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

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Check prices for these dates

Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov

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Our top choices for Oakland hotels

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

1. 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, (3,877 reviews)
"It was a very nice stay! We enjoyed the hotel The views were amazing"
United States
James
The price is Rp3.999.290
Rp5.290.880 total
includes taxes & fees
1 Nov - 2 Nov
LondonHouse Chicago, Curio Collection by Hilton
A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.

2. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 6.1 km from Oakland
9.6 out of 10, Exceptional, (1,221 reviews)
"Great location!"
United States
Mario
The price is Rp3.097.760
Rp3.683.096 total
includes taxes & fees
3 Nov - 4 Nov
Hilton Vacation Club Hotel Blake Chicago
The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

3. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (5,545 reviews)
"Excellent staff, excellent location, great resort style breakfast buffet"
United States
Scott E
The price is Rp3.336.892
Rp4.481.000 total
includes taxes & fees
11 Nov - 12 Nov
Hotel Riu Plaza Chicago
A room with two chairs and a small table, a large window with a city view at night.

4. Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 8.1 km from Oakland
9.0 out of 10, Wonderful, (3,959 reviews)
"Fantastic stay"
United States
Will
The price is Rp2.740.104
Rp3.257.708 total
includes taxes & fees
1 Nov - 2 Nov
Eurostars Magnificent Mile
The Intercontinental hotel facade with a large American flag and a floral display.

5. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Magnificent Mile, 7.7 km from Oakland
9.2 out of 10, Wonderful, (3,389 reviews)
"Great hotel"
United States
Said Lopez
The price is Rp3.821.724
Rp5.174.592 total
includes taxes & fees
31 Oct - 1 Nov
InterContinental Chicago Magnificent Mile by IHG
A modern restaurant interior with a green wall, hanging lights, and a long dining area.

6. Hotel 505 River North

Hotel 505 River North
4.5 star property
River North, 7.8 km from Oakland
9.2 out of 10, Wonderful, (2,962 reviews)
"Ideal location, excellent large rooms."
United Kingdom
Jordan
The price is Rp3.226.833
Rp4.413.473 total
includes taxes & fees
15 Nov - 16 Nov
Hotel 505 River North
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.

7. L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 7.2 km from Oakland
9.6 out of 10, Exceptional, (5,055 reviews)
"A fantastic A+ location in a well kept, boutique type hotel."
United States
Jeffrey Thomas
The price is Rp2.993.384
Rp3.558.835 total
includes taxes & fees
1 Nov - 2 Nov
L7 Chicago by LOTTE
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

8. 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, (2,195 reviews)
"Great place to stay at"
United States
Aran
The price is Rp2.666.193
Rp3.169.835 total
includes taxes & fees
12 Nov - 13 Nov
Hilton Garden Inn Chicago Downtown South Loop
A modern interior with a branded sign, a wine rack, and a table with a vase.

9. Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,515 reviews)
"The hotel was beautiful, great location"
United States
Addison
The price is Rp4.290.426
Rp5.743.910 total
includes taxes & fees
31 Oct - 1 Nov
Hyatt Regency Chicago
A dining area with a table set for four, large windows offering a cityscape view at dusk.

10. The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,658 reviews)
"Great location and friendly staff."
United States
Jordyn
The price is Rp3.046.563
Rp4.198.922 total
includes taxes & fees
1 Nov - 2 Nov
The Royal Sonesta Chicago Downtown
A modern kitchen with a marble island, fruit bowls, and a city view.

11. Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 7.1 km from Oakland
8.8 out of 10, Excellent, (2,322 reviews)
"Beautiful hotel and great location."
United States
Ruby
The price is Rp5.390.073
Rp7.051.622 total
includes taxes & fees
25 Oct - 26 Oct
Fairmont Chicago at Millennium Park
A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

12. Hyatt Place Chicago/River North

Hyatt Place Chicago/River North
3.5 star property
River North, 7.8 km from Oakland
9.2 out of 10, Wonderful, (1,920 reviews)
"Great location!"
United States
Nilofar
The price is Rp3.136.698
Rp3.729.221 total
includes taxes & fees
12 Nov - 13 Nov
Hyatt Place Chicago/River North
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

13. 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, (2,731 reviews)
"Amazing place to stay"
United States
Shanequa
The price is Rp3.401.695
Rp4.665.847 total
includes taxes & fees
12 Nov - 13 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
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

Aloft by Marriott Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,333 reviews)
"nice chic clean place to stay near navy pier"
United States
Jonathan M
The price is Rp2.608.327
Rp3.101.038 total
includes taxes & fees
1 Nov - 2 Nov
Aloft by Marriott Chicago Mag Mile
An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

15. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 6.7 km from Oakland
8.6 out of 10, Excellent, (2,713 reviews)
"Beautiful hotel with wonderful staff!"
United States
Christy
The price is Rp3.432.341
Rp4.616.652 total
includes taxes & fees
31 Oct - 1 Nov
Palmer House a Hilton Hotel
A dining table set for six with a cityscape view through large windows.

16. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,567 reviews)
"Great stay"
United States
Hilary
The price is Rp4.039.851
Rp5.437.891 total
includes taxes & fees
9 Nov - 10 Nov
Swissotel - Chicago
A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

17. Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 6.7 km from Oakland
9.2 out of 10, Wonderful, (2,433 reviews)
"Great location, great staff very pleasant stay in a historical building"
United States
Guy
The price is Rp2.606.434
Rp3.648.971 total
includes taxes & fees
1 Nov - 2 Nov
Silversmith Hotel Chicago Downtown
A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

18. Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
River North, 8 km from Oakland
8.6 out of 10, Excellent, (5,989 reviews)
"I’d stay here again."
United States
Eliana
The price is Rp2.742.808
Rp3.260.924 total
includes taxes & fees
1 Nov - 2 Nov
Embassy Suites by Hilton Chicago Downtown River North
An outdoor seating area with modern furniture and potted plants.

19. 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, (2,156 reviews)
"Loved the hotel!"
United States
Shannon
The price is Rp4.267.351
Rp5.630.669 total
includes taxes & fees
1 Nov - 2 Nov
Radisson Blu Aqua Hotel Chicago
A modern rooftop lounge with white seating, a glass ceiling, and city views.

20. The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
River North, 8.3 km from Oakland
8.8 out of 10, Excellent, (2,572 reviews)
"Incredible stay & very walkable to areas of interest"
United States
Jo
The price is Rp2.581.466
Rp3.474.350 total
includes taxes & fees
12 Nov - 13 Nov
The Godfrey Hotel 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 for the activities you enjoy most. Learn more about Oakland
Learn more about Oakland
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.

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

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.

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.

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.

Top Oakland Hotel Reviews

Freehand Chicago

Freehand Chicago

10/10 Excellent
"A great stay ! It was really quiet The room was modest. Some room damage but clean and everything worked well including the AC and shower ! Staff were really nice Location was great. I recommend this hotel"
Ryan 1-night trip
Posted less than an hour ago
Freehand Chicago

Frequently asked questions

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.