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Oakland hotels in Chicago

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Our top choices for Oakland hotels

1. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (3,003 reviews)
"Great location, friendly staff, various amenities for the family."
Canada
kun
The price is HK$1,527
HK$2,045 total
includes taxes & fees
30 Aug - 31 Aug
Hilton Chicago

2. 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, (2,623 reviews)
"Nice Stay"
United States
Morgan
The price is HK$1,613
HK$2,188 total
includes taxes & fees
31 Aug - 1 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton

3. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
The Loop, 5.4 km from Oakland
8.8 out of 10, Excellent, (2,398 reviews)
"Great stay"
United Kingdom
jayne
The price is HK$1,467
HK$1,744 total
includes taxes & fees
31 Aug - 1 Sept
Homewood Suites by Hilton Chicago Downtown South Loop

4. 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, (2,278 reviews)
"Clean room, staff was very helpful, and location was great and certainly accessible to many locations"
United States
Allan
The price is HK$2,580
HK$3,348 total
includes taxes & fees
15 Aug - 16 Aug
Fairmont Chicago at Millennium Park

5. Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop
3.0 star property
The Loop, 7.1 km from Oakland
8.8 out of 10, Excellent, (1,490 reviews)
"Enjoyed my stay!"
United States
Kimberly
The price is HK$1,545
HK$1,837 total
includes taxes & fees
30 Aug - 31 Aug
Hyatt Place Chicago/Downtown - The Loop

6. Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 5.4 km from Oakland
8.2 out of 10, Very good, (2,753 reviews)
"Good stay!"
United States
Adit
The price is HK$1,122
HK$1,334 total
includes taxes & fees
30 Aug - 31 Aug
Best Western Grant Park Hotel

7. Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
3.0 star property
The Loop, 6.6 km from Oakland
9.2 out of 10, Wonderful, (1,392 reviews)
"Very nice would stay again"
United States
Dawn
The price is HK$1,660
HK$1,974 total
includes taxes & fees
16 Aug - 17 Aug
Hilton Garden Inn Chicago Central Loop

8. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
The Loop, 6.1 km from Oakland
9.6 out of 10, Exceptional, (1,292 reviews)
"Very helpful front desk staff and friendly cleaners. Very pleasant stay"
United States
Aleace
The price is HK$1,311
HK$1,559 total
includes taxes & fees
30 Aug - 31 Aug
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

9. Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,449 reviews)
"Great hotel in great location"
United States
Emily
The price is HK$1,757
HK$2,368 total
includes taxes & fees
30 Aug - 31 Aug
Hyatt Regency Chicago

10. La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
The Loop, 7 km from Oakland
8.6 out of 10, Excellent, (2,847 reviews)
"Location is very good and staff is nice!"
United States
Diana
The price is HK$1,349
HK$1,743 total
includes taxes & fees
30 Aug - 31 Aug
La Quinta Inn & Suites by Wyndham Chicago Downtown

11. 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, (2,543 reviews)
"Loved the pool and the close proximity downtown!"
United States
Macy
The price is HK$1,260
HK$1,498 total
includes taxes & fees
30 Aug - 31 Aug
DoubleTree by Hilton Chicago - Magnificent Mile

12. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (4,879 reviews)
"We were very happy with our stay."
United States
Deanne
The price is HK$1,630
HK$2,162 total
includes taxes & fees
30 Aug - 31 Aug
Hotel Riu Plaza Chicago

13. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,166 reviews)
"Great place to stay"
United States
ERIC
The price is HK$1,235
HK$1,469 total
includes taxes & fees
30 Aug - 31 Aug
Congress Plaza Hotel

14. Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG
3.0 star property
West Loop, 6.4 km from Oakland
8.6 out of 10, Excellent, (1,113 reviews)
"good hotel"
United States
Chimere
The price is HK$1,207
HK$1,529 total
includes taxes & fees
30 Aug - 31 Aug
Holiday Inn & Suites Chicago - Downtown by IHG

15. 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, (1,884 reviews)
"Great location, good breakfast and super nice staff"
United States
Michelle
The price is HK$1,333
HK$1,585 total
includes taxes & fees
16 Aug - 17 Aug
Hyatt Place Chicago/River North

16. Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District
3.0 star property
Theatre District, 6.7 km from Oakland
9.2 out of 10, Wonderful, (1,000 reviews)
"Excellent hotel! Very clean staff very nice and respectful. Breakfast was very tasty."
United States
Naidy
The price is HK$1,473
HK$1,751 total
includes taxes & fees
16 Aug - 17 Aug
Hampton Inn Majestic Chicago Theatre District

17. 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, (2,106 reviews)
"Family friendly property close to sites."
United States
Heather
The price is HK$1,393
HK$1,657 total
includes taxes & fees
31 Aug - 1 Sept
Hilton Garden Inn Chicago Downtown South Loop

18. Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Theatre District, 6.8 km from Oakland
9.0 out of 10, Wonderful, (2,680 reviews)
"Great location"
United States
Dee
The price is HK$1,592
HK$2,089 total
includes taxes & fees
23 Aug - 24 Aug
Hyatt Centric The Loop Chicago

19. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
7.9 km from Oakland
9.0 out of 10, Wonderful, (1,312 reviews)
"Very nice hotel"
United States
Hadi
The price is HK$1,796
HK$2,135 total
includes taxes & fees
30 Aug - 31 Aug
Hyatt House Chicago/West Loop-Fulton Market

20. Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
3.5 star property
7.3 km from Oakland
9.0 out of 10, Wonderful, (2,447 reviews)
"The staff was very friendly and the rooms were amazing"
United States
Amy
The price is HK$1,613
HK$1,918 total
includes taxes & fees
20 Aug - 21 Aug
Crowne Plaza Chicago West Loop by IHG
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.

Where to stay in Oakland

Find the best Oakland areas 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.

The Loop

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

Magnificent Mile

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

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.

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 of the city at Washington Station or Monroe Station (Blue Line).

Top Oakland Hotel Reviews

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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