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Our top choices for Oakland hotels

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, (2,238 reviews)
"Great hotel "
United States
Jeffrey
The price is ¥13,477
¥15,821 total
includes taxes & fees
Feb 1 - Feb 2
DoubleTree by Hilton Chicago - Magnificent 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, (3,045 reviews)
"All around a nice stay for the holiday "
United States
Alec
The price is ¥12,168
¥14,285 total
includes taxes & fees
Jan 19 - Jan 20
Aloft Chicago Mag Mile

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (4,913 reviews)
"Would stay there again"
United States
Zach
The price is ¥12,895
¥15,136 total
includes taxes & fees
Jan 26 - Jan 27
River Hotel

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very Good, (9,766 reviews)
"Wonderful stay!"
United States
Zach
The price is ¥13,108
¥15,387 total
includes taxes & fees
Jan 14 - Jan 15
Congress Plaza Hotel

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, (3,365 reviews)
"Perfect with a pub next door!"
United States
Chad
The price is ¥12,886
¥15,125 total
includes taxes & fees
Jan 26 - Jan 27
Club Quarters Hotel, Central Loop, Chicago

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Streeterville, 8 km from Oakland
9.0 out of 10, Wonderful, (1,069 reviews)
"Amazing location, excellent service and great pool and hot tub. "
United States
Tim
The price is ¥15,487
¥22,816 total
includes taxes & fees
Jan 25 - Jan 26
Hyatt Centric Chicago 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, (3,184 reviews)
"Hospitality over all was top tier! Will definitely stay again "
United States
Margie
The price is ¥14,778
¥17,348 total
includes taxes & fees
Feb 11 - Feb 12
Eurostars Magnificent Mile

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
River North, 7.7 km from Oakland
8.8 out of 10, Excellent, (3,594 reviews)
"Great location and breakfast.. can be a bit pricey but worth it. "
Canada
Shaurya
The price is ¥19,736
¥23,168 total
includes taxes & fees
Jan 18 - Jan 19
voco Chicago Downtown - Riverwalk by IHG

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, (4,318 reviews)
"Amazing staff and perfect location "
United States
Brandi
The price is ¥12,300
¥14,438 total
includes taxes & fees
Jan 20 - Jan 21
Hilton Garden Inn Chicago Downtown/Magnificent Mile

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 7.3 km from Oakland
9.4 out of 10, Exceptional, (4,189 reviews)
"Stay was great and in a great location!! "
United States
Ashley
The price is ¥16,277
¥19,110 total
includes taxes & fees
Jan 29 - Jan 30
citizenM Chicago Downtown

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, (2,323 reviews)
"Excellent location, service, view and food!!"
United States
Christine
The price is ¥15,985
¥24,147 total
includes taxes & fees
Jan 20 - Jan 21
Sable at Navy Pier Chicago, Curio Collection by Hilton

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 7.1 km from Oakland
9.4 out of 10, Exceptional, (1,938 reviews)
"Clean and comfy room, friendly staff, great location. "
United States
Agata
The price is ¥14,105
¥21,274 total
includes taxes & fees
Jan 22 - Jan 23
Arlo 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, (2,061 reviews)
"Great stay"
United States
Kramer
The price is ¥12,895
¥15,136 total
includes taxes & fees
Jan 26 - Jan 27
Club Quarters Hotel Wacker at Michigan, Chicago

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
7.1 km from Oakland
8.6 out of 10, Excellent, (1,823 reviews)
"Great hotel"
United States
Yavuz
The price is ¥22,112
¥30,065 total
includes taxes & fees
Feb 1 - Feb 2
Radisson Blu Aqua Hotel Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 8.1 km from Oakland
8.6 out of 10, Excellent, (3,029 reviews)
"Location was perfect, easily accessible"
United States
Adarsh
The price is ¥9,134
¥15,362 total
includes taxes & fees
Jan 24 - Jan 25
Warwick Allerton - Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,436 reviews)
"The Hotel was amazing great location "
United States
Donnisha
The price is ¥24,179
¥33,021 total
includes taxes & fees
Jan 26 - Jan 27
Hyatt Regency Chicago

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Streeterville, 7.9 km from Oakland
8.4 out of 10, Very Good, (1,806 reviews)
"Very clean and comfortable hotel!"
United States
HYUNJI
Hotel Saint Clair- Magnificent Mile

The Wade

The Wade
4.5 star property
Streeterville, 7.9 km from Oakland
8.4 out of 10, Very Good, (1,598 reviews)
"Easy check in and out, excellent room service and dining menu."
United States
Kevin Bradford
The price is ¥15,961
¥18,737 total
includes taxes & fees
Feb 8 - Feb 9
The Wade

Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
3.0 star property
The Loop, 6.6 km from Oakland
9.2 out of 10, Wonderful, (1,282 reviews)
"Great environment and staff was great! Will stay here again!"
United States
Brianna
The price is ¥17,753
¥20,840 total
includes taxes & fees
Jan 29 - Jan 30
Hilton Garden Inn Chicago Central Loop

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 6.6 km from Oakland
8.6 out of 10, Excellent, (1,988 reviews)
"Clean rooms, very friendly staff, and great location"
United States
Dipayan
The price is ¥12,886
¥15,125 total
includes taxes & fees
Jan 26 - Jan 27
Central Loop 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.

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.

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.

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.

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