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Courtyard by Marriott Chicago Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information)

Streeterville, 7.9 km from Oakland

9.0/10

Wonderful

(1661)

"Would definitely stay again…location was perfect "

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

Ashley

CA $139

CA $164 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/37fa1971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/67428c96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor wedding area](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/e3571b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/c476053d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Chicago Hotel Collection - Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information)

Streeterville, 8.2 km from Oakland

7.6/10

Good

(1167)

"Clean rooms. Great amenities. Great price. "

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

Alondra

CA $155

CA $182 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.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)

![Lobby](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/cc779b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges, rooftop bar](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/w2990h1178x0y0-a3dcd2ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/w1201h1722x0y78-8f9c452e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Riu Plaza Chicago

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

Streeterville, 7.9 km from Oakland

9.4/10

Exceptional

(3121)

"Second time to stay here, everything is great!"

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

Wei

CA $125

CA $186 total

includes taxes & fees

Jan 8 - Jan 9

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

![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)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/c33b753e.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)

### Best Western Grant Park Hotel

[](https://www.expedia.ca/Chicago-Hotels-Best-Western-Grant-Park-Hotel.h23023.Hotel-Information)

The Loop, 5.4 km from Oakland

8.2/10

Very good

(2664)

"Clean room, good location and service. "

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

Jolanta

CA $98

CA $115 total

includes taxes & fees

Jan 12 - Jan 13

[](https://www.expedia.ca/Chicago-Hotels-Best-Western-Grant-Park-Hotel.h23023.Hotel-Information)

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

![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/086ff612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Junior Suite, City View | City view](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/3e0e58e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Congress Plaza Hotel

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

The Loop, 6 km from Oakland

8.0/10

Very good

(9781)

"Wonderful stay!"

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

Zach

CA $115

CA $135 total

includes taxes & fees

Jan 8 - Jan 9

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

![Lobby lounge](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/f13a5c54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/81673aca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![City view](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/de4336b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/6e228b75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Le Méridien Essex Chicago

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Essex-Chicago.h35130365.Hotel-Information)

The Loop, 5.6 km from Oakland

8.8/10

Excellent

(1007)

"Great stay for quick weekend trip "

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

Natali

CA $114

CA $158 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Chicago-Hotels-Hotel-Essex-Chicago.h35130365.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=2026-01-21&endDate=2026-01-22&regionId=6132392&adults=2&sort=RECOMMENDED&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
- Theatre District

![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 rides](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23717-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Chicago which includes skyline, cbd and landscape views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23710-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Chicago featuring theatre scenes, a city and street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23730-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Frank Lloyd Wright Home and Studio which includes interior views and a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26627-Frank-Lloyd-Wright-Home-And-Studio.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Chicago featuring night scenes, rides and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23718-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=651190586167894016)

![Theatre District map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:mxs%7EF%7E%7EzuOa%40wb%40mAwCKcDmHiMl%7B%40MZry%40_o%40v%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=wPQBnQtd4sat1wXcy-Q0SbgXS1s=)

### Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line). 

[See properties](https://www.expedia.ca/Hotel-Search?regionId=651190586167894016)

## Top Oakland Hotel Reviews

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg)

### Hilton Chicago

10/10 Excellent

"BEAUTIFUL PLACE"

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

![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg)

### Hyatt Regency Chicago

10/10 Excellent

"Very nice hotel, great service, very convenient for travelers and family tour!"

[](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information)

![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg)

### Pendry Chicago

10/10 Excellent

"Everything was exceptional!!!!!"

[](https://expedia.ca/Chicago-Hotels-Pendry-Chicago.h982552.Hotel-Information)

![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg)

### Palmer House a Hilton Hotel

10/10 Excellent

"What stood out from Palmers house hotel for me was how spacious the rooms were! I got a 2 bed for 4 guests and we all fit perfectly with luggage and all , everyone accommodated easily :) "

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

![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg)

### Club Quarters Hotel Wacker at Michigan, Chicago

10/10 Excellent

"Helpful staff Great view of the River "

[](https://expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information)

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

### Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Yes"

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

![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg)

### Swissotel - Chicago

10/10 Excellent

"Everything was perfect from the room to the service and location. Definitely a great option when you visit Chicago "

[](https://expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information)

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

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

10/10 Excellent

"It was incredible! Service, room, and overall hotel were 10/10!"

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

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg)

### Eurostars Magnificent Mile

10/10 Excellent

"We got a free upgrade to deluxe room. Spacious room, nice big shower. Only dislike is there’s no shower door, it’s the open shower."

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

## Frequently asked questions

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

> 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?

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

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

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

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

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

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