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Check prices for these dates

Tonight
Apr 14 - Apr 15
Tomorrow
Apr 15 - Apr 16
This weekend
Apr 17 - Apr 19
Next weekend
Apr 24 - Apr 26

Our top choices for Oakland hotels

Cocktail bar

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very Good, (2,872 reviews)
"Great location, clean and decent sized room, staff was helpful and amenities are very convenient!"
United States
MaryJane
The price is ￥11,773
￥16,619 total
includes taxes & fees
Apr 27 - Apr 28
Freehand Chicago
Lobby

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,092 reviews)
"Great location and nice hotel! "
United States
James
The price is ￥16,606
￥19,494 total
includes taxes & fees
Apr 28 - Apr 29
River Hotel
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, (1,365 reviews)
"The staff is so amazing, and accommodating, Cristin and David are amazing when helping! The area is so fun and so close to so many shopping centers and great places to eat. In a very convenient spot for traveling in !! "
United States
Sonovia
The price is ￥17,680
￥20,756 total
includes taxes & fees
Apr 28 - Apr 29
The Chicago Hotel Collection Ambassador Gold Coast
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, (3,182 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is ￥20,490
￥24,058 total
includes taxes & fees
Apr 19 - Apr 20
Aloft Chicago Mag Mile
Lobby

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
River North, 8.1 km from Oakland
8.6 out of 10, Excellent, (547 reviews)
"Love this place. Kind of like a college dorm with community kitchen. Will stay there again. "
United States
William
The price is ￥12,141
￥14,253 total
includes taxes & fees
Apr 27 - Apr 28
FOUND Hotel Chicago River North
2 restaurants, breakfast, lunch, dinner served; American cuisine

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 7.4 km from Oakland
9.4 out of 10, Exceptional, (3,642 reviews)
"Great location"
United States
Margaret
The price is ￥37,138
￥48,819 total
includes taxes & fees
May 7 - May 8
LondonHouse Chicago, Curio Collection by Hilton
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very Good, (10,147 reviews)
"Clean room, nice hotel, nice staff"
United States
Melanie
The price is ￥19,650
￥23,068 total
includes taxes & fees
Apr 26 - Apr 27
Congress Plaza 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, (3,836 reviews)
"The property was absolutely stunning and the staff was great."
United States
Pamela
The price is ￥19,853
￥27,783 total
includes taxes & fees
Apr 19 - Apr 20
Hotel Riu Plaza Chicago
Exterior

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 8.1 km from Oakland
8.6 out of 10, Excellent, (3,045 reviews)
"Excellent service, clean, comfortable, and a great location. "
United States
Lisa
The price is ￥16,933
￥24,558 total
includes taxes & fees
Apr 26 - Apr 27
Warwick Allerton - Chicago
Lobby

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Streeterville, 7.9 km from Oakland
9.0 out of 10, Wonderful, (1,017 reviews)
"Rooms were very clean and the staff were all very professional."
United States
Mitchell
The price is ￥18,441
￥21,649 total
includes taxes & fees
Apr 28 - Apr 29
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
2 bars/lounges

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,502 reviews)
"Increíble hotel súper friendly staff! "
United States
Alejandra
The price is ￥39,551
￥52,617 total
includes taxes & fees
May 9 - May 10
Hyatt Regency Chicago
Lobby sitting area

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, (2,189 reviews)
"Great room, lovely staff and fantastic location "
United Kingdom
Jessica
The price is ￥19,537
￥22,937 total
includes taxes & fees
Apr 28 - Apr 29
Club Quarters Hotel Wacker at Michigan, Chicago
Nightclub

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, (3,460 reviews)
"Wonderful hotel, friendly and accommodating staff! "
United States
Chevon
The price is ￥18,362
￥21,556 total
includes taxes & fees
Apr 28 - Apr 29
Club Quarters Hotel, Central Loop, Chicago
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, (1,954 reviews)
"The staff here were extremely friendly and made the stay more enjoyable "
United States
Trinity
The price is ￥18,756
￥22,018 total
includes taxes & fees
Apr 28 - Apr 29
Hilton Garden Inn Chicago Downtown South Loop
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, (1,520 reviews)
"Very nice hotel, great location. Will stay again!"
United States
Monica
The price is ￥14,197
￥21,329 total
includes taxes & fees
Apr 28 - Apr 29
Claridge House Chicago, Tapestry Collection by Hilton
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, (2,464 reviews)
"Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. "
United States
Christopher
The price is ￥35,216
￥46,770 total
includes taxes & fees
Apr 26 - Apr 27
Sable at Navy Pier Chicago, Curio Collection by Hilton
Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Millennium Hotel Knickerbocker Chicago

Millennium Hotel Knickerbocker Chicago
4.0 star property
Streeterville, 8.6 km from Oakland
8.6 out of 10, Excellent, (1,962 reviews)
"Great location, clean hotel"
United States
Andre
The price is ￥17,212
￥23,948 total
includes taxes & fees
Apr 19 - Apr 20
Millennium Hotel Knickerbocker Chicago
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, (2,422 reviews)
"Perfect location, beautiful clean rooms and friendly staff "
United Kingdom
Maureen
The price is ￥23,235
￥27,277 total
includes taxes & fees
Apr 26 - Apr 27
DoubleTree by Hilton Chicago - Magnificent Mile
Cocktail bar

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, (1,998 reviews)
"Excellent location for shops,restaurants and casino."
United States
Deborah
The price is ￥18,114
￥21,265 total
includes taxes & fees
Apr 28 - Apr 29
ACME Hotel Chicago, Outset Collection by Hilton
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,266 reviews)
"Great connecting room and always an amazing stay I always come for the atmosphere and great staff!"
United States
Kavita
The price is ￥34,182
￥46,234 total
includes taxes & fees
May 9 - May 10
Swissotel - 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.

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

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.

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.

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

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.

Top Oakland Hotel Reviews

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"It’s all good but they didn’t allow me to take just a cup of coffee to my room and that I did not like at all. After seeing the tiktok where girls washes underwear in hotel room coffee machine I will never make coffee in hotels rooms ever and that’s why I wanted to enjoy the morning coffee from dining hall but wasn’t allowed therefore my rating is F "
Shah 2-night trip
Posted 1 hour ago
Hotel Riu Plaza 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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