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.

Top Oakland Hotels

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Our top choices for Oakland hotels

A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.

1. Hilton Vacation Club Hotel Blake Chicago

The Loop, 6.1 km from Oakland

Mario

￥32,297 total

includes taxes & fees

Nov 4 - Nov 5

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

2. LondonHouse Chicago, Curio Collection by Hilton

The Loop, 7.4 km from Oakland

Keeven

￥47,035 total

includes taxes & fees

Nov 15 - Nov 16

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

3. Hotel Riu Plaza Chicago

Streeterville, 7.9 km from Oakland

Kevin

￥33,979 total

includes taxes & fees

Nov 11 - Nov 12

A spacious bar area with high ceilings and large windows, offering views of a cityscape.

4. Hyatt Regency Chicago

The Loop, 7.3 km from Oakland

Addison

￥50,368 total

includes taxes & fees

Oct 31 - Nov 1

A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

5. Hilton Chicago

The Loop, 5.7 km from Oakland

Anna

￥35,855 total

includes taxes & fees

Oct 30 - Oct 31

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

6. L7 Chicago by LOTTE

Theatre District, 7.2 km from Oakland

Jeffrey Thomas

￥36,079 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

7. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

Aran

￥23,802 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with a large window, a dining area, and a view of the sea.

8. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

Cynthia

￥26,998 total

includes taxes & fees

Nov 10 - Nov 11

A room with two chairs and a small table, a large window with a city view at night.

9. Eurostars Magnificent Mile

River North, 8.1 km from Oakland

Will

￥27,063 total

includes taxes & fees

Nov 1 - Nov 2

A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

10. Hyatt Place Chicago/River North

River North, 7.8 km from Oakland

Nilofar

￥32,702 total

includes taxes & fees

Nov 12 - Nov 13

The Intercontinental hotel facade with a large American flag and a floral display.

11. InterContinental Chicago Magnificent Mile by IHG

Magnificent Mile, 7.7 km from Oakland

Reginald

￥45,377 total

includes taxes & fees

Oct 31 - Nov 1

A dining table set for six with a cityscape view through large windows.

12. Swissotel - Chicago

7.2 km from Oakland

Hilary

￥55,465 total

includes taxes & fees

Oct 25 - Oct 26

A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

13. Silversmith Hotel Chicago Downtown

Theatre District, 6.7 km from Oakland

Guy

￥28,856 total

includes taxes & fees

Nov 1 - Nov 2

A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

14. Aloft by Marriott Chicago Mag Mile

Streeterville, 7.9 km from Oakland

Jonathan M

￥27,193 total

includes taxes & fees

Nov 1 - Nov 2

A dining area with a table set for four, large windows offering a cityscape view at dusk.

15. The Royal Sonesta Chicago Downtown

The Loop, 7.3 km from Oakland

Jordyn

￥36,821 total

includes taxes & fees

Nov 1 - Nov 2

A modern restaurant interior with a green wall, hanging lights, and a long dining area.

16. Hotel 505 River North

River North, 7.8 km from Oakland

Giana

￥38,702 total

includes taxes & fees

Nov 15 - Nov 16

A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

17. Embassy Suites by Hilton Chicago Downtown River North

River North, 8 km from Oakland

Eliana

￥32,413 total

includes taxes & fees

Nov 2 - Nov 3

An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

18. Palmer House a Hilton Hotel

Theatre District, 6.7 km from Oakland

Christy

￥40,484 total

includes taxes & fees

Oct 31 - Nov 1

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

19. Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 7.5 km from Oakland

Shanequa

￥42,830 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

20. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 7.8 km from Oakland

Poua

￥24,906 total

includes taxes & fees

Nov 2 - Nov 3

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Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most.

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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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A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

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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A large, historic building with a central tower and multiple windows, located near a body of water.

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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A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

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