Hotels in Oakland

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Check prices for these dates

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

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Our top choices for Oakland hotels

Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 7.9 km from Oakland
8.0 out of 10, Very good, (2658)
"It's an excellent place."
United States
Jose
The price is S$111
includes taxes & fees
4 Jan - 5 Jan, 2026
Freehand Chicago
Banquet hall
Congress Plaza Hotel

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 6 km from Oakland
8.0 out of 10, Very good, (9697)
"Wonderful stay!"
United States
Zach
The price is S$312
includes taxes & fees
31 Dec - 1 Jan, 2026
Congress Plaza Hotel
Reception
River Hotel

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (4856)
"Great location, comfortable room, and nice staff."
United States
Claudia
The price is S$113
includes taxes & fees
25 Dec - 26 Dec
River Hotel
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 7.9 km from Oakland
8.6 out of 10, Excellent, (2964)
"Great place to stay"
United States
Elisha
The price is S$130
includes taxes & fees
22 Jan - 23 Jan, 2026
Aloft Chicago Mag Mile
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
8.2 out of 10, Very good, (2761)
"Excellent place to stay "
United States
Teniesha
The price is S$165
includes taxes & fees
6 Jan - 7 Jan, 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Terrace/patio
DoubleTree by Hilton 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, (2198)
"Great location, easy parking. "
United States
Maria
The price is S$129
includes taxes & fees
7 Jan - 8 Jan, 2026
DoubleTree by Hilton Chicago - Magnificent Mile
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 7.3 km from Oakland
9.4 out of 10, Exceptional, (3417)
"The Hotel was amazing great location "
United States
Donnisha
The price is S$256
includes taxes & fees
20 Jan - 21 Jan, 2026
Hyatt Regency Chicago
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, (2284)
"Great staff and restaurants!!"
United States
Abigale
The price is S$173
includes taxes & fees
20 Jan - 21 Jan, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Bar (on property)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

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, (4279)
"Friendly Staff, clean room, great area"
United States
LaTia
The price is S$117
includes taxes & fees
4 Jan - 5 Jan, 2026
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Premium bedding, down duvets, pillow-top beds, in-room safe
The Wade

The Wade

The Wade
4.5 star property
Streeterville, 7.9 km from Oakland
8.4 out of 10, Very good, (1532)
"Great staff and great location. "
United States
Joe
The price is S$140
includes taxes & fees
4 Jan - 5 Jan, 2026
The Wade
Exterior
Arlo Chicago

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 7.1 km from Oakland
9.2 out of 10, Wonderful, (1901)
"Great location, friendly staff rooms were great and clean."
United States
Derrick
The price is S$167
includes taxes & fees
3 Jan - 4 Jan, 2026
Arlo Chicago
Lobby sitting area
Warwick Allerton - Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Magnificent Mile, 8.1 km from Oakland
8.4 out of 10, Very good, (3006)
"Enjoyed this hotel stay. "
United States
Kimberly
The price is S$158
includes taxes & fees
28 Dec - 29 Dec
Warwick Allerton - Chicago
Lobby sitting area
Club Quarters Hotel Wacker at Michigan, 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, (2014)
"Great stay"
United States
Kramer
The price is S$113
includes taxes & fees
25 Dec - 26 Dec
Club Quarters Hotel Wacker at Michigan, Chicago
Breakfast, lunch and dinner served
Club Quarters Hotel, Central Loop, Chicago

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, (3330)
"Great hotel "
United States
Anthony
The price is S$113
includes taxes & fees
25 Dec - 26 Dec
Club Quarters Hotel, Central Loop, Chicago
Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe
The Whitehall Hotel, BW Premier Collection

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, (3789)
"Clean room, good location, friendly staff"
United States
Zacharias
The price is S$115
includes taxes & fees
5 Jan - 6 Jan, 2026
The Whitehall Hotel, BW Premier Collection
Exterior
Hyatt Centric Chicago Magnificent Mile

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, (1051)
"Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food."
United States
Hannah
The price is S$185
includes taxes & fees
1 Jan - 2 Jan, 2026
Hyatt Centric Chicago Magnificent Mile
Exterior
Hilton Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 5.7 km from Oakland
8.4 out of 10, Very good, (2411)
"The room was clean and the staff was outstanding. "
United States
Albert
The price is S$222
includes taxes & fees
1 Jan - 2 Jan, 2026
Hilton Chicago
Lobby
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, (3456)
"Great hotel! "
United States
Kianna
The price is S$197
includes taxes & fees
4 Jan - 5 Jan, 2026
LondonHouse Chicago, Curio Collection by Hilton
Lobby
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
River North, 8 km from Oakland
8.6 out of 10, Excellent, (5441)
"Perfect location, clean, delicious breakfast, and overall highly recommended. "
United States
Neftali
The price is S$142
includes taxes & fees
4 Jan - 5 Jan, 2026
Embassy Suites by Hilton Chicago Downtown River North
Exterior
La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
The Loop, 7 km from Oakland
8.6 out of 10, Excellent, (2627)
"Great place"
United States
Uvirkaa
The price is S$144
includes taxes & fees
4 Jan - 5 Jan, 2026
La Quinta Inn & Suites by Wyndham 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.
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Where to stay in Oakland

Find the best Oakland areas for the activities you enjoy most.
Downtown Chicago which includes 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 featuring 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

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 which includes 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

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

10/10 Excellent
"The staff were wonderful! The only thing I missed in the room was a desk."
Lillian 4-night trip
Posted 1 day ago
Silversmith Hotel Chicago Downtown

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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