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Aug 29 - Aug 30
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Aug 30 - Aug 31
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Aug 29 - Aug 31
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Sep 5 - Sep 7

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Discover 4,656 Oakland hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Our top choices for Oakland hotels

Holiday Inn Express Chicago - Magnificent Mile by IHG
Exterior

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 star property
8.4 out of 10, Very Good, (1021)
"Great hotel! "
The price is NT$4,249
NT$4,988 total
includes taxes & fees
Sep 3 - Sep 4
Holiday Inn Express Chicago - Magnificent Mile by IHG
Claridge House
Cocktail bar

Claridge House

4.0 star property
8.8 out of 10, Excellent, (1343)
"Great stay highly recommend!! "
The price is NT$7,672
NT$9,903 total
includes taxes & fees
Aug 31 - Sep 1
Claridge House
River Hotel
Lobby

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4593)
"Great place to stay, staff was very friendly"
The price is NT$4,553
NT$5,344 total
includes taxes & fees
Sep 1 - Sep 2
River Hotel
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2361)
"The best hotel, excellent breakfast, excellent location!!!"
The price is NT$4,206
NT$5,798 total
includes taxes & fees
Sep 2 - Sep 3
Hotel Riu Plaza Chicago
La Quinta Inn & Suites by Wyndham Chicago Downtown
Exterior

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
8.6 out of 10, Excellent, (2521)
"Had a wonderful stay here and staff was super friendly!"
The price is NT$4,097
NT$5,348 total
includes taxes & fees
Sep 1 - Sep 2
La Quinta Inn & Suites by Wyndham Chicago Downtown
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2109)
"Great place to stay!"
The price is NT$5,719
NT$7,600 total
includes taxes & fees
Sep 1 - Sep 2
Sable at Navy Pier Chicago, Curio Collection by Hilton
The Emily Hotel
Exterior

The Emily Hotel

4.0 star property
9.2 out of 10, Wonderful, (1194)
"Friendly staff, rooms very clean, food was excellent "
The price is NT$5,161
NT$6,058 total
includes taxes & fees
Sep 1 - Sep 2
The Emily Hotel
Residence Inn Chicago Downtown Magnificent Mile
Aerial view

Residence Inn Chicago Downtown Magnificent Mile

4.0 star property
9.6 out of 10, Exceptional, (333)
"Great experience and great hotel "
The price is NT$6,386
NT$7,496 total
includes taxes & fees
Sep 1 - Sep 2
Residence Inn Chicago Downtown Magnificent Mile
Hotel Felix River North/Magnificent Mile
Lobby sitting area

Hotel Felix River North/Magnificent Mile

4.0 star property
8.2 out of 10, Very Good, (2103)
"Great spot, good location, nice rooms. "
Hotel Felix River North/Magnificent Mile
Pendry Chicago
View from property

Pendry Chicago

4.5 star property
9.4 out of 10, Exceptional, (1066)
"Wonderful Stay."
The price is NT$7,184
NT$9,690 total
includes taxes & fees
Sep 21 - Sep 22
Pendry Chicago
The Chicago Hotel Collection Ambassador Gold Coast
Terrace/patio

The Chicago Hotel Collection Ambassador Gold Coast

4.0 star property
8.2 out of 10, Very Good, (1094)
"Great place to stay, would definitely recommend and stay here again "
The price is NT$3,918
NT$4,600 total
includes taxes & fees
Sep 3 - Sep 4
The Chicago Hotel Collection Ambassador Gold Coast
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Exterior

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

4.0 star property
9.6 out of 10, Exceptional, (1028)
"Great stay, highly recommended"
The price is NT$5,356
NT$6,287 total
includes taxes & fees
Sep 22 - Sep 23
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (9063)
"Family had a great stay. "
The price is NT$6,022
NT$7,069 total
includes taxes & fees
Sep 15 - Sep 16
Congress Plaza Hotel
Fairmont Chicago at Millennium Park
Executive lounge

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1887)
"Great location, staff is lovely!"
The price is NT$8,222
NT$10,549 total
includes taxes & fees
Sep 20 - Sep 21
Fairmont Chicago at Millennium Park
voco Chicago Downtown - Riverwalk by IHG
Bar (on property)

voco Chicago Downtown - Riverwalk by IHG

3.5 star property
8.8 out of 10, Excellent, (3025)
"Convenient location, nice staff and clean rooms. "
The price is NT$5,255
NT$6,169 total
includes taxes & fees
Sep 4 - Sep 5
voco Chicago Downtown - Riverwalk by IHG
Level Chicago Fulton Market
Executive lounge

Level Chicago Fulton Market

4.0 star property
9.2 out of 10, Wonderful, (274)
"The staff was excellent the amenities were a fantastic overall a great experience "
The price is NT$6,897
NT$8,777 total
includes taxes & fees
Sep 2 - Sep 3
Level Chicago Fulton Market
Virgin Hotels Chicago
Rooftop terrace

Virgin Hotels Chicago

4.5 star property
9.2 out of 10, Wonderful, (1352)
"Great area. Friendly and helpful staff. The beds are incredibly comfortable!"
The price is NT$9,136
NT$11,621 total
includes taxes & fees
Sep 1 - Sep 2
Virgin Hotels Chicago
Hyatt House Chicago West Loop
City view from property

Hyatt House Chicago West Loop

3.5 star property
8.8 out of 10, Excellent, (1024)
"Perfect location"
The price is NT$5,778
NT$6,783 total
includes taxes & fees
Sep 1 - Sep 2
Hyatt House Chicago West Loop
The Whitehall Hotel, BW Premier Collection
1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

The Whitehall Hotel, BW Premier Collection

3.5 star property
8.2 out of 10, Very Good, (3580)
"Great location, lovely room, clean, helpful staff."
The price is NT$3,390
NT$3,979 total
includes taxes & fees
Sep 3 - Sep 4
The Whitehall Hotel, BW Premier Collection
Silversmith Hotel Chicago Downtown
Lobby

Silversmith Hotel Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (1964)
"Great room and close to attractions "
Silversmith Hotel Chicago Downtown
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. Learn more about Oakland
Learn more about Oakland
Downtown Chicago showing a city

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

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

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

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

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

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.