What's it like in Oakland?

Oakland is a neighbourhood that travellers 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 neighbourhood.

How many hotels can I expect to find in Oakland?

When you want to find places to stay in Chicago, start by booking one of Expedia's 7 hotels and other accommodation options in Oakland.

If I need to cancel my hotel reservation in Oakland, will I receive a refund?

Yes, you'll find most hotel room reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of check in. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of booking. Add your dates and click on "Search", then filter by "fully refundable" to view the top deals on offer in Oakland.

What can I see and do in this Chicago neighbourhood?

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 neighbourhood. 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 10 Oakland Hotels of 2026 | Expedia Singapore

A cityscape with modern skyscrapers, a river, and a bridge.

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Our top choices for Oakland hotels

A large, historic building with a central courtyard surrounded by trees.

1. Hilton Chicago

The Loop, 5.7 km from Oakland

Alan

includes taxes & fees

30 Oct - 31 Oct

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

2. Congress Plaza Hotel

The Loop, 6 km from Oakland

Guadalupe

includes taxes & fees

25 Oct - 26 Oct

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

3. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

Aran

includes taxes & fees

25 Oct - 26 Oct

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

4. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 5.4 km from Oakland

Cecilia

includes taxes & fees

25 Oct - 26 Oct

A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

5. Travelodge by Wyndham Downtown Chicago

The Loop, 5.9 km from Oakland

Sandra

includes taxes & fees

25 Oct - 26 Oct

A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

6. Club Quarters Hotel, Central Loop, Chicago

Theatre District, 6.6 km from Oakland

Julian

includes taxes & fees

25 Oct - 26 Oct

A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

7. Le Méridien Essex Chicago

The Loop, 5.6 km from Oakland

Kayla Rene

includes taxes & fees

30 Oct - 31 Oct

A cozy room with a sofa, a dining table, and a window with a view of buildings.

8. LIVN - West Loop Chicago

6.8 km from Oakland

chidubem

includes taxes & fees

1 Oct - 2 Oct

A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

9. The Wade

Streeterville, 7.9 km from Oakland

Erin

includes taxes & fees

25 Oct - 26 Oct

A multi-story hotel with a prominent sign reading "Crowne Plaza."

10. Crowne Plaza Chicago West Loop by IHG

7.3 km from Oakland

Phillip

includes taxes & fees

25 Oct - 26 Oct

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

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

Streeterville, 7.5 km from Oakland

Shanequa

includes taxes & fees

29 Oct - 30 Oct

A snack bar with various packaged snacks and beverages.

12. Cambria Hotel Chicago Loop - Theatre District

Theatre District, 7.1 km from Oakland

Sai Sudarshan

includes taxes & fees

25 Oct - 26 Oct

A street view with a row of parked cars, a building with a sign reading "SONDE," and another sign that says "Diamonds On Parade."

13. LIVN - Millennium Park Downtown Chicago

Theatre District, 6.7 km from Oakland

Rebecca

includes taxes & fees

1 Oct - 2 Oct

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

14. Silversmith Hotel Chicago Downtown

Theatre District, 6.7 km from Oakland

Haesung

includes taxes & fees

25 Oct - 26 Oct

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

15. Hilton Chicago/Magnificent Mile Suites

Streeterville, 8.6 km from Oakland

Alan

includes taxes & fees

25 Oct - 26 Oct

16. Central Loop Hotel

Theatre District, 6.6 km from Oakland

Nathan

includes taxes & fees

25 Oct - 26 Oct

A couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.

17. Hotel Saint Clair- Magnificent Mile

Streeterville, 7.9 km from Oakland

Adhba

includes taxes & fees

1 Oct - 2 Oct

A restaurant interior with brick walls, hanging spherical light fixtures, and a visible kitchen area.

18. Arlo Chicago

Theatre District, 7.1 km from Oakland

Ashley Nacole

includes taxes & fees

25 Oct - 26 Oct

A grand lobby with a central bar, high ceilings, and classical architecture.

19. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Theatre District, 6.7 km from Oakland

Amanda

includes taxes & fees

23 Oct - 24 Oct

20. The Allegro Royal Sonesta Hotel Chicago Loop

Theatre District, 7.2 km from Oakland

Reginald

includes taxes & fees

25 Oct - 26 Oct

View all properties

Where to stay in Oakland

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

A cityscape with tall skyscrapers and a historic tower.

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

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

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A river with yellow boats, a bridge, and tall buildings.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

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Top Oakland Hotel Reviews

L7 Chicago by LOTTE

10/10 Excellent

"Excelente"

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent

"We enjoyed our stay and first visit to Chicago. All the staff were very helpful except one young lady at desk unable to help us with questions about the L train and told us to use our phones. We are an older couple 76& 80 and would have appreciated some assistance."

Hotel Saint Clair- Magnificent Mile

8/10 Good

"The room we were assigned had a wheelchair accessible bathroom which was very large took up a considerable amount of space in the room. We could barely walk around the bed, and there were no chairs nor a small desk or table. I’m not sure why we were assigned a room designed for wheelchairs, because we didn’t request any special accommodations. I’m sure they would have moved us if we had asked, but we really didn’t spend much time in the room other than to sleep. The room and bathroom were very clean and everything was working properly. The location was outstanding. We would definitely stay there again."

River Hotel

8/10 Good

"The staff at this hotel were all very friendly and helpful. I requested extra coffee and other supplies for the room several times and they never failed to bring it to our room promptly. I did think the interior of our room was a bit outdated and could use some updating. The furniture, carpet, and bathroom all had a very old look and definitely needed updating badly. That was very minor though. Overall we enjoyed our stay very much. There were some loud motorcycles and cars every night that insisted on constantly revving their engines around 11pm-12am which was annoying. Not the fault of the property at all, but definitely something to be aware of if you’re wanting a more quiet atmosphere."

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Great location 2 blocks to Lake Michigan! Room was very nice. Bed was really comfortable except it was low to the ground like a futon. No coffee maker in room. coffee in lobby. Parking is valet and convenient but pricey 82 per day. Fir us it was worth it. Navy pier is close, LINCOLN PARK ZOO has the best gorilla exhibit ever! And zoo is free! Dont go to saquarium if it a football game day no parking so we missed out. The boat tour at Navy pier is so worth the low cost to see lake Michigan! Breakfast buffet at hotel is decent. Bar is nice. Deck on the 17th foor is wonderful."

Hotels in Oakland

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Our top choices for Oakland hotels

1. Hilton Chicago

2. Congress Plaza Hotel

3. Hilton Garden Inn Chicago Downtown South Loop

4. Homewood Suites by Hilton Chicago Downtown South Loop

5. Travelodge by Wyndham Downtown Chicago

6. Club Quarters Hotel, Central Loop, Chicago

7. Le Méridien Essex Chicago

8. LIVN - West Loop Chicago

9. The Wade

10. Crowne Plaza Chicago West Loop by IHG

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

12. Cambria Hotel Chicago Loop - Theatre District

13. LIVN - Millennium Park Downtown Chicago

14. Silversmith Hotel Chicago Downtown

15. Hilton Chicago/Magnificent Mile Suites

16. Central Loop Hotel

17. Hotel Saint Clair- Magnificent Mile

18. Arlo Chicago

19. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

20. The Allegro Royal Sonesta Hotel Chicago Loop

Where to stay in Oakland

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Oakland Hotel Reviews

L7 Chicago by LOTTE

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