Oakland Hotels, Chicago

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Tonight
18 Dec - 19 Dec
Tomorrow
19 Dec - 20 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

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Our top choices for Oakland hotels

Exterior
Claridge House Chicago, Tapestry Collection by Hilton

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, (1482)
"I really liked this location - we will stay here again. "
United States
Lynnsey
The price is AU$160
includes taxes & fees
28 Dec - 29 Dec
Claridge House Chicago, Tapestry Collection by Hilton
Meeting facility
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt
4.5 star property
Gold Coast, 8.9 km from Oakland
9.2 out of 10, Wonderful, (1293)
"Great hotel!"
United States
Julie
The price is AU$283
includes taxes & fees
9 Jan - 10 Jan 2026
Thompson Chicago, by Hyatt
Serves breakfast, lunch and dinner
Moxy Chicago Downtown

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
River North, 8 km from Oakland
9.4 out of 10, Exceptional, (854)
"Great place to stay"
United States
Mason
The price is AU$200
includes taxes & fees
28 Dec - 29 Dec
Moxy Chicago Downtown
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (2268)
"Great staff and restaurants!!"
United States
Abigale
The price is AU$212
includes taxes & fees
15 Jan - 16 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3.0 star property
7.5 km from Oakland
9.2 out of 10, Wonderful, (1000)
"Good place to stay in."
United States
Joan
The price is AU$231
includes taxes & fees
3 Jan - 4 Jan 2026
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
2 restaurants, breakfast, lunch, dinner served; Mediterranean cuisine
The Hoxton Chicago

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Fulton Market, 7.7 km from Oakland
9.0 out of 10, Wonderful, (1008)
"Awesome hotel"
United States
Eligija
The Hoxton Chicago
Exterior
Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North
3.5 star property
River North, 7.6 km from Oakland
9.2 out of 10, Wonderful, (1001)
"Great location, great hotel, friendly staff "
United States
Eric
The price is AU$197
includes taxes & fees
1 Jan - 2 Jan 2026
Springhill Suites by Marriott Chicago Downtown/ River North
Exterior
Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
7.5 km from Oakland
9.2 out of 10, Wonderful, (1000)
"Staff was so friendly Hotel was so clean and spacious!!! Loved the bed!! "
United States
Denise
The price is AU$224
includes taxes & fees
3 Jan - 4 Jan 2026
Hampton Inn Chicago West Loop Fulton Market Area
City view from property
Hyatt House Chicago West Loop

Hyatt House Chicago West Loop

Hyatt House Chicago West Loop
3.5 star property
Fulton Market, 7.9 km from Oakland
8.8 out of 10, Excellent, (1132)
"I always come back to this Hotel everything is close the area is full of things to do really love staying here !!"
United States
Sandra
The price is AU$240
includes taxes & fees
25 Dec - 26 Dec
Hyatt House Chicago West Loop
Lobby
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
2.5 star property
Streeterville, 7.9 km from Oakland
9.0 out of 10, Wonderful, (1006)
"The room was huge, great stay, clean, convenient, comfortable and great staff. "
United States
Madeline
The price is AU$142
includes taxes & fees
22 Dec - 23 Dec
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Lunch and dinner served
Radisson Blu Aqua Hotel Chicago

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, (1788)
"Great hotel, close to shopping and restaurants, excellent customer service, highly recommend."
United States
Gina
The price is AU$276
includes taxes & fees
16 Jan - 17 Jan 2026
Radisson Blu Aqua Hotel Chicago
Exterior detail
The Emily Hotel

The Emily Hotel

The Emily Hotel
4.0 star property
Fulton Market, 8.1 km from Oakland
9.2 out of 10, Wonderful, (1283)
"Very pleasant stay for my birthday! Will definitely come back and recommend to others! Top notch service and rooms were beautiful and comfortable!"
United States
Daniela
The Emily Hotel
Lobby
The Chicago Hotel Collection Ambassador Gold Coast

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, (1260)
"Solid stay in a great part of town"
United States
Michael
The price is AU$229
includes taxes & fees
19 Dec - 20 Dec
The Chicago Hotel Collection Ambassador Gold Coast
Daily cooked-to-order breakfast for a fee
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
8.5 km from Oakland
9.4 out of 10, Exceptional, (2272)
"Great location, nice bar."
United States
Erik
The price is AU$331
includes taxes & fees
21 Dec - 22 Dec
Sofitel Chicago Magnificent Mile
Exterior
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG
3.0 star property
River North, 7.7 km from Oakland
8.8 out of 10, Excellent, (2047)
"Great hotel."
United States
Mario
The price is AU$189
includes taxes & fees
8 Jan - 9 Jan 2026
Holiday Inn Chicago Dwtn - The Mart by IHG
Free daily buffet breakfast
Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport
2.5 star property
27.3 km from Oakland
9.2 out of 10, Wonderful, (2125)
"Staff was super friendly. "
United States
David
The price is AU$164
includes taxes & fees
22 Dec - 23 Dec
Hampton Inn Chicago-O'Hare International Airport
2 restaurants, breakfast, lunch, dinner served; American cuisine
LondonHouse Chicago, Curio Collection by Hilton

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, (3424)
"Loved the location and view!"
United States
Erica
The price is AU$231
includes taxes & fees
18 Jan - 19 Jan 2026
LondonHouse Chicago, Curio Collection by Hilton
View from property
Courtyard by Marriott Chicago Downtown River North

Courtyard by Marriott Chicago Downtown River North

Courtyard by Marriott Chicago Downtown River North
3.0 star property
River North, 7.7 km from Oakland
8.8 out of 10, Excellent, (1001)
"Super customer service! We will definitely stay here again!"
United States
AMANDA S
The price is AU$181
includes taxes & fees
9 Jan - 10 Jan 2026
Courtyard by Marriott Chicago Downtown River North
Exterior
Embassy Suites by Hilton Chicago Downtown 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
8.4 out of 10, Very good, (2750)
"Excellent place to stay "
United States
Teniesha
The price is AU$193
includes taxes & fees
11 Jan - 12 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
View from property
Fairfield Inn & Suites Chicago Downtown/River North

Fairfield Inn & Suites Chicago Downtown/River North

Fairfield Inn & Suites Chicago Downtown/River North
3.0 star property
River North, 7.8 km from Oakland
9.2 out of 10, Wonderful, (1188)
"Good location, good staff."
United States
Andrew
The price is AU$172
includes taxes & fees
4 Jan - 5 Jan 2026
Fairfield Inn & Suites Chicago Downtown/River North
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.
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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 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.

Magnificent Mile - River North

Magnificent Mile

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

The Loop - Downtown which includes a river or creek

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.

Chicago showing rides

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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Clean Room"
Zaire 2-night trip
Posted 14 hours ago
Hilton Chicago/Magnificent Mile Suites

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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