Chicago Resorts

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Check prices for these dates

Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
In one month
23 Jan - 25 Jan
In two months
20 Feb - 22 Feb

Our top choices for Chicago resorts

Front of property – evening/night
Hilton Chicago/Oak Brook Hills Resort & Conference Center

Hilton Chicago/Oak Brook Hills Resort & Conference Center

Hilton Chicago/Oak Brook Hills Resort & Conference Center
4.0 star property
Oak Brook
8.8 out of 10, Excellent, (1006)
"Great place "
United States
Ana
The price is S$164
includes taxes & fees
28 Dec - 29 Dec
Hilton Chicago/Oak Brook Hills Resort & Conference Center
Front of property – evening/night
Eaglewood Resort and Spa

Eaglewood Resort and Spa

Eaglewood Resort and Spa
4.0 star property
Itasca
8.8 out of 10, Excellent, (1008)
"Clean hotel, very friendly staff "
United States
Sherelle
The price is S$191
includes taxes & fees
1 Jan - 2 Jan, 2026
Eaglewood Resort and Spa
Banquet hall
Lincolnshire Marriott Resort

Lincolnshire Marriott Resort

Lincolnshire Marriott Resort
4.0 star property
Half Day
8.8 out of 10, Excellent, (1000)
"Great place to stay. "
United States
Aroop
The price is S$170
includes taxes & fees
9 Jan - 10 Jan, 2026
Lincolnshire Marriott Resort
Children’s area
Great Wolf Lodge Illinois

Great Wolf Lodge Illinois

Great Wolf Lodge Illinois
3.0 star property
Gurnee
8.6 out of 10, Excellent, (1000)
"Clean room and friendly staff, great food!"
United States
Patrick
The price is S$197
includes taxes & fees
22 Jan - 23 Jan, 2026
Great Wolf Lodge Illinois
Couples treatment room(s), sauna, body treatments, aromatherapy
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel
4.0 star property
East Hazel Crest
9.4 out of 10, Exceptional, (210)
"Nice size rooms, staff was polite and very helpful"
United States
WILLIAM
The price is S$222
includes taxes & fees
29 Dec - 30 Dec
Wind Creek Southland Casino and 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.
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Top Chicago 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

Find out more about Chicago

Chicago Resorts information

Number of reviews
4,223
Accommodation
5 Resorts
Lowest Price
S$164
Highest Price
S$222

Frequently asked questions

What is Chicago like for a resort holiday?
Dreaming of a relaxing getaway? You deserve the comforts and luxuries of a resort, where you can find everything you need for your trip—from tasty food and drink options to activities and shopping. Pick from 27 resorts in Chicago and discover the right one for you, whether you picture yourself kicking back in a luxury suite or exploring the on-site boutiques.
What's a top resort in Chicago?
Hilton Chicago/Oak Brook Hills Resort & Conference Center - Spa resort. Features 4 restaurants, 2 bars and a golf course. Highly rated for its pool. Eaglewood Resort and Spa - Spa resort. Has 2 restaurants, 2 bars and a golf course. Wind Creek Southland Casino and Hotel - Spa resort. Enjoy the 4 restaurants, 3 bars and spa. Great Wolf Lodge Illinois - Family-friendly resort. Amenities include 5 restaurants, 6 indoor pools and 2 bars. Lincolnshire Marriott Resort - Golf resort. Access to 2 restaurants, 2 bars and a golf course.
How many hotel resorts are there in Chicago?
Choose from Expedia's 27 resort hotels in Chicago, where you'll find fun for all the family, beautiful guest rooms and more.
What can I do in Chicago?
Travellers come to Chicago to experience its theatres, museums and other cultural offerings. Explore the interesting exhibits at Fine Arts Building and Art Institute of Chicago, or catch the latest production at CIBC Theatre or Symphony Center. Other top attractions you can add to your list are Michigan Avenue and Wrigley Field.
What's the seasonal weather in Chicago?
The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Chicago is 1260 mm.
What's the best way to get to and around Chicago?
Fly into Chicago Midway Airport (MDW), which is located 8.6 mi (13.9 km) away. Otherwise, you can search for flights to Chicago O'Hare International Airport (ORD), which is 15.7 mi (25.3 km) away. Nearby metro stations include Monroe Station (Red Line), Monroe Station (Blue Line) and Adams-Wabash Station.

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