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Our top choices for Oakland hotels

Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very Good, (2686)
"Quite area in a good location to walk to different locations."
United States
John steve
The price is ₩81,648
₩121,284 total
includes taxes & fees
Feb 2 - Feb 3
Freehand Chicago
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (3099)
"Second time to stay here, everything is great!"
United States
Wei
The price is ₩143,981
₩209,730 total
includes taxes & fees
Jan 5 - Jan 6
Hotel Riu Plaza Chicago
Reception
River Hotel

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (4890)
"Would stay there again"
United States
Zach
The price is ₩105,513
₩123,862 total
includes taxes & fees
Jan 24 - Jan 25
River Hotel
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (2313)
"Great stay!"
United States
Angela
The price is ₩146,120
₩220,719 total
includes taxes & fees
Jan 20 - Jan 21
Sable at Navy Pier Chicago, Curio Collection by Hilton
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3008)
"Great place to stay"
United States
Elisha
The price is ₩118,456
₩139,056 total
includes taxes & fees
Jan 7 - Jan 8
Aloft Chicago Mag Mile
Cocktail bar
Claridge House Chicago, Tapestry Collection by Hilton

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, (1506)
"Nice stay"
United States
Michelle
The price is ₩87,658
₩145,301 total
includes taxes & fees
Feb 1 - Feb 2
Claridge House Chicago, Tapestry Collection by Hilton
Premium bedding, down comforters, pillowtop beds, in-room safe
The Wade

The Wade

The Wade
4.5 star property
Streeterville, 7.9 km from Oakland
8.4 out of 10, Very Good, (1569)
"Easy check in and out, excellent room service and dining menu."
United States
Kevin Bradford
The price is ₩133,841
₩157,117 total
includes taxes & fees
Jan 8 - Jan 9
The Wade
Terrace/patio
DoubleTree by Hilton Chicago - Magnificent Mile

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, (2218)
"Fantastic stay! Looking forward to staying here again!!"
United States
Amber
The price is ₩123,195
₩144,618 total
includes taxes & fees
Jan 11 - Jan 12
DoubleTree by Hilton Chicago - Magnificent Mile
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 7.6 km from Oakland
8.2 out of 10, Very Good, (2802)
"Great hotel staff and location. "
United States
Jacqueline
The price is ₩127,124
₩191,631 total
includes taxes & fees
Jan 13 - Jan 14
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 8.6 km from Oakland
9.0 out of 10, Wonderful, (3662)
"Great hotel"
United States
Jeanette
The price is ₩129,117
₩151,570 total
includes taxes & fees
Jan 11 - Jan 12
Hilton Chicago/Magnificent Mile Suites
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 8.1 km from Oakland
9.0 out of 10, Wonderful, (3181)
"stunning hotel"
Canada
Yiwei
The price is ₩135,214
₩158,727 total
includes taxes & fees
Feb 2 - Feb 3
Eurostars Magnificent Mile
Lobby sitting area
Warwick Allerton - Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Magnificent Mile, 8.1 km from Oakland
8.4 out of 10, Very Good, (3019)
"Every thing is perfect, the location, safe for solo travel. "
United States
Ken
The price is ₩89,998
₩148,027 total
includes taxes & fees
Jan 11 - Jan 12
Warwick Allerton - Chicago
Lobby sitting area
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (2031)
"Great stay"
United States
Kramer
The price is ₩117,879
₩138,378 total
includes taxes & fees
Jan 16 - Jan 17
Club Quarters Hotel Wacker at Michigan, Chicago
American cuisine, alfresco dining
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
River North, 8.3 km from Oakland
8.6 out of 10, Excellent, (1971)
"The room was nice, the area was perfect for walking distance for food and activities. "
United States
Alexis
The price is ₩125,968
₩181,792 total
includes taxes & fees
Feb 1 - Feb 2
The Godfrey Hotel Chicago
Property amenity
citizenM Chicago Downtown

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 7.3 km from Oakland
9.4 out of 10, Exceptional, (4146)
"Great hotel"
United States
Richard
The price is ₩146,120
₩171,530 total
includes taxes & fees
Jan 8 - Jan 9
citizenM Chicago Downtown
Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 8.6 km from Oakland
8.2 out of 10, Very Good, (3846)
" Breakfast is good, location is excellent, service staff is courteous."
United States
Luis
The price is ₩110,581
₩129,813 total
includes taxes & fees
Jan 5 - Jan 6
The Whitehall Hotel, BW Premier Collection
Exterior
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3219)
"Excellent location and the hotel is amazing I will definitely recommend "
United States
Diana Sofia Cruz
The price is ₩171,906
₩248,028 total
includes taxes & fees
Feb 1 - Feb 2
The Royal Sonesta Chicago Downtown
Rooftop terrace
Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Theatre District, 6.7 km from Oakland
9.0 out of 10, Wonderful, (2340)
"Great hotel!!"
United States
Juancarlos
The price is ₩142,682
₩203,612 total
includes taxes & fees
Jan 9 - Jan 10
Hyatt Centric The Loop Chicago
Bar (on property)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
River North, 7.8 km from Oakland
8.6 out of 10, Excellent, (4311)
"Amazing staff and perfect location "
United States
Brandi
The price is ₩112,534
₩132,104 total
includes taxes & fees
Jan 11 - Jan 12
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Breakfast, lunch and dinner served
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 6.6 km from Oakland
8.8 out of 10, Excellent, (3355)
"Great hotel "
United States
Anthony
The price is ₩117,793
₩138,277 total
includes taxes & fees
Jan 16 - Jan 17
Club Quarters Hotel, Central Loop, Chicago
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 showing rides

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

Top Oakland Hotel Reviews

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 7 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.