Oakland hotels in Chicago

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Our top choices for Oakland hotels

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, (2,449 reviews)
"Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. "
United States
Christopher
The price is HK$1,795
HK$2,373 total
includes taxes & fees
16 Apr - 17 Apr
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (2,372 reviews)
"Beautiful property, great resturant on site, an the pool and spa was amazing."
United States
Tim
The price is HK$1,310
HK$1,734 total
includes taxes & fees
10 May - 11 May
Palmer House a Hilton Hotel

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,488 reviews)
"Increíble hotel súper friendly staff! "
United States
Alejandra
The price is HK$1,912
HK$2,520 total
includes taxes & fees
9 May - 10 May
Hyatt Regency Chicago

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 9.4 km from Oakland
8.2 out of 10, Very good, (1,359 reviews)
"Very beautiful place to stay"
United States
angie
The price is HK$891
HK$1,046 total
includes taxes & fees
26 Apr - 27 Apr
The Chicago Hotel Collection Ambassador Gold Coast

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,066 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is HK$909
HK$1,067 total
includes taxes & fees
12 Apr - 13 Apr
River Hotel

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,076 reviews)
"The stay is well worth the affordable price."
United States
Thomas
The price is HK$901
HK$1,058 total
includes taxes & fees
26 Apr - 27 Apr
Congress Plaza Hotel

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, (2,107 reviews)
"lovely hotel "
United States
alyvia
The price is HK$1,951
HK$2,566 total
includes taxes & fees
25 Apr - 26 Apr
Fairmont Chicago at Millennium Park

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, (2,236 reviews)
"Great stay!"
United States
Jessica
The price is HK$953
HK$1,357 total
includes taxes & fees
26 Apr - 27 Apr
Silversmith Hotel Chicago Downtown

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, (1,906 reviews)
"Overall a great stay."
United States
Joshua
The price is HK$1,717
HK$2,219 total
includes taxes & fees
9 May - 10 May
Radisson Blu Aqua Hotel Chicago

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,164 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is HK$1,011
HK$1,186 total
includes taxes & fees
26 Apr - 27 Apr
Aloft Chicago Mag Mile

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, (3,367 reviews)
"I loved my stay"
United States
Janet
The price is HK$1,402
HK$1,897 total
includes taxes & fees
26 Apr - 27 Apr
The Royal Sonesta Chicago Downtown

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,719 reviews)
"We love staying here "
United States
Carrie
The price is HK$1,559
HK$2,060 total
includes taxes & fees
8 May - 9 May
Hilton Chicago

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, (3,886 reviews)
"Loved the stay here !"
United States
Alisha
The price is HK$1,199
HK$1,408 total
includes taxes & fees
26 Apr - 27 Apr
L7 Chicago by LOTTE

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, (2,150 reviews)
"Nice place to stay. "
United States
Akanksha
The price is HK$854
HK$1,186 total
includes taxes & fees
12 Apr - 13 Apr
The Godfrey Hotel Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (2,168 reviews)
"Great stay!"
United States
Hannah
The price is HK$909
HK$1,067 total
includes taxes & fees
12 Apr - 13 Apr
Club Quarters Hotel Wacker at Michigan, Chicago

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, (1,947 reviews)
"Hotel was really nice"
United States
LaCarr
The price is HK$989
HK$1,161 total
includes taxes & fees
30 Apr - 1 May
Hilton Garden Inn Chicago Downtown South Loop

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,248 reviews)
"Excellent stay."
United States
Fenton
The price is HK$1,826
HK$2,420 total
includes taxes & fees
15 Apr - 16 Apr
Swissotel - Chicago

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 7.3 km from Oakland
9.4 out of 10, Exceptional, (4,267 reviews)
"Loved it, would stay here everytime"
United States
KARELY
The price is HK$1,120
HK$1,315 total
includes taxes & fees
30 Apr - 1 May
citizenM Chicago Downtown

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (3,782 reviews)
"Great hotel "
United States
Marina
The price is HK$1,011
HK$1,407 total
includes taxes & fees
27 Apr - 28 Apr
Hotel Riu Plaza Chicago

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 6.9 km from Oakland
9.4 out of 10, Exceptional, (1,040 reviews)
"Lots of places to eat and shop nearby"
United States
Analicia
The price is HK$1,042
HK$1,452 total
includes taxes & fees
26 Apr - 27 Apr
Staypineapple, An Iconic Hotel, The Loop
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.

Magnificent Mile

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

O'Hare

Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago.

The Loop

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

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.

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 6 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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