Oakland Hotels, Chicago

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Check prices for these dates

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

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, (2650)
"The room was spotless and the staff where great!"
United States
Maria
The price is AU$130
includes taxes & fees
5 Jan - 6 Jan 2026
Freehand Chicago
Lobby
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, (2969)
"The room was very clean, the location was excellent."
United States
Craig
The price is AU$140
includes taxes & fees
14 Jan - 15 Jan 2026
Aloft Chicago Mag Mile
Lobby
River Hotel

River Hotel

River Hotel
4.0 star property
The Loop, 7.4 km from Oakland
8.8 out of 10, Excellent, (4861)
"Great location, comfortable room, and nice staff."
United States
Claudia
The price is AU$137
includes taxes & fees
18 Jan - 19 Jan 2026
River Hotel
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, (3411)
"The Hotel was amazing great location "
United States
Donnisha
The price is AU$292
includes taxes & fees
5 Jan - 6 Jan 2026
Hyatt Regency Chicago
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
Reception
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 6.7 km from Oakland
8.4 out of 10, Very good, (2144)
"Beautiful hotel! Perfect for a holiday staycation! "
United States
Melissa
The price is AU$242
includes taxes & fees
28 Dec - 29 Dec
Palmer House a Hilton Hotel
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
Exterior
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, (3018)
"Enjoyed this hotel stay. "
United States
Kimberly
The price is AU$160
includes taxes & fees
4 Jan - 5 Jan 2026
Warwick Allerton - Chicago
Bar (on property)
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, (3782)
"Clean room, good location, friendly staff"
United States
Zacharias
The price is AU$136
includes taxes & fees
4 Jan - 5 Jan 2026
The Whitehall Hotel, BW Premier Collection
Exterior
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
River North, 7.7 km from Oakland
8.8 out of 10, Excellent, (3486)
"Very helpful staff, clean rooms and really great breakfast buffet. "
United States
Katherine
The price is AU$192
includes taxes & fees
21 Dec - 22 Dec
voco Chicago Downtown - Riverwalk by IHG
Nightclub
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, (3320)
"Great hotel "
United States
Anthony
The price is AU$148
includes taxes & fees
21 Dec - 22 Dec
Club Quarters Hotel, Central Loop, Chicago
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, (2191)
"Very friendly staff, clean rooms, the location is amazing and near of everything "
United States
Sarwat
The price is AU$158
includes taxes & fees
25 Dec - 26 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
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, (1994)
"A good place for stay "
United States
Julio
The price is AU$148
includes taxes & fees
21 Dec - 22 Dec
Club Quarters Hotel Wacker at Michigan, Chicago
Indoor pool
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
8.4 out of 10, Very good, (4253)
"Excellent location Restaurant attached "
United States
Rebecca
The price is AU$152
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Lobby
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, (9673)
"Wonderful stay!"
United States
Zach
The price is AU$367
includes taxes & fees
31 Dec - 1 Jan 2026
Congress Plaza Hotel
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, (2383)
"Great amenities and staff"
United States
Edward J
The price is AU$246
includes taxes & fees
25 Dec - 26 Dec
Hilton Chicago
Lobby
Silversmith Hotel Chicago Downtown

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, (2128)
"Hotel is beautiful, staff was very kind. "
United States
Lauren
Silversmith Hotel Chicago Downtown
Restaurant
Hyatt Centric The Loop Chicago

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, (2307)
"Very nice clean hotel! "
United States
Jodee
The price is AU$242
includes taxes & fees
25 Dec - 26 Dec
Hyatt Centric The Loop Chicago
Lobby
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 5.9 km from Oakland
7.4 out of 10, Good, (2494)
"Always a good stay"
Canada
Domenic
The price is AU$140
includes taxes & fees
12 Jan - 13 Jan 2026
Travelodge by Wyndham Downtown Chicago
Pool
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 5.4 km from Oakland
8.8 out of 10, Excellent, (1763)
"Great check in and responsive front desk staff. Housekeeping staff did a great job during our visit! "
United States
Steven
The price is AU$129
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Garden Inn Chicago Downtown South Loop
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

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"The inside Italian restaurant was fabulous."
Raymond 2-night trip
Posted 11 hours ago
Embassy Suites by Hilton Chicago Downtown River North

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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