Chicago Resorts

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Check prices for these dates

Next weekend
5 Sept - 7 Sept
In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct

Featured Resorts in Chicago

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

Hilton Chicago/Oak Brook Hills Resort & Conference Center

4.0 star property
8.6 out of 10, Excellent, (1006)
"Will stay here again! "
The price is S$194
includes taxes & fees
14 Sept - 15 Sept
Hilton Chicago/Oak Brook Hills Resort & Conference Center
Eaglewood Resort and Spa
Front of property – evening/night

Eaglewood Resort and Spa

4.0 star property
8.6 out of 10, Excellent, (1011)
"Very nice and reasonably priced hotel."
The price is S$173
includes taxes & fees
31 Aug - 1 Sept
Eaglewood Resort and Spa
Lincolnshire Marriott Resort
Banquet hall

Lincolnshire Marriott Resort

4.0 star property
8.8 out of 10, Excellent, (998)
"We had a great stay! The staff and food were wonderful! "
The price is S$207
includes taxes & fees
12 Sept - 13 Sept
Lincolnshire Marriott Resort
Wind Creek Southland Casino and Hotel
Couples treatment room(s), sauna, body treatments, aromatherapy

Wind Creek Southland Casino and Hotel

4.0 star property
9.2 out of 10, Wonderful, (94)
"Great place "
The price is S$286
includes taxes & fees
28 Aug - 29 Aug
Wind Creek Southland Casino and Hotel
Great Wolf Lodge Illinois
Children’s area

Great Wolf Lodge Illinois

3.0 star property
8.6 out of 10, Excellent, (1004)
"First time there and we loved it "
The price is S$277
includes taxes & fees
2 Sept - 3 Sept
Great Wolf Lodge Illinois
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

Find out more about Chicago

Find out more about Chicago

Chicago Resorts information

Number of reviews
4,099
Accommodation
5 Resorts
Lowest Price
S$173
Highest Price
S$286

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 36 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. Great Wolf Lodge Illinois - Family-friendly resort. Enjoy the 5 restaurants, 6 indoor pools and 2 bars. Wind Creek Southland Casino and Hotel - Spa resort. Amenities include 4 restaurants, 3 bars and a full-service spa. 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 36 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.