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May 22 - May 24
Next weekend
May 29 - May 31

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Our top choices for Oakland hotels

Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 7.5 km from Oakland
9.4 out of 10, Exceptional, (2,507 reviews)
"I loved it here and will definitely stay again."
United States
Gina
The price is ￥28,394
￥39,244 total
includes taxes & fees
May 26 - May 27
Sable at Navy Pier Chicago, Curio Collection by Hilton
Indoor pool

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 6.7 km from Oakland
8.6 out of 10, Excellent, (2,459 reviews)
"My favorite place to stay!"
United States
Teresa
The price is ￥29,218
￥39,466 total
includes taxes & fees
May 26 - May 27
Palmer House a Hilton Hotel
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 8.1 km from Oakland
9.0 out of 10, Wonderful, (3,552 reviews)
"Great location, large rooms, we loved our stay and would definitely recommend "
Australia
Belinda
The price is ￥25,451
￥30,259 total
includes taxes & fees
May 25 - May 26
Eurostars Magnificent Mile
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,332 reviews)
"Wonderful location right on the river. Fitness area wonderful, staff helpful. Would stay again!"
United States
Saleem
The price is ￥26,650
￥37,285 total
includes taxes & fees
May 25 - May 26
Swissotel - Chicago
Executive lounge

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 7.1 km from Oakland
8.8 out of 10, Excellent, (2,162 reviews)
"Great place"
United States
JOSE
The price is ￥27,926
￥38,876 total
includes taxes & fees
May 25 - May 26
Fairmont Chicago at Millennium Park
Lobby

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 6.7 km from Oakland
9.2 out of 10, Wonderful, (2,240 reviews)
"Close to many attractions and shopping and nice unique hotel"
United States
Brittany
The price is ￥16,231
￥24,151 total
includes taxes & fees
May 25 - May 26
Silversmith Hotel Chicago Downtown
Room service - dining

The Wade

The Wade
4.5 star property
Streeterville, 7.9 km from Oakland
8.4 out of 10, Very Good, (1,834 reviews)
"Excellent location, clean modern rooms."
United States
Molly
The price is ￥24,179
￥28,747 total
includes taxes & fees
May 25 - May 26
The Wade
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very Good, (10,166 reviews)
"The bar was very welcoming and the historic ambience and location was exceptional"
United States
Patricia
The price is ￥21,245
￥25,258 total
includes taxes & fees
May 26 - May 27
Congress Plaza Hotel
Lobby

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,251 reviews)
"Nice place to stay"
United States
Jimmie
The price is ￥25,292
￥30,072 total
includes taxes & fees
May 26 - May 27
Aloft by Marriott Chicago Mag Mile
Lobby

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 9.4 km from Oakland
8.2 out of 10, Very Good, (1,468 reviews)
"A nice stay and lovely location. "
United States
Robin
The price is ￥24,466
￥29,088 total
includes taxes & fees
Jun 3 - Jun 4
The Chicago Hotel Collection Ambassador Gold Coast
2 restaurants, breakfast, lunch, dinner served; American cuisine

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 7.4 km from Oakland
9.4 out of 10, Exceptional, (3,713 reviews)
"I had a great stay and would book again."
United States
Brandi
The price is ￥31,175
￥41,732 total
includes taxes & fees
May 26 - May 27
LondonHouse Chicago, Curio Collection by Hilton
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,802 reviews)
"Great staff and location. "
United States
Robert
The price is ￥25,957
￥35,530 total
includes taxes & fees
May 26 - May 27
Hilton Chicago
2 bars/lounges

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,524 reviews)
"Very good place to stay. I really liked the lobby — it’s very spacious. The lobby design is also very open and artistic."
Canada
Tong
The price is ￥34,836
￥47,090 total
includes taxes & fees
May 25 - May 26
Hyatt Regency Chicago
2 bars/lounges

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 7.4 km from Oakland
8.6 out of 10, Excellent, (1,623 reviews)
"It was very clean, beautiful place"
United States
Grisel
The price is ￥34,216
￥46,354 total
includes taxes & fees
May 25 - May 26
Sheraton Grand Chicago Riverwalk
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (4,189 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is ￥23,701
￥32,713 total
includes taxes & fees
May 25 - May 26
Hotel Riu Plaza Chicago
Studio, 2 Double Beds | Bathroom | Shower, free toiletries, hair dryer, towels

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Theatre District, 7.2 km from Oakland
9.2 out of 10, Wonderful, (1,405 reviews)
"Nice location nestled I'm the middle of it all. Great stay the staff was communicative."
United States
Erik
The price is ￥27,675
￥37,377 total
includes taxes & fees
May 25 - May 26
Sports Illustrated Resorts Chicago
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 8.2 km from Oakland
7.8 out of 10, Good, (1,436 reviews)
"Great stay"
United States
Christa
The price is ￥19,286
￥22,928 total
includes taxes & fees
May 25 - May 26
The Chicago Hotel Collection - Magnificent Mile
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 6.9 km from Oakland
9.4 out of 10, Exceptional, (1,072 reviews)
"Clean rooms, comfy bed."
United States
Brenda
The price is ￥25,292
￥34,790 total
includes taxes & fees
May 25 - May 26
Staypineapple, An Iconic Hotel, The Loop
Restaurant

Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Theatre District, 6.8 km from Oakland
9.0 out of 10, Wonderful, (2,550 reviews)
"Lovely place to stay in a great location in the city."
United States
Rachel
The price is ￥23,633
￥32,078 total
includes taxes & fees
May 25 - May 26
Hyatt Centric The Loop Chicago
Lobby

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,197 reviews)
"excellent stay"
United States
Jaeyoung
The price is ￥20,146
￥23,950 total
includes taxes & fees
May 25 - May 26
River Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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.

Panoramic view of Lincoln Park and the Chicago skyline.

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.

Top Oakland Hotel Reviews

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

6/10 Okay
"The room was clean but pretty basic. It was good overall but we did have an issue with the a/c switching off in the middle of the night. Unfortunately the hotel didn’t have any fans to remedy that situation. Other than that we had a very enjoyable stay. The location is great! "
Madan 3-night trip
Posted 2 hours ago
Hotel Felix River North/Magnificent Mile

Frequently asked questions

What's it like in Oakland?
Oakland is a neighborhood that travelers like for its beaches, restaurants, and shopping. Looking for sights you might find in a travel guide about Oakland? Consider a visit to Lake Michigan while you're in the neighborhood.
How many hotels are there in the Oakland area?
When you want to find places to stay in Chicago, start by booking one of Expedia's 6 hotels and other accommodations in Oakland.
If I need to cancel my hotel reservation in Oakland, will I receive a refund?
Yes, most hotel bookings are fully refundable if you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you have a non-refundable reservation, you might still have the option to cancel and receive a refund within a 24-hour period of booking. Plug in your dates, click on "Search", then filter by "fully refundable" to review the best deals in Oakland.
Where can I learn more about changing or cancelling my trip to Oakland?
To find more details about picking new dates or cancelling your trip to Oakland, go to https://www.expedia.com/service/.
What can I see and do in this Chicago neighborhood?
Spend some time exploring the natural setting of Oakland with a visit to Lake Michigan and Burnham Park. A visit to 41st Street Beach is also worth the trip while you're discovering the neighborhood. A few places to visit in the area around Oakland include Soldier Field, Nat King Cole Residence, and Muddy Waters' House. While you're out sightseeing, Ida B. Wells-Barnett Residence and Ida B Wells House are a couple of additional sights to visit in Chicago.

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