Oakland Hotels, 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, (2,482 reviews)
"Great place to stay "
United States
Mark
The price is AU$361
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,504 reviews)
"Clean, friendly, modern, overall great stay!!"
United States
Jennifer
The price is AU$413
includes taxes & fees
24 May - 25 May
Hyatt Regency Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,296 reviews)
"Very good, would stay here again!"
United States
Lorena
The price is AU$376
includes taxes & fees
27 May - 28 May
Swissotel - Chicago

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (4,034 reviews)
"It was great property, amazing location and the breakfast was fantastic. "
United States
Nichole
The price is AU$261
includes taxes & fees
27 May - 28 May
Hotel Riu Plaza Chicago

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 7.4 km from Oakland
8.6 out of 10, Excellent, (1,626 reviews)
"It was very clean, beautiful place"
United States
Grisel
The price is AU$405
includes taxes & fees
25 May - 26 May
Sheraton Grand Chicago Riverwalk

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very good, (2,939 reviews)
"Great stay"
United States
Agnes Nmabila
The price is AU$170
includes taxes & fees
25 May - 26 May
Freehand Chicago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 7.6 km from Oakland
8.2 out of 10, Very good, (2,841 reviews)
"Great stay"
United States
Darin
The price is AU$275
includes taxes & fees
10 May - 11 May
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.6 out of 10, Excellent, (2,770 reviews)
"Clean room and great location "
United States
Diana
The price is AU$303
includes taxes & fees
25 May - 26 May
Hilton Chicago

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (10,134 reviews)
"Great stay"
United States
Matthew
The price is AU$207
includes taxes & fees
8 May - 9 May
Congress Plaza Hotel

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,218 reviews)
"The design of the property and location is great!"
United States
Fedna
The price is AU$246
includes taxes & fees
10 May - 11 May
Aloft Chicago Mag Mile

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, (3,682 reviews)
"Loved staying at this hotel"
United States
Kimberly Marie
The price is AU$339
includes taxes & fees
26 May - 27 May
LondonHouse Chicago, Curio Collection by Hilton

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
8.6 km from Oakland
9.4 out of 10, Exceptional, (2,433 reviews)
"Nice hotel centrally located "
United States
Stephen
The price is AU$396
includes taxes & fees
25 May - 26 May
Sofitel Chicago Magnificent Mile

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, (2,445 reviews)
"Great location, convenient, very welcoming"
United States
Claire
The price is AU$242
includes taxes & fees
10 May - 11 May
DoubleTree by Hilton Chicago - Magnificent Mile

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, (3,034 reviews)
"Great stay all around "
United States
Logan
The price is AU$377
includes taxes & fees
26 May - 27 May
InterContinental Chicago Magnificent Mile by IHG

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Streeterville, 8.6 km from Oakland
8.6 out of 10, Excellent, (2,446 reviews)
"Great place to stay."
United States
Yuge
The price is AU$243
includes taxes & fees
10 May - 11 May
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

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, (2,141 reviews)
"A great option to stay in the city! Nice hotel and friendly staff."
United States
Nicole
The price is AU$334
includes taxes & fees
8 May - 9 May
Fairmont Chicago at Millennium Park

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (5,156 reviews)
"Excellent location, very clean room and friendly staff"
United States
Alejandra
The price is AU$209
includes taxes & fees
25 May - 26 May
River Hotel

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, (2,428 reviews)
"We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff. "
United States
Cynthia
The price is AU$285
includes taxes & fees
25 May - 26 May
Palmer House a Hilton Hotel

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, (2,244 reviews)
"This was a great hotel. The staff and accommodations were terrific. I really enjoyed my stay "
United States
Alex
The price is AU$239
includes taxes & fees
25 May - 26 May
Silversmith Hotel Chicago Downtown

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, (3,412 reviews)
"Enjoyed our 5 night stay immensely"
United States
Marilyn
The price is AU$340
includes taxes & fees
26 May - 27 May
The Royal Sonesta Chicago Downtown
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.

Our guide on where to stay in Oakland

Find the best Oakland areas for the activities you enjoy most. Learn more about Oakland
Learn more about Oakland

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

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

The Loop

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

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.

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

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 5 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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