
Hotels in Oakland, Chicago
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Our top choices for Oakland hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by HiltonStreeterville, 7.5 km from Oakland
9.4 out of 10, Exceptional, (2,545 reviews)
The price is CA $309
CA $416 total
includes taxes & fees
Jul 2 - Jul 3

Omni Chicago Hotel
Omni Chicago HotelStreeterville, 8.1 km from Oakland
9.2 out of 10, Wonderful, (1,807 reviews)
The price is CA $179
CA $259 total
includes taxes & fees
Jul 1 - Jul 2

Palmer House a Hilton Hotel
Palmer House a Hilton HotelTheatre District, 6.7 km from Oakland
8.6 out of 10, Excellent, (2,507 reviews)
The price is CA $257
CA $347 total
includes taxes & fees
Jul 2 - Jul 3

Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,510 reviews)
The price is CA $284
CA $388 total
includes taxes & fees
Jul 2 - Jul 3

Swissotel - Chicago
Swissotel - Chicago7.2 km from Oakland
9.0 out of 10, Wonderful, (3,382 reviews)
The price is CA $246
CA $342 total
includes taxes & fees
Jul 1 - Jul 2

Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (4,436 reviews)
The price is CA $224
CA $306 total
includes taxes & fees
Jul 6 - Jul 7

Sheraton Grand Chicago Riverwalk
Sheraton Grand Chicago RiverwalkStreeterville, 7.4 km from Oakland
8.6 out of 10, Excellent, (1,667 reviews)
The price is CA $279
CA $381 total
includes taxes & fees
Jul 2 - Jul 3

Congress Plaza Hotel
Congress Plaza HotelThe Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,265 reviews)
The price is CA $190
CA $226 total
includes taxes & fees
Jun 29 - Jun 30

Eurostars Magnificent Mile
Eurostars Magnificent MileRiver North, 8.1 km from Oakland
9.0 out of 10, Wonderful, (3,644 reviews)
The price is CA $201
CA $239 total
includes taxes & fees
Jul 2 - Jul 3

Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium ParkThe Loop, 7.1 km from Oakland
8.8 out of 10, Excellent, (2,196 reviews)
The price is CA $301
CA $407 total
includes taxes & fees
Jul 7 - Jul 8

LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonThe Loop, 7.4 km from Oakland
9.4 out of 10, Exceptional, (3,737 reviews)
The price is CA $295
CA $391 total
includes taxes & fees
Jul 1 - Jul 2

Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago DowntownTheatre District, 6.7 km from Oakland
9.4 out of 10, Exceptional, (2,253 reviews)
The price is CA $171
CA $246 total
includes taxes & fees
Jul 5 - Jul 6

Hilton Chicago
Hilton ChicagoThe Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,867 reviews)
The price is CA $274
CA $367 total
includes taxes & fees
Jul 1 - Jul 2

Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The LoopTheatre District, 6.9 km from Oakland
9.4 out of 10, Exceptional, (1,099 reviews)
The price is CA $194
CA $272 total
includes taxes & fees
Jul 6 - Jul 7

Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago7.1 km from Oakland
8.6 out of 10, Excellent, (1,965 reviews)
The price is CA $282
CA $378 total
includes taxes & fees
Jul 1 - Jul 2

The Royal Sonesta Chicago Downtown
The Royal Sonesta Chicago DowntownThe Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,464 reviews)
The price is CA $243
CA $334 total
includes taxes & fees
Jul 5 - Jul 6

citizenM Chicago Downtown
citizenM Chicago DowntownTheatre District, 7.3 km from Oakland
9.4 out of 10, Exceptional, (4,331 reviews)
The price is CA $225
CA $268 total
includes taxes & fees
Jul 1 - Jul 2

The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold CoastGold Coast, 9.4 km from Oakland
8.2 out of 10, Very good, (1,602 reviews)
The price is CA $215
CA $256 total
includes taxes & fees
Jul 5 - Jul 6

Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South LoopThe Loop, 5.4 km from Oakland
8.8 out of 10, Excellent, (2,042 reviews)
The price is CA $205
CA $244 total
includes taxes & fees
Jul 1 - Jul 2

Warwick Allerton - Chicago
Warwick Allerton - ChicagoStreeterville, 8.1 km from Oakland
8.6 out of 10, Excellent, (3,062 reviews)
The price is CA $183
CA $258 total
includes taxes & fees
Jul 5 - Jul 6
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.
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most.

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.

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.

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.

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.

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.
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