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Discover 4,472 Oakland hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (3063)
"Perfect location, walkable to many restaurants and shops"
The price is ₩164,060
₩192,591 total
includes taxes & fees
Nov 4 - Nov 5
Eurostars Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2077)
"Great hotel"
The price is ₩223,923
₩262,862 total
includes taxes & fees
Nov 2 - Nov 3
DoubleTree by Hilton Chicago - Magnificent Mile
Aloft Chicago Mag Mile
Cocktail bar

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2846)
"Had a great stay!"
The price is ₩206,763
₩242,719 total
includes taxes & fees
Nov 2 - Nov 3
Aloft Chicago Mag Mile
River Hotel
Reception

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4717)
"Staff friendly and helpful..and accommodations just right..great location! "
The price is ₩184,455
₩216,531 total
includes taxes & fees
Nov 6 - Nov 7
River Hotel
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, (2170)
"Great hotel "
The price is ₩268,932
₩356,489 total
includes taxes & fees
Nov 2 - Nov 3
Sable at Navy Pier Chicago, Curio Collection by Hilton
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very Good, (4036)
"We definitely will stay there again place was very nice "
The price is ₩246,315
₩289,150 total
includes taxes & fees
Oct 20 - Oct 21
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (2419)
"Great walkable location to all the sights! "
The price is ₩134,185
₩182,288 total
includes taxes & fees
Nov 4 - Nov 5
Freehand Chicago
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (9320)
"Beautiful hotel!"
The price is ₩179,440
₩210,644 total
includes taxes & fees
Nov 2 - Nov 3
Congress Plaza Hotel
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3911)
"Great place to stay. "
The price is ₩243,884
₩286,296 total
includes taxes & fees
Nov 3 - Nov 4
citizenM Chicago Downtown
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (3027)
"Hotel was excellent!"
The price is ₩204,428
₩239,979 total
includes taxes & fees
Nov 3 - Nov 4
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very Good, (2244)
"We loved this hotel it was beautiful and convenient . "
The price is ₩258,693
₩344,962 total
includes taxes & fees
Oct 23 - Oct 24
Hilton Chicago
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1019)
"Great stay"
The price is ₩178,140
₩209,117 total
includes taxes & fees
Nov 2 - Nov 3
Best Western River North Hotel
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very Good, (264)
"Loved this place if you want something affordable and nice! "
The price is ₩137,096
₩160,937 total
includes taxes & fees
Nov 4 - Nov 5
FOUND Hotel Chicago River North
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2542)
"Location is great and the breakfast buffet is amazing"
The price is ₩225,643
₩304,519 total
includes taxes & fees
Nov 3 - Nov 4
Hotel Riu Plaza Chicago
Crowne Plaza Chicago West Loop by IHG
American cuisine

Crowne Plaza Chicago West Loop by IHG

3.5 star property
9.0 out of 10, Wonderful, (1578)
"Excellent breakfast and room was quiet and clean. "
The price is ₩212,389
₩249,324 total
includes taxes & fees
Nov 2 - Nov 3
Crowne Plaza Chicago West Loop by IHG
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, (2567)
"Good place to stay"
The price is ₩223,149
₩286,723 total
includes taxes & fees
Nov 2 - Nov 3
La Quinta Inn & Suites by Wyndham Chicago Downtown
Hyatt Centric The Loop Chicago
Rooftop terrace

Hyatt Centric The Loop Chicago

4.0 star property
9.0 out of 10, Wonderful, (2164)
"It was an amazing stay!"
The price is ₩290,692
₩341,243 total
includes taxes & fees
Nov 6 - Nov 7
Hyatt Centric The Loop Chicago
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2385)
"Comfortable bed, bright room, good shower, very accessible location."
The price is ₩151,837
₩178,252 total
includes taxes & fees
Nov 4 - Nov 5
Travelodge by Wyndham Downtown Chicago
Silversmith Hotel Chicago Downtown
Lobby

Silversmith Hotel Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (1998)
"Excellent hotel, staff, location. "
The price is ₩181,846
₩254,737 total
includes taxes & fees
Nov 2 - Nov 3
Silversmith Hotel Chicago Downtown
Palmer House a Hilton Hotel
Ballroom

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very Good, (1999)
"Great place to stay."
The price is ₩243,896
₩321,474 total
includes taxes & fees
Oct 30 - Oct 31
Palmer House a Hilton 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

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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Spotless room. Shops nearby"
David 1-night trip
Posted 15 hours ago
Congress Plaza Hotel

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 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.