Oakland Hotels, Chicago

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Check prices for these dates

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

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4480 Cheap Hotels in Oakland - Specials, Reviews, & Last Minute Deals

Reception
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (3101)
"Excellent stay, close to everything and the staff was super nice "
United States
Kieata
The price is AU$216
includes taxes & fees
2 Nov - 3 Nov
Eurostars Magnificent Mile
Outdoor pool, pool cabanas (surcharge), pool umbrellas
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (2111)
"Great stay "
United States
Melinda
The price is AU$251
includes taxes & fees
16 Nov - 17 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Cocktail bar
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2874)
"Had a great stay!"
United States
Josh
The price is AU$227
includes taxes & fees
9 Nov - 10 Nov
Aloft Chicago Mag Mile
Reception
River Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (4758)
"Staff friendly and helpful..and accommodations just right..great location! "
United States
Adrienne
The price is AU$256
includes taxes & fees
3 Nov - 4 Nov
River Hotel
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4 out of 10, Exceptional, (2209)
"Rooms were clean with a great view of the lake and the city "
United States
Nathan
The price is AU$339
includes taxes & fees
12 Nov - 13 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
Cocktail bar
Freehand Chicago
Freehand Chicago
4.0 star property
8.0 out of 10, Very good, (2505)
"Super clean, very good staff services, very convenient location, quiet, easy checking in and out "
United States
Lixiao
The price is AU$147
includes taxes & fees
11 Nov - 12 Nov
Freehand Chicago
Terrace/patio
citizenM Chicago Downtown
citizenM Chicago Downtown
4.0 star property
9.4 out of 10, Exceptional, (3980)
"Great place to stay. "
United States
sherry
The price is AU$236
includes taxes & fees
9 Nov - 10 Nov
citizenM Chicago Downtown
Banquet hall
Congress Plaza Hotel
Congress Plaza Hotel
3.5 star property
8.0 out of 10, Very good, (9525)
"Excellent location very convenient parking nice staff clean rooms"
United States
Mike
The price is AU$306
includes taxes & fees
2 Nov - 3 Nov
Congress Plaza Hotel
Exterior
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
8.4 out of 10, Very good, (4113)
"This hotel had a great location to shopping and several enjoyable restaurants."
United States
laura
The price is AU$222
includes taxes & fees
11 Nov - 12 Nov
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Ballroom
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 star property
8.8 out of 10, Excellent, (3158)
"Our stay was great"
United States
Bruce E
The price is AU$206
includes taxes & fees
16 Nov - 17 Nov
Hilton Chicago/Magnificent Mile Suites
Exterior
Hilton Chicago
Hilton Chicago
4.0 star property
8.4 out of 10, Very good, (2282)
"We loved this hotel it was beautiful and convenient . "
United States
Daniel
The price is AU$376
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
Rooftop terrace
Best Western River North Hotel
Best Western River North Hotel
2.5 star property
7.8 out of 10, Good, (1034)
"Great stay"
Australia
Bart
The price is AU$182
includes taxes & fees
9 Nov - 10 Nov
Best Western River North Hotel
Exterior
FOUND Hotel Chicago River North
FOUND Hotel Chicago River North
2.0 star property
8.2 out of 10, Very good, (280)
"Perfect location! Tons of restaurants and shopping nearby! "
United States
MaryJane
The price is AU$137
includes taxes & fees
10 Nov - 11 Nov
FOUND Hotel Chicago River North
Front of property
Hotel Riu Plaza Chicago
Hotel Riu Plaza Chicago
4.0 star property
9.4 out of 10, Exceptional, (2628)
"Great place to stay "
United States
Larry William
The price is AU$276
includes taxes & fees
9 Nov - 10 Nov
Hotel Riu Plaza Chicago
American cuisine
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 star property
9.0 out of 10, Wonderful, (1620)
"Great Hotel"
United States
Cesar
The price is AU$213
includes taxes & fees
16 Nov - 17 Nov
Crowne Plaza Chicago West Loop by IHG
Bar (on property)
voco Chicago Downtown - Riverwalk by IHG
voco Chicago Downtown - Riverwalk by IHG
3.5 star property
8.8 out of 10, Excellent, (3239)
"Great location and fantastic staff who were always happy to help. "
United Kingdom
Victoria
The price is AU$317
includes taxes & fees
9 Nov - 10 Nov
voco Chicago Downtown - Riverwalk by IHG
Exterior
La Quinta Inn & Suites by Wyndham Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
8.6 out of 10, Excellent, (2605)
"Good place to stay"
United States
vijay
The price is AU$253
includes taxes & fees
16 Nov - 17 Nov
La Quinta Inn & Suites by Wyndham Chicago Downtown
Rooftop terrace
Hyatt Centric The Loop Chicago
Hyatt Centric The Loop Chicago
4.0 star property
9.0 out of 10, Wonderful, (2197)
"It was an amazing stay!"
United States
Kristy S
The price is AU$268
includes taxes & fees
16 Nov - 17 Nov
Hyatt Centric The Loop Chicago
Lobby
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago Downtown
4.0 star property
9.4 out of 10, Exceptional, (2023)
"Great place to stay "
United States
Cheryl
Silversmith Hotel Chicago Downtown
Ballroom
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 star property
8.4 out of 10, Very good, (2030)
"Great place to stay."
United States
Ron
The price is AU$352
includes taxes & fees
16 Nov - 17 Nov
Palmer House a Hilton 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. 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 a city and modern architecture

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Top Oakland Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"I like it"
mitzie 1-night trip
Posted 2 days ago
Congress Plaza Hotel

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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