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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Dates

January 2026

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February 2026

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Our top choices for Oakland hotels

DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 7.8 km from Oakland

Jeffrey

￥15,821 total

includes taxes & fees

Feb 1 - Feb 2

Aloft Chicago Mag Mile

Streeterville, 7.9 km from Oakland

Alec

￥14,285 total

includes taxes & fees

Jan 19 - Jan 20

River Hotel

The Loop, 7.4 km from Oakland

Zach

￥15,136 total

includes taxes & fees

Jan 26 - Jan 27

Congress Plaza Hotel

The Loop, 6 km from Oakland

Zach

￥15,387 total

includes taxes & fees

Jan 14 - Jan 15

Club Quarters Hotel, Central Loop, Chicago

Theatre District, 6.6 km from Oakland

Chad

￥15,125 total

includes taxes & fees

Jan 26 - Jan 27

Hyatt Centric Chicago Magnificent Mile

Streeterville, 8 km from Oakland

Tim

￥22,816 total

includes taxes & fees

Jan 25 - Jan 26

Eurostars Magnificent Mile

River North, 8.1 km from Oakland

Margie

￥17,348 total

includes taxes & fees

Feb 11 - Feb 12

voco Chicago Downtown - Riverwalk by IHG

River North, 7.7 km from Oakland

Shaurya

￥23,168 total

includes taxes & fees

Jan 18 - Jan 19

Hilton Garden Inn Chicago Downtown/Magnificent Mile

River North, 7.8 km from Oakland

Brandi

￥14,438 total

includes taxes & fees

Jan 20 - Jan 21

citizenM Chicago Downtown

Theatre District, 7.3 km from Oakland

Ashley

￥19,110 total

includes taxes & fees

Jan 29 - Jan 30

Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 7.5 km from Oakland

Christine

￥24,147 total

includes taxes & fees

Jan 20 - Jan 21

Arlo Chicago

Theatre District, 7.1 km from Oakland

Agata

￥21,274 total

includes taxes & fees

Jan 22 - Jan 23

Club Quarters Hotel Wacker at Michigan, Chicago

The Loop, 7.4 km from Oakland

Kramer

￥15,136 total

includes taxes & fees

Jan 26 - Jan 27

Radisson Blu Aqua Hotel Chicago

7.1 km from Oakland

Yavuz

￥30,065 total

includes taxes & fees

Feb 1 - Feb 2

Warwick Allerton - Chicago

Streeterville, 8.1 km from Oakland

Adarsh

￥15,362 total

includes taxes & fees

Jan 24 - Jan 25

Hyatt Regency Chicago

The Loop, 7.3 km from Oakland

Donnisha

￥33,021 total

includes taxes & fees

Jan 26 - Jan 27

Hotel Saint Clair- Magnificent Mile

Streeterville, 7.9 km from Oakland

HYUNJI

The Wade

Streeterville, 7.9 km from Oakland

Kevin Bradford

￥18,737 total

includes taxes & fees

Feb 8 - Feb 9

Hilton Garden Inn Chicago Central Loop

The Loop, 6.6 km from Oakland

Brianna

￥20,840 total

includes taxes & fees

Jan 29 - Jan 30

Central Loop Hotel

Theatre District, 6.6 km from Oakland

Dipayan

￥15,125 total

includes taxes & fees

Jan 26 - Jan 27

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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.

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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.

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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.

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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.

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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).

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Top Oakland Hotel Reviews

River Hotel

10/10 Excellent

"Our stay was A+, the staff was courteous and helpful and always went above and beyond in service. The location was great across from the Riverwalk and central to many other Chicago attractions. We will be back!!"