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Check prices for these dates

Tonight
Feb 18 - Feb 19
Tomorrow
Feb 19 - Feb 20
This weekend
Feb 20 - Feb 22
Next weekend
Feb 27 - Mar 1

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Our top choices for Oakland hotels

Restaurant

Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 5.4 km from Oakland
8.2 out of 10, Very Good, (2,676 reviews)
"Clean room and the staff are great. "
United States
Doug
The price is ￥10,901
￥12,798 total
includes taxes & fees
Mar 1 - Mar 2
Best Western Grant Park Hotel
Interior

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very Good, (2,764 reviews)
"I enjoyed my stay"
United States
Emily
The price is ￥8,763
￥12,983 total
includes taxes & fees
Feb 22 - Feb 23
Freehand Chicago
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very Good, (9,906 reviews)
"Great location, beautiful historic hotel with clean, updated rooms. "
United States
Jennifer
The price is ￥13,664
￥16,040 total
includes taxes & fees
Feb 19 - Feb 20
Congress Plaza Hotel
Property amenity

The Wade

The Wade
4.5 star property
Streeterville, 7.9 km from Oakland
8.4 out of 10, Very Good, (1,682 reviews)
"Lovely room, beautiful hotel, wonderful staff, ideal location to navy pier & Michigan Ave. "
United States
Norah
The price is ￥13,626
￥15,996 total
includes taxes & fees
Feb 22 - Feb 23
The Wade
Pool

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 5.4 km from Oakland
8.8 out of 10, Excellent, (1,861 reviews)
"Absolutely enjoyed my time here"
United States
Quayshaun
The price is ￥13,056
￥15,327 total
includes taxes & fees
Feb 26 - Feb 27
Hilton Garden Inn Chicago Downtown South Loop
Bar (on property)

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 8.6 km from Oakland
8.4 out of 10, Very Good, (3,960 reviews)
"Great location, the room was nice and the breakfast was good. Overall great value for this property"
United States
Jorge
The price is ￥11,268
￥13,225 total
includes taxes & fees
Feb 22 - Feb 23
The Whitehall Hotel, BW Premier Collection
Shared kitchen

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
River North, 8.1 km from Oakland
8.4 out of 10, Very Good, (461 reviews)
"Amazing staff and very clean, modern rooms!"
United States
genevieve
The price is ￥9,687
￥11,371 total
includes taxes & fees
Mar 1 - Mar 2
FOUND Hotel Chicago River North
Lobby

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,081 reviews)
"Great location and friendly staff. "
United States
Pablo
The price is ￥15,157
￥17,792 total
includes taxes & fees
Feb 22 - Feb 23
Aloft Chicago Mag Mile
Terrace/patio

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 7.8 km from Oakland
8.8 out of 10, Excellent, (2,314 reviews)
"Great staff, room spotless, great price."
United States
Robert
The price is ￥14,939
￥17,535 total
includes taxes & fees
Feb 26 - Feb 27
DoubleTree by Hilton Chicago - Magnificent Mile
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, (2,377 reviews)
"Great stay"
United States
Blake
The price is ￥20,283
￥29,023 total
includes taxes & fees
Feb 22 - Feb 23
Sable at Navy Pier Chicago, Curio Collection by Hilton
Lobby

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,012 reviews)
"Great stay, good location, accommodating staff."
United States
Ian
The price is ￥14,228
￥16,703 total
includes taxes & fees
Feb 22 - Feb 23
River Hotel
Exterior

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 8.1 km from Oakland
8.6 out of 10, Excellent, (3,039 reviews)
"Great place"
United States
Omar
The price is ￥11,061
￥17,478 total
includes taxes & fees
Feb 24 - Feb 25
Warwick Allerton - Chicago
Bar (on property)

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (1,125 reviews)
"I always stay here when in town. "
United States
Jeffrey
Ivy Boutique Hotel
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, (3,365 reviews)
"Amazing place, breakfast is great , location is great - honestly great hotel! "
United States
Brisa
The price is ￥15,165
￥22,114 total
includes taxes & fees
Mar 4 - Mar 5
Hotel Riu Plaza Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 5.9 km from Oakland
7.4 out of 10, Good, (2,515 reviews)
"Always a good stay"
Canada
Domenic
The price is ￥11,636
￥13,659 total
includes taxes & fees
Feb 22 - Feb 23
Travelodge by Wyndham Downtown Chicago
Exterior

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Gold Coast, 9.3 km from Oakland
9.0 out of 10, Wonderful, (1,524 reviews)
"Great location, friendly staff and nice room"
United States
Srinivasa
The price is ￥9,719
￥15,903 total
includes taxes & fees
Feb 22 - Feb 23
Claridge House Chicago, Tapestry Collection by Hilton
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, (1,282 reviews)
"Great hotel with great location. Would definitely stay here again. "
United States
Sheila
The price is ￥14,566
￥17,098 total
includes taxes & fees
Feb 22 - Feb 23
The Chicago Hotel Collection Ambassador Gold Coast
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,202 reviews)
"Place is always top notch..stay here anytime we stay in Chicago."
United States
Jon
The price is ￥18,622
￥27,251 total
includes taxes & fees
Feb 22 - Feb 23
Swissotel - Chicago
Exterior

Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile
2.5 star property
Streeterville, 8.1 km from Oakland
8.0 out of 10, Very Good, (1,406 reviews)
"Great hotel,, like so much"
United States
Ilham
The price is ￥13,684
￥16,065 total
includes taxes & fees
Feb 22 - Feb 23
Hampton Inn Chicago Downtown/Magnificent Mile
Exterior

ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
River North, 7.9 km from Oakland
9.0 out of 10, Wonderful, (1,961 reviews)
"Very convenient place to stay friendly and helpful staff."
United States
Rick
The price is ￥12,429
￥14,591 total
includes taxes & fees
Feb 24 - Feb 25
ACME Hotel Chicago, Outset Collection by Hilton
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.

Water Tower Place

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.

Underground passage in the Chicago O'Hare airport

O'Hare

Home to O'Hare International Airport, this transportation hub offers easy access to downtown via the Blue Line. The area also hosts various corporate headquarters and international consulates.

Top Oakland Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Yes but hot"
Melissa 3-night trip
Posted 9 hours ago
Hyatt Regency Chicago

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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