Find hotels in Oakland, Chicago from ￥21,378

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Discover 4,469 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
8.8 out of 10, Excellent, (3078)
"Perfect location, walkable to many restaurants and shops"
The price is ￥26,103
￥30,644 total
includes taxes & fees
Oct 27 - Oct 28
Eurostars Magnificent Mile
River Hotel
Reception

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4720)
"Excellent friendly, staff, very clean, comfy beds!"
The price is ￥27,506
￥32,290 total
includes taxes & fees
Oct 5 - Oct 6
River Hotel
Aloft Chicago Mag Mile
Lobby

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2859)
"Had a great stay!"
The price is ￥24,068
￥28,253 total
includes taxes & fees
Oct 5 - Oct 6
Aloft Chicago Mag 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, (2081)
"Staff was very friendly, rooms were cleaned daily, and the onsite restaurant was fantastic!"
The price is ￥27,387
￥32,150 total
includes taxes & fees
Oct 19 - Oct 20
DoubleTree by Hilton Chicago - Magnificent Mile
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, (4006)
"Excellent central location and local dining options. "
The price is ￥27,964
￥32,827 total
includes taxes & fees
Oct 1 - Oct 2
Hilton Garden Inn Chicago Downtown/Magnificent Mile
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, (2174)
"Great hotel "
The price is ￥28,582
￥37,887 total
includes taxes & fees
Oct 19 - Oct 20
Sable at Navy Pier Chicago, Curio Collection by Hilton
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (2402)
"Location was excellent would stay there again"
The price is ￥15,969
￥21,378 total
includes taxes & fees
Oct 28 - Oct 29
Freehand Chicago
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (3884)
"Absolutely loved this hotel and location. "
The price is ￥33,486
￥39,309 total
includes taxes & fees
Oct 1 - Oct 2
citizenM Chicago Downtown
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (9339)
"The staff was top notch, the bed so comfortable, just a great overall stay"
The price is ￥30,171
￥35,416 total
includes taxes & fees
Sep 29 - Sep 30
Congress Plaza Hotel
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very Good, (2222)
"Great Hotel"
The price is ￥27,494
￥36,663 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, (1040)
"It was a great stay"
The price is ￥22,745
￥26,700 total
includes taxes & fees
Oct 2 - Oct 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, (259)
"Lovely hotel."
The price is ￥15,691
￥18,419 total
includes taxes & fees
Oct 1 - Oct 2
FOUND Hotel Chicago River North
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (3004)
"Enjoyed our stay"
The price is ￥24,016
￥28,194 total
includes taxes & fees
Oct 20 - Oct 21
Hilton Chicago/Magnificent Mile Suites
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2495)
"Nice hotel with amazing breakfasts and location."
The price is ￥25,401
￥34,031 total
includes taxes & fees
Oct 1 - Oct 2
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, (2564)
"Very nice stay "
The price is ￥28,254
￥35,800 total
includes taxes & fees
Oct 2 - Oct 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, (2157)
"Great place and really nice people "
The price is ￥30,895
￥36,268 total
includes taxes & fees
Oct 3 - Oct 4
Hyatt Centric The Loop Chicago
Palmer House a Hilton Hotel
Ballroom

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very Good, (1994)
"Wonderful historic property, we loved our stay in this beautiful hotel"
The price is ￥34,181
￥43,862 total
includes taxes & fees
Oct 6 - Oct 7
Palmer House a Hilton Hotel
Silversmith Hotel Chicago Downtown
Lobby

Silversmith Hotel Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (1994)
"Excellent hotel, staff, location. "
Silversmith Hotel Chicago Downtown
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2388)
"The rooms were quiet, clean, and the bed was comfortable."
The price is ￥17,535
￥20,585 total
includes taxes & fees
Oct 20 - Oct 21
Travelodge by Wyndham Downtown Chicago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.4 out of 10, Very Good, (2194)
"All the staff were amazing and very helpful with my whole stay would recommend and would love to cone back in the future. "
The price is ￥23,560
￥27,658 total
includes taxes & fees
Oct 19 - Oct 20
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
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 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

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Very nice area right by the river. "
Gurnam 4-night trip
Posted 16 hours ago
Hyatt Regency Chicago

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.