Chicago Hotel Guide. Hotels in Oakland, Chicago, United States of America

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
17 Oct - 19 Oct
Next weekend
24 Oct - 26 Oct

Filter by

Guest rating
Guest rating
Star rating

Top Trending Hotels Near Oakland, Chicago

Reception
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (3080)
"Very nice location and everything was a 10/10"
The price is €110
includes taxes & fees
12 Nov - 13 Nov
Eurostars Magnificent Mile
Cocktail bar
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2862)
"Had a great stay!"
The price is €140
includes taxes & fees
9 Nov - 10 Nov
Aloft Chicago Mag 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, (2090)
"Great hotel"
The price is €161
includes taxes & fees
4 Nov - 5 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
River Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (4745)
"Staff friendly and helpful..and accommodations just right..great location! "
The price is €161
includes taxes & fees
26 Oct - 27 Oct
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, (2184)
"Great hotel "
The price is €191
includes taxes & fees
9 Nov - 10 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, (2466)
"Great place"
The price is €97
includes taxes & fees
10 Nov - 11 Nov
Freehand Chicago
Banquet hall
Congress Plaza Hotel
Congress Plaza Hotel
3.5 star property
8.0 out of 10, Very good, (9406)
"Beautiful hotel!"
The price is €129
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, (4077)
"We definitely will stay there again place was very nice "
The price is €172
includes taxes & fees
9 Nov - 10 Nov
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Terrace/patio
citizenM Chicago Downtown
citizenM Chicago Downtown
4.0 star property
9.2 out of 10, Wonderful, (3950)
"Great place to stay. "
The price is €133
includes taxes & fees
9 Nov - 10 Nov
citizenM Chicago Downtown
Ballroom
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 star property
8.8 out of 10, Excellent, (3098)
"Our stay was great"
The price is €146
includes taxes & fees
9 Nov - 10 Nov
Hilton Chicago/Magnificent Mile Suites
Exterior
Hilton Chicago
Hilton Chicago
4.0 star property
8.4 out of 10, Very good, (2257)
"We loved this hotel it was beautiful and convenient . "
The price is €212
includes taxes & fees
23 Oct - 24 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, (1025)
"Great stay"
The price is €102
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, (273)
"Perfect location! Tons of restaurants and shopping nearby! "
The price is €82
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, (2595)
"Great place to stay "
The price is €168
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, (1595)
"Great Hotel"
The price is €132
includes taxes & fees
9 Nov - 10 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, (3208)
"Great stay "
The price is €162
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, (2583)
"Good place to stay"
The price is €160
includes taxes & fees
9 Nov - 10 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, (2177)
"It was an amazing stay!"
The price is €184
includes taxes & fees
9 Nov - 10 Nov
Hyatt Centric The Loop Chicago
Ballroom
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 star property
8.4 out of 10, Very good, (2015)
"Great place to stay."
The price is €203
includes taxes & fees
30 Oct - 31 Oct
Palmer House a Hilton Hotel
Lobby
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2.0 star property
7.4 out of 10, Good, (2409)
"Comfortable bed, bright room, good shower, very accessible location."
The price is €97
includes taxes & fees
12 Nov - 13 Nov
Travelodge by Wyndham Downtown 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

The Loop - Downtown showing 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 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

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Excellent
"The room was clean and had the best view! Love all the close restaurants and things to do ."
Lori 2-night trip
Posted 17 hours ago
Sable at Navy Pier Chicago, Curio Collection by Hilton

Explore a world of travel with Expedia

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 6 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.