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Check prices for these dates

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

Our top choices for Chicago resorts

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, (1007)
"Clean hotel, very friendly staff "
United States
Sherelle
The price is ₩162,524
₩212,874 total
includes taxes & fees
Dec 28 - Dec 29
Eaglewood Resort and Spa
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, (1005)
"Great place "
United States
Ana
The price is ₩148,163
₩188,943 total
includes taxes & fees
Dec 25 - Dec 26
Hilton Chicago/Oak Brook Hills Resort & Conference Center
Banquet hall
Lincolnshire Marriott Resort

Lincolnshire Marriott Resort

Lincolnshire Marriott Resort
4.0 star property
Half Day
8.8 out of 10, Excellent, (1004)
"Room was nice, food delicious and employees friendly!"
United States
Jim
The price is ₩174,344
₩195,230 total
includes taxes & fees
Jan 9 - Jan 10, 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, (1006)
"Clean room and friendly staff, great food!"
United States
Patrick
The price is ₩198,131
₩225,830 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Great Wolf Lodge Illinois
Couples treatment rooms, 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, (209)
"Nice size rooms, staff was polite and very helpful"
United States
WILLIAM
The price is ₩238,024
₩266,540 total
includes taxes & fees
Dec 23 - Dec 24
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

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Staff very friendly"
Kara 1-night trip
Posted 8 hours ago
Hilton Chicago

Find out more about Chicago

Chicago Resorts information

Number of reviews
4,219
Accommodation
5 Resorts
Lowest Price
₩188,943
Highest Price
₩266,540

Frequently asked questions

What is Chicago like for a resort vacation?
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. Check out the 27 resorts in Chicago and discover the one that's best for you, whether you picture yourself kicking back in a luxury suite or hitting the golf course for an afternoon game.
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 will I find in Chicago?
Choose among Expedia's 27 resort hotels in Chicago where you'll find top-notch bars, spacious rooms, and more.
What can I do in Chicago?
Travelers come to Chicago to experience its theaters, museums, and other cultural offerings. Check out 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 weather like in Chicago?
The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 31°F. Average annual precipitation for Chicago is 50 inches.
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. You can also search for flights into Chicago O'Hare Intl. Airport (ORD), which is 15.7 mi (25.3 km) away. You can walk to nearby metro stations including Monroe Station (Red Line), Monroe Station (Blue Line), and Adams-Wabash Station.