Oakland Hotels, Chicago

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Our top choices for Oakland hotels

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very good, (2686)
"Quite area in a good location to walk to different locations."
United States
John steve
The price is NZ$131
includes taxes & fees
14 Jan - 15 Jan
Freehand 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, (3099)
"Second time to stay here, everything is great!"
United States
Wei
The price is NZ$252
includes taxes & fees
5 Jan - 6 Jan
Hotel Riu Plaza Chicago

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (4890)
"Would stay there again"
United States
Zach
The price is NZ$166
includes taxes & fees
16 Jan - 17 Jan
River Hotel

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, (2313)
"Great stay!"
United States
Angela
The price is NZ$265
includes taxes & fees
20 Jan - 21 Jan
Sable at Navy Pier Chicago, Curio Collection by Hilton

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (3008)
"Great place to stay"
United States
Elisha
The price is NZ$169
includes taxes & fees
6 Jan - 7 Jan
Aloft Chicago Mag Mile

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Gold Coast, 9.3 km from Oakland
9.0 out of 10, Wonderful, (1506)
"Nice stay"
United States
Michelle
The price is NZ$174
includes taxes & fees
1 Feb - 2 Feb
Claridge House Chicago, Tapestry Collection by Hilton

The Wade

The Wade
4.5 star property
Streeterville, 7.9 km from Oakland
8.4 out of 10, Very good, (1569)
"Easy check in and out, excellent room service and dining menu."
United States
Kevin Bradford
The price is NZ$189
includes taxes & fees
8 Jan - 9 Jan
The Wade

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, (2218)
"Fantastic stay! Looking forward to staying here again!!"
United States
Amber
The price is NZ$174
includes taxes & fees
11 Jan - 12 Jan
DoubleTree by Hilton Chicago - Magnificent Mile

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, (2802)
"Great hotel staff and location. "
United States
Jacqueline
The price is NZ$227
includes taxes & fees
11 Jan - 12 Jan
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

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, (3662)
"Great hotel"
United States
Jeanette
The price is NZ$182
includes taxes & fees
11 Jan - 12 Jan
Hilton Chicago/Magnificent Mile Suites

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 8.1 km from Oakland
9.0 out of 10, Wonderful, (3181)
"stunning hotel"
Canada
Yiwei
The price is NZ$190
includes taxes & fees
2 Feb - 3 Feb
Eurostars Magnificent Mile

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Magnificent Mile, 8.1 km from Oakland
8.4 out of 10, Very good, (3019)
"Every thing is perfect, the location, safe for solo travel. "
United States
Ken
The price is NZ$178
includes taxes & fees
25 Jan - 26 Jan
Warwick Allerton - 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, (2032)
"Great stay"
United States
Kramer
The price is NZ$166
includes taxes & fees
16 Jan - 17 Jan
Club Quarters Hotel Wacker at Michigan, Chicago

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
River North, 8.3 km from Oakland
8.6 out of 10, Excellent, (1971)
"The room was nice, the area was perfect for walking distance for food and activities. "
United States
Alexis
The price is NZ$218
includes taxes & fees
1 Feb - 2 Feb
The Godfrey Hotel Chicago

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 7.3 km from Oakland
9.4 out of 10, Exceptional, (4146)
"Great hotel"
United States
Richard
The price is NZ$206
includes taxes & fees
8 Jan - 9 Jan
citizenM Chicago Downtown

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 8.6 km from Oakland
8.2 out of 10, Very good, (3846)
" Breakfast is good, location is excellent, service staff is courteous."
United States
Luis
The price is NZ$156
includes taxes & fees
5 Jan - 6 Jan
The Whitehall Hotel, BW Premier Collection

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, (3219)
"Excellent location and the hotel is amazing I will definitely recommend "
United States
Diana Sofia Cruz
The price is NZ$298
includes taxes & fees
1 Feb - 2 Feb
The Royal Sonesta Chicago Downtown

Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Theatre District, 6.7 km from Oakland
9.0 out of 10, Wonderful, (2340)
"Great hotel!!"
United States
Juancarlos
The price is NZ$244
includes taxes & fees
9 Jan - 10 Jan
Hyatt Centric The Loop Chicago

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
River North, 7.8 km from Oakland
8.6 out of 10, Excellent, (4311)
"Amazing staff and perfect location "
United States
Brandi
The price is NZ$159
includes taxes & fees
11 Jan - 12 Jan
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 6.6 km from Oakland
8.8 out of 10, Excellent, (3355)
"Great hotel "
United States
Anthony
The price is NZ$166
includes taxes & fees
16 Jan - 17 Jan
Club Quarters Hotel, Central Loop, Chicago
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.

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

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

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.

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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