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Check prices for these dates

Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec
In one month
19 Dec - 21 Dec
In two months
16 Jan - 18 Jan

Browse Select Chicago Resorts

Front of property – evening/night
Eaglewood Resort and Spa

Eaglewood Resort and Spa

4.0 star property
Itasca
8.8 out of 10, Excellent, (1006)
"Perfect, Thanks for a great stay!"
United States
William
The price is ฿2,296
฿3,263 total
includes taxes & fees
7 Dec - 8 Dec
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

4.0 star property
Oak Brook
8.8 out of 10, Excellent, (1005)
"Excellent restaurant!"
United States
William Dino
The price is ฿3,005
฿3,873 total
includes taxes & fees
15 Dec - 16 Dec
Hilton Chicago/Oak Brook Hills Resort & Conference Center
Banquet hall
Lincolnshire Marriott Resort

Lincolnshire Marriott Resort

4.0 star property
Half Day
8.8 out of 10, Excellent, (1002)
"Room was nice, food delicious and employees friendly!"
United States
Jim
The price is ฿3,833
฿4,292 total
includes taxes & fees
19 Dec - 20 Dec
Lincolnshire Marriott Resort
Children’s area
Great Wolf Lodge Illinois

Great Wolf Lodge Illinois

3.0 star property
Gurnee
8.6 out of 10, Excellent, (1002)
"Amazing place kids loved it will be back soon. Thank you. "
United States
Luis
The price is ฿4,355
฿4,964 total
includes taxes & fees
17 Dec - 18 Dec
Great Wolf Lodge Illinois
Couples treatment room(s), sauna, body treatments, aromatherapy
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, (167)
"Beautiful place to stay "
United States
Floyd
The price is ฿4,070
฿4,557 total
includes taxes & fees
23 Nov - 24 Nov
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/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Room was spacious and clean. Staff were very friendly and helpful. "
Kristina Marie 2-night trip
Posted 9 hours ago
Hilton Chicago/Magnificent Mile Suites

Find out more about Chicago

Chicago Resorts information

Number of reviews
3,170
Accommodation
5 Resorts
Lowest Price
฿3,263
Highest Price
฿4,557

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 Navy Pier.
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.