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Our top choices for Oakland hotels

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

1. 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, (1,222 reviews)
"Great location from both airports. Lovely hotel clean and convenient"
United Kingdom
Kanokkan
The price is 2.841.378 ₫
3.377.998 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Hilton Vacation Club Hotel Blake Chicago
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

2. 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, (3,904 reviews)
"Great Location"
United States
Natasha
The price is 3.667.241 ₫
5.119.211 ₫ total
includes taxes & fees
23 Nov - 24 Nov
LondonHouse Chicago, Curio Collection by Hilton
A dining table set for six with a cityscape view through large windows.

3. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,585 reviews)
"Great hotel"
United States
Daniel Michael
The price is 3.314.941 ₫
4.842.886 ₫ total
includes taxes & fees
26 Nov - 27 Nov
Swissotel - Chicago
A modern restaurant interior with a green wall, hanging lights, and a long dining area.

4. 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, (3,017 reviews)
"Great location, reasonably rates and a staff that made us feel like we were home from the minute we pulled up to the front of the hotel."
United States
Melvin
The price is 3.548.531 ₫
5.036.616 ₫ total
includes taxes & fees
9 Dec - 10 Dec
Hotel 505 River North
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, (3,428 reviews)
"Excellent location, lots of shops and restaurants nearby and walking distance to many sights."
Canada
Faye
The price is 4.748.394 ₫
6.538.882 ₫ total
includes taxes & fees
10 Dec - 11 Dec
InterContinental Chicago Magnificent Mile by IHG
A room with two chairs and a small table, a large window with a city view at night.

6. Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 8.1 km from Oakland
9.0 out of 10, Wonderful, (4,004 reviews)
"Everything really nice rooms and the view was amazing !!"
United States
David
The price is 3.676.636 ₫
4.371.150 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Eurostars Magnificent Mile
A spacious bar area with high ceilings and large windows, offering views of a cityscape.

7. Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,508 reviews)
"Wonderful will stay again"
United States
Kristee
The price is 3.962.101 ₫
5.621.161 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Hyatt Regency Chicago
The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

8. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (5,677 reviews)
"All the stay was perfect, location is near to all the best places"
Mexico
JESUS VERA
The price is 3.368.352 ₫
4.732.212 ₫ total
includes taxes & fees
23 Nov - 24 Nov
Hotel Riu Plaza Chicago
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.

9. L7 CHICAGO by LOTTE HOTELS

L7 CHICAGO by LOTTE HOTELS
4.5 star property
Theatre District, 7.2 km from Oakland
9.6 out of 10, Exceptional, (5,221 reviews)
"Amazing hotel will stay again"
United States
Matthew
The price is 3.701.450 ₫
4.400.654 ₫ total
includes taxes & fees
24 Nov - 25 Nov
L7 CHICAGO by LOTTE HOTELS
A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

10. 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, (1,914 reviews)
"Great location, clean hotel and overall a great place to stay."
United States
Pamela
The price is 3.216.654 ₫
3.824.280 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Hyatt Place Chicago/River North
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, (2,342 reviews)
"Loved my stay"
Canada
Joel
The price is 5.080.271 ₫
6.951.036 ₫ total
includes taxes & fees
24 Nov - 25 Nov
Fairmont Chicago at Millennium Park
A cityscape at dusk with high-rise buildings, including a Hilton hotel.

12. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 8.6 km from Oakland
9.0 out of 10, Wonderful, (5,063 reviews)
"Great place to stay"
United States
Melissa
The price is 2.589.238 ₫
3.078.346 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Hilton Chicago/Magnificent Mile Suites
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

13. 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, (2,200 reviews)
"Great place to stay at"
United States
Aran
The price is 2.466.101 ₫
2.931.948 ₫ total
includes taxes & fees
9 Dec - 10 Dec
Hilton Garden Inn Chicago Downtown South Loop
A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

14. River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,614 reviews)
"The hotel was in a great location."
United States
Shelby
The price is 2.706.074 ₫
3.217.251 ₫ total
includes taxes & fees
10 Dec - 11 Dec
River Hotel
A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

15. 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, (5,976 reviews)
"Amazing stay!"
United States
Elyjah James
The price is 2.799.255 ₫
3.328.035 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Embassy Suites by Hilton Chicago Downtown River North
A dining area with a table set for four, large windows offering a cityscape view at dusk.

16. 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, (3,692 reviews)
"Excellent hotel"
Canada
Frédéric
The price is 3.420.886 ₫
4.884.018 ₫ total
includes taxes & fees
23 Nov - 24 Nov
The Royal Sonesta Chicago Downtown
A modern rooftop lounge with white seating, a glass ceiling, and city views.

17. 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, (2,606 reviews)
"Had a great stay , view was beautiful and bed was super comfortable."
United States
Tamiya
The price is 2.130.140 ₫
3.106.414 ₫ total
includes taxes & fees
7 Dec - 8 Dec
The Godfrey Hotel Chicago
A hotel room with a large window offering a city view, a bed, a desk, and a chair.

18. Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Streeterville, 7.9 km from Oakland
9.0 out of 10, Wonderful, (2,089 reviews)
"Great location Staff was terrific"
United States
Richard
The price is 2.812.019 ₫
3.343.208 ₫ total
includes taxes & fees
6 Dec - 7 Dec
Courtyard by Marriott Chicago Magnificent Mile
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

19. 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, (2,589 reviews)
"Great location and beautiful hotel!"
United States
Jodi
The price is 2.480.446 ₫
2.949.001 ₫ total
includes taxes & fees
7 Dec - 8 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
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.

20. 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, (3,318 reviews)
"Great location . Would definitely come back there"
United States
Kevin
The price is 2.885.543 ₫
3.430.622 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Aloft by Marriott Chicago Mag Mile
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.
View all properties

Compare popular hotels in Oakland

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4
Exceptional
2,782 reviews
View
A multi-story building with a prominent entrance featuring a large archway and a sign.
Hilton Chicago
4.0 star property
8.6
Excellent
3,532 reviews
View
A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.
Le Méridien Essex Chicago
4.0 star property
9.0
Wonderful
1,000 reviews
View
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
8.8
Excellent
2,200 reviews
View
A modern kitchen with a large window, a dining area, and a view of the sea.
Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
8.8
Excellent
2,537 reviews
View

Hotels recommended for families in Oakland

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,222)
The price is 2.841.378 ₫
3.377.998 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Hilton Vacation Club Hotel Blake Chicago

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

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

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

The Loop

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

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

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

Top Oakland Hotel Reviews

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.
Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago

10/10 Excellent

Great location from both airports. Lovely hotel clean and convenient
United Kingdom
Kanokkan
Reviewed October 31, 2026
Hilton Vacation Club Hotel Blake 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.

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