Oakland Hotels, Chicago

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Check prices for these dates

Tonight
21 Feb - 22 Feb
Tomorrow
22 Feb - 23 Feb
Next weekend
27 Feb - 1 Mar
In two weeks
6 Mar - 8 Mar

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Our top choices for Oakland hotels

Terrace/patio

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, (2,384 reviews)
"Great stay"
United States
Blake
The price is NZ$325
includes taxes & fees
23 Feb - 24 Feb
Sable at Navy Pier Chicago, Curio Collection by Hilton
Room service – dining

The Wade

The Wade
4.5 star property
Streeterville, 7.9 km from Oakland
8.4 out of 10, Very good, (1,684 reviews)
"Thoroughly enjoyed my stay at The Wade"
United States
Danielle
The price is NZ$194
includes taxes & fees
1 Mar - 2 Mar
The Wade
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
7.2 km from Oakland
9.0 out of 10, Wonderful, (3,208 reviews)
"Place is always top notch..stay here anytime we stay in Chicago."
United States
Jon
The price is NZ$298
includes taxes & fees
22 Feb - 23 Feb
Swissotel - Chicago
Terrace/patio

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, (2,324 reviews)
"Great staff, room spotless, great price."
United States
Robert
The price is NZ$208
includes taxes & fees
1 Mar - 2 Mar
DoubleTree by Hilton Chicago - Magnificent Mile
Exterior

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, (2,829 reviews)
"Great stay "
United States
Rudy
The price is NZ$260
includes taxes & fees
1 Mar - 2 Mar
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Lunch and dinner served

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, (1,870 reviews)
"Room was very nice, views were fantastic and the restaurant was excellent "
United States
Michael
The price is NZ$359
includes taxes & fees
22 Feb - 23 Feb
Radisson Blu Aqua Hotel Chicago
Executive lounge

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 7.1 km from Oakland
8.6 out of 10, Excellent, (2,071 reviews)
"Great place "
United States
Kamilah
The price is NZ$391
includes taxes & fees
1 Mar - 2 Mar
Fairmont Chicago at Millennium Park
Lobby

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3,097 reviews)
"Great location and friendly staff. "
United States
Pablo
The price is NZ$169
includes taxes & fees
22 Feb - 23 Feb
Aloft Chicago Mag Mile
Bar (on property)

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (1,131 reviews)
"I always stay here when in town. "
United States
Jeffrey
Ivy Boutique Hotel
Lobby

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, (2,412 reviews)
"Can't wait to go back love the hotel and the location was great."
United States
eyulonda
The price is NZ$195
includes taxes & fees
22 Feb - 23 Feb
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Exterior

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, (3,819 reviews)
"The staff and the cleanliness of the Hotel was amazing and the views where great!!"
United States
Oliver
The price is NZ$190
includes taxes & fees
27 Feb - 28 Feb
Hilton Chicago/Magnificent Mile Suites
Ballroom

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago
4.0 star property
Streeterville, 8.6 km from Oakland
8.6 out of 10, Excellent, (2,005 reviews)
"Very clean, quiet, and warm reception and service from the staff. "
United States
tim
The price is NZ$200
includes taxes & fees
24 Feb - 25 Feb
Millennium Knickerbocker Chicago
2 bars/lounges

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3,483 reviews)
"Clean room, great staff, great location "
United States
Tiffany
The price is NZ$414
includes taxes & fees
22 Feb - 23 Feb
Hyatt Regency Chicago
Exterior

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Streeterville, 8 km from Oakland
9.0 out of 10, Wonderful, (1,079 reviews)
"Amazing location, excellent service and great pool and hot tub. "
United States
Tim
The price is NZ$299
includes taxes & fees
27 Feb - 28 Feb
Hyatt Centric Chicago Magnificent Mile
Premium bedding, in-room safe, desk, blackout curtains

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, (1,764 reviews)
"Great location and perfect for quick trips!"
United States
Andres
The price is NZ$207
includes taxes & fees
26 Feb - 27 Feb
Courtyard by Marriott Chicago Magnificent Mile
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 8.2 km from Oakland
7.6 out of 10, Good, (1,214 reviews)
"Amazing stay "
United States
Napoleon
The Chicago Hotel Collection - Magnificent Mile
Exterior

Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile
2.5 star property
Streeterville, 8.1 km from Oakland
8.0 out of 10, Very good, (1,408 reviews)
"Great hotel,, like so much"
United States
Ilham
The price is NZ$176
includes taxes & fees
25 Feb - 26 Feb
Hampton Inn Chicago Downtown/Magnificent Mile
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 7.9 km from Oakland
9.4 out of 10, Exceptional, (3,381 reviews)
"Amazing place, breakfast is great , location is great - honestly great hotel! "
United States
Brisa
The price is NZ$242
includes taxes & fees
4 Mar - 5 Mar
Hotel Riu Plaza Chicago
View from property

The Blackstone, Autograph Collection

The Blackstone, Autograph Collection
4.0 star property
The Loop, 5.8 km from Oakland
9.0 out of 10, Wonderful, (1,002 reviews)
"Beautiful place to stay, nice staff 🙏"
United States
Yu Ching Dexter
The price is NZ$308
includes taxes & fees
22 Feb - 23 Feb
The Blackstone, Autograph Collection
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (9,920 reviews)
"Great location, beautiful historic hotel with clean, updated rooms. "
United States
Jennifer
Congress Plaza Hotel
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

Our guide on where to stay in Oakland

Find the best Oakland areas for the activities you enjoy most.
Downtown Chicago featuring a city

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.

Water Tower Place

Magnificent Mile

An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

The Loop - Downtown which includes a river or creek

The Loop

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

River North showing railway items, street scenes and a 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.

Underground passage in the Chicago O'Hare airport

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.

Top Oakland Hotel Reviews

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

10/10 Excellent
"clean, convenient, friendly staff "
Jennifer 1-night trip
Posted 2 days ago
Hilton Chicago O'Hare Airport

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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