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Jul 30 - Jul 31
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Aug 1 - Aug 3
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Discover 4,547 Oakland hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Sable at Navy Pier Chicago, Curio Collection by Hilton
Relax in style with lounge chairs and bar stools amidst a scenic backdrop.

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2076)
"Beautiful property, will definitely stay there again."
The price is NT$5,820
NT$7,693 total
includes taxes & fees
Aug 21 - Aug 22
Sable at Navy Pier Chicago, Curio Collection by Hilton
The Wade
Enjoy a sea view from the large window, with a comfortable seating area and unique artwork on display.

The Wade

4.5 star property
8.2 out of 10, Very Good, (1134)
"It was a very relaxing stay and amazing view!"
The price is NT$3,979
NT$4,671 total
includes taxes & fees
Aug 17 - Aug 18
The Wade
Swissotel - Chicago
Enjoy a panoramic city view from this stylish room, featuring a spacious dining area with a round table and six comfortable chairs.

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2520)
"Best location to stay "
The price is NT$5,570
NT$7,407 total
includes taxes & fees
Aug 19 - Aug 20
Swissotel - Chicago
Loews Chicago Hotel
Hotel entrance with a prominent sign and contemporary design.

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1521)
"This is a nice hotel in a great neighborhood. "
The price is NT$5,910
NT$7,879 total
includes taxes & fees
Aug 17 - Aug 18
Loews Chicago Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
Relax by the pool surrounded by lounge chairs and umbrellas, taking in the city skyline views.

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1937)
"Very pleasant stay!"
The price is NT$4,760
NT$5,588 total
includes taxes & fees
Aug 21 - Aug 22
DoubleTree by Hilton Chicago - Magnificent Mile
Radisson Blu Aqua Hotel Chicago
Relax by the rectangular pool with marked lanes, surrounded by sun loungers and a seating area.

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.4 out of 10, Very Good, (1570)
"Amazing place!"
The price is NT$5,462
NT$7,318 total
includes taxes & fees
Aug 17 - Aug 18
Radisson Blu Aqua Hotel Chicago
Fairmont Chicago at Millennium Park
Enjoy a meal in the kitchen with a large island and dining area, offering a view of the city skyline.

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1814)
"Excellent accommodation, very clean and friendly staff "
The price is NT$6,896
NT$8,963 total
includes taxes & fees
Aug 24 - Aug 25
Fairmont Chicago at Millennium Park
Aloft Chicago Mag Mile
Conference room with a large, round table and six chairs, offering city views.

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2773)
"Great location and friendly staff"
The price is NT$4,247
NT$4,985 total
includes taxes & fees
Aug 10 - Aug 11
Aloft Chicago Mag Mile
Ivy Boutique Hotel
Stunning city views from a sleek, high-rise building with a dynamic design and lush greenery.

Ivy Boutique Hotel

4.5 star property
8.8 out of 10, Excellent, (1019)
"Great location and hotel "
The price is NT$5,023
NT$5,897 total
includes taxes & fees
Aug 5 - Aug 6
Ivy Boutique Hotel
Hyatt Regency Chicago
2 bars/lounges

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3358)
"Great stay for a short weekend"
The price is NT$6,638
NT$8,661 total
includes taxes & fees
Aug 22 - Aug 23
Hyatt Regency Chicago
Hilton Chicago/Magnificent Mile Suites
Enjoy a sophisticated dining experience with a beautifully set table and city view.

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2538)
"Great location and hotel!"
The price is NT$4,266
NT$5,008 total
includes taxes & fees
Aug 17 - Aug 18
Hilton Chicago/Magnificent Mile Suites
Millennium Knickerbocker Chicago
Experience the grandeur of our lobby, featuring a stunning chandelier, comfortable seating, and a beautiful staircase.

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1902)
"Great stay"
The price is NT$3,757
NT$5,105 total
includes taxes & fees
Aug 24 - Aug 25
Millennium Knickerbocker Chicago
Hyatt Centric Chicago Magnificent Mile
Room, 1 King Bed, Corner | Premium bedding, pillowtop beds, in-room safe, desk

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1023)
"Best place we have stayed in Chicago in a long time. "
The price is NT$4,752
NT$6,449 total
includes taxes & fees
Aug 17 - Aug 18
Hyatt Centric Chicago Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile
Relax in a serene urban setting with a spacious seating area and unobstructed city views.

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.2 out of 10, Good, (1115)
"Enjoyed staying here!"
The price is NT$1,201
NT$5,575 total
includes taxes & fees
Aug 6 - Aug 7
The Chicago Hotel Collection - Magnificent Mile
Hotel Saint Clair- Magnificent Mile
Enjoy meals around the central dining table, surrounded by comfortable chairs and a display case.

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very Good, (1711)
"I really enjoyed my stay here, the staff was very pleasant and the rooms great!"
Hotel Saint Clair- Magnificent Mile
The Blackstone, Autograph Collection
Experience the grandeur of this opulent hall with its high ceiling, patterned carpet, and arched windows.

The Blackstone, Autograph Collection

4.0 star property
9.0 out of 10, Wonderful, (1000)
"Pleasant with great views and a good restaurant."
The price is NT$5,747
NT$7,614 total
includes taxes & fees
Aug 7 - Aug 8
The Blackstone, Autograph Collection
Best Western Grant Park Hotel
Relax in a stylish seating area with plush armchairs and a decorative partition, surrounded by ambient lighting and a patterned rug.

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very Good, (2561)
"Excellent Hotel!!"
The price is NT$3,646
NT$4,280 total
includes taxes & fees
Aug 24 - Aug 25
Best Western Grant Park Hotel
Congress Plaza Hotel
Experience grandeur in this beautifully designed ballroom with high ceilings, arched windows, and elegant table settings.

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (9038)
"Great place to stay."
The price is NT$5,248
NT$6,160 total
includes taxes & fees
Aug 4 - Aug 5
Congress Plaza 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. Learn more about Oakland
Learn more about Oakland
Downtown Chicago showing a city
Downtown Chicago map

Downtown Chicago

5 out of top 10 points of interest in this area

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 - River North
Magnificent Mile map

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 - Downtown which includes a river or creek
The Loop map

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 showing railway items, street scenes and a city
River North map

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.

Chicago which includes modern architecture and a city
Lincoln Park map

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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"It is renovated, it is very clean, the breakfast was delicious"
GABRIELA 2-night trip
Posted 6 hours ago
Crowne Plaza Chicago West Loop by IHG

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 5 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.