Oakland Hotels, 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, (2,529 reviews)
"Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"
Deborah
The price is AU$415
includes taxes & fees
1 July - 2 July
Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,503 reviews)
"Staff was great."
Marianne
The price is AU$415
includes taxes & fees
5 July - 6 July
Hilton Chicago
Hilton ChicagoThe Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,844 reviews)
"great hotel and excellent to stay"
Ruben
The price is AU$445
includes taxes & fees
30 June - 1 July
Omni Chicago Hotel
Omni Chicago HotelStreeterville, 8.1 km from Oakland
9.2 out of 10, Wonderful, (1,793 reviews)
"Great place at a great location."
Alejandro
The price is AU$316
includes taxes & fees
1 July - 2 July
Congress Plaza Hotel
Congress Plaza HotelThe Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,203 reviews)
"Great stay thanks"
Felipa
The price is AU$229
includes taxes & fees
29 June - 30 June
Sheraton Grand Chicago Riverwalk
Sheraton Grand Chicago RiverwalkStreeterville, 7.4 km from Oakland
8.6 out of 10, Excellent, (1,658 reviews)
"Excellent location."
Mirna
The price is AU$387
includes taxes & fees
2 July - 3 July
The Blackstone, Autograph Collection
The Blackstone, Autograph CollectionThe Loop, 5.8 km from Oakland
9.0 out of 10, Wonderful, (1,005 reviews)
"Great location, clean hotel, and very accommodating staff."
Neydee
The price is AU$303
includes taxes & fees
1 July - 2 July
Swissotel - Chicago
Swissotel - Chicago7.2 km from Oakland
9.0 out of 10, Wonderful, (3,370 reviews)
"Nice Hotel, rooms are clean , the best for us was the location, i would recommend"
Sergio
The price is AU$346
includes taxes & fees
5 July - 6 July
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago DowntownTheatre District, 6.7 km from Oakland
9.2 out of 10, Wonderful, (2,255 reviews)
"Great location"
Gabino
The price is AU$235
includes taxes & fees
5 July - 6 July
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (4,380 reviews)
"The breakfast, location, and staff were amazing."
Corey
The price is AU$359
includes taxes & fees
30 June - 1 July
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonThe Loop, 7.4 km from Oakland
9.4 out of 10, Exceptional, (3,732 reviews)
"Great location, excellent room and amenities proactively attentive staff."
Robert
The price is AU$440
includes taxes & fees
30 June - 1 July
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Bluegreen Vacations Hotel Blake, an Ascend Collection HotelThe Loop, 6.1 km from Oakland
9.6 out of 10, Exceptional, (1,251 reviews)
"Overall comfortable stay and easy access by walk to downtown and all other places in the city."
raghu
The price is AU$282
includes taxes & fees
1 July - 2 July
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesStreeterville, 8.6 km from Oakland
9.0 out of 10, Wonderful, (4,392 reviews)
"Great stay!"
Avradita
The price is AU$271
includes taxes & fees
2 July - 3 July
Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The LoopTheatre District, 6.9 km from Oakland
9.4 out of 10, Exceptional, (1,085 reviews)
"Such a lovely hotel with a beautiful, excellent staff, and lots of character!"
Debby
The price is AU$277
includes taxes & fees
6 July - 7 July
Arlo Chicago
Arlo ChicagoTheatre District, 7.1 km from Oakland
9.4 out of 10, Exceptional, (2,129 reviews)
"Excellent location and welcoming staff."
Tammy
The price is AU$344
includes taxes & fees
5 July - 6 July
Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago7.1 km from Oakland
8.6 out of 10, Excellent, (1,955 reviews)
"Great Hotel "
Dylan
The price is AU$399
includes taxes & fees
1 July - 2 July
River Hotel
River HotelThe Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,240 reviews)
"Location is great and staff is very nice and helpful"
Deborah
The price is AU$218
includes taxes & fees
5 July - 6 July
Eurostars Magnificent Mile
Eurostars Magnificent MileRiver North, 8.1 km from Oakland
9.0 out of 10, Wonderful, (3,622 reviews)
"Had an amazing stay here!"
Audrey
The price is AU$270
includes taxes & fees
1 July - 2 July
The Royal Sonesta Chicago Downtown
The Royal Sonesta Chicago DowntownThe Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,446 reviews)
"Great location, nice property, helpful staff, and spacious, comfortable rooms."
Sunil
The price is AU$373
includes taxes & fees
1 July - 2 July
Sports Illustrated Resorts Chicago
Sports Illustrated Resorts ChicagoTheatre District, 7.2 km from Oakland
9.2 out of 10, Wonderful, (1,405 reviews)
"The location does not get better. That room was quiet despite the train running outside Hotel is located within a walk-in distance to all the major attractions . Great and convenient location."
Flora
The price is AU$411
includes taxes & fees
6 July - 7 July
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.
Our guide on where to stay in Oakland
Find the best Oakland areas for the activities you enjoy most. Learn more about Oakland
Learn more about Oakland
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
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
The Loop
Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
