Search Chalets in Chicago

  • 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

Find holiday rentals that suit your style

apart-hotel image
Aparthotels
Aparthotels
Apartment image
Apartments
Apartments

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan
No exact matches found, but these alternatives could be just right

Recommended hotels in Chicago

A hotel entrance with a marquee sign, a blue carpet, and a flag.

1. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,210 reviews)
"Great location from both airports. Lovely hotel clean and convenient"
United Kingdom
Kanokkan
The price is S$170
includes taxes & fees
10 Dec - 11 Dec
Hilton Vacation Club Hotel Blake Chicago
A hotel entrance with a sign for the Club Quarters Hotel, number 75, and a River Hotel sign.

2. River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,619 reviews)
"Great location and lovely staff"
United States
Jillian
The price is S$152
includes taxes & fees
14 Dec - 15 Dec
River Hotel
A cityscape at dusk with high-rise buildings, including a Hilton hotel.

3. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (5,071 reviews)
"Great place to stay"
United States
Melissa
The price is S$157
includes taxes & fees
10 Dec - 11 Dec
Hilton Chicago/Magnificent Mile Suites
A rooftop terrace with outdoor seating and a view of the city skyline.

4. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,903 reviews)
"Great Location"
United States
Natasha
The price is S$258
includes taxes & fees
23 Nov - 24 Nov
LondonHouse Chicago, Curio Collection by Hilton
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

5. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,588 reviews)
"Great location and beautiful hotel!"
United States
Jodi
The price is S$148
includes taxes & fees
7 Dec - 8 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
The exterior of the Swissotel building with its distinctive glass facade and the hotel's name displayed prominently.

6. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,589 reviews)
"Great hotel"
United States
Daniel Michael
The price is S$237
includes taxes & fees
13 Dec - 14 Dec
Swissotel - Chicago
A multi-story hotel with a prominent 'La Quinta' sign, featuring a modern architectural design with large windows and a flat facade.

7. La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2,960 reviews)
"Great location."
United States
Sahithi
The price is S$175
includes taxes & fees
23 Nov - 24 Nov
La Quinta Inn & Suites by Wyndham Chicago Downtown
A cityscape with modern high-rise buildings, a river, and a boat.

8. Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,503 reviews)
"Wonderful will stay again"
United States
Kristee
The price is S$284
includes taxes & fees
22 Nov - 23 Nov
Hyatt Regency Chicago
The entrance of L7 Hotels by Lotte, featuring a modern facade with large windows and a glass entrance.

9. L7 CHICAGO by LOTTE HOTELS

L7 CHICAGO by LOTTE HOTELS
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (5,250 reviews)
"Great location, helpful staff. Would stay again."
United States
Cory
The price is S$227
includes taxes & fees
16 Dec - 17 Dec
L7 CHICAGO by LOTTE HOTELS
A poolside area with lounge chairs and a reflection of the surrounding buildings.

10. Hotel 505 River North

Hotel 505 River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (3,026 reviews)
"Great location, reasonably rates and a staff that made us feel like we were home from the minute we pulled up to the front of the hotel."
United States
Melvin
The price is S$237
includes taxes & fees
16 Dec - 17 Dec
Hotel 505 River North
A couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.

11. Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,423 reviews)
"I really liked the hotel and location"
United States
Eric
The price is S$131
includes taxes & fees
22 Nov - 23 Nov
Hotel Saint Clair- Magnificent Mile
A building with a marquee reading 'ACME HOTEL COMPANY' and a sign stating 'ACME HOTEL NOT VACANCY'.

12. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,932 reviews)
"Hotel is great for the price."
United States
alex
The price is S$130
includes taxes & fees
7 Dec - 8 Dec
ACME Hotel Chicago, Outset Collection by Hilton
A grand lobby with a staircase, ornate chandeliers, and a clock on the wall.

13. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,729 reviews)
"Beautiful hotel with wonderful staff!"
United States
Christy
The price is S$239
includes taxes & fees
24 Nov - 25 Nov
Palmer House a Hilton Hotel
A modern hotel with a prominent "Grant Park Hotel" sign and "Best Western" branding.

14. Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
Downtown Chicago
8.2 out of 10, Very good, (2,755 reviews)
"Nice location. Restaurants are just walking distance."
United States
Diojenies Alejandro
The price is S$131
includes taxes & fees
7 Dec - 8 Dec
Best Western Grant Park Hotel
A modern high-rise building with a glass facade, surrounded by other tall buildings.

15. citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,344 reviews)
"Great hotel"
United States
Alban
The price is S$178
includes taxes & fees
23 Nov - 24 Nov
citizenM Chicago Downtown
A restaurant with outdoor seating overlooking a city skyline.

16. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,767 reviews)
"Best stay, wonderful property."
Canada
Bonnie
The price is S$221
includes taxes & fees
15 Dec - 16 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton
A multi-story building with a prominent curved glass facade, surrounded by other high-rise buildings.

17. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (3,025 reviews)
"Great stay!"
United States
Serge
The price is S$225
includes taxes & fees
14 Dec - 15 Dec
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
A large hotel with a classic architectural style, featuring multiple floors and a prominent entrance.

18. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (10,096 reviews)
"Great stay!"
United States
Rafael
The price is S$178
includes taxes & fees
22 Nov - 23 Nov
Congress Plaza Hotel
A rooftop terrace with outdoor seating and a fire pit, overlooking a cityscape with tall buildings.

19. The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,702 reviews)
"Excellent hotel in a great location for everything"
United Kingdom
Andy
The price is S$223
includes taxes & fees
14 Dec - 15 Dec
The Royal Sonesta Chicago Downtown
A Courtyard Marriott hotel with a glass facade, a self-park sign, and a Marriott logo.

20. Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2,082 reviews)
"Hotel location was perfect and the staff was especially helpful with many recommendations for the area! I felt very safe here."
United States
natasha
The price is S$169
includes taxes & fees
6 Dec - 7 Dec
Courtyard by Marriott Chicago Magnificent Mile
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

Chicago and related destinations

Towering skyscrapers frame the stunning Millennium Park where 'The Bean' reflects the city's vibrant energy. Cruise along the Chicago River for spectacular architecture views or catch a Cubs game at historic Wrigley Field.

See all hotels in Chicago
A river with a yellow boat, surrounded by tall buildings and a bridge.

Top reviews in Chicago

A hotel entrance with a marquee sign, a blue carpet, and a flag.
Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago

10/10 Excellent

For the price, great quality in rooms, check in and nearby food options.
Singapore
Rahul
Reviewed March 30, 2024
Hilton Vacation Club Hotel Blake Chicago