Book a Chicago Resort

Most properties are fully refundable. Because flexibility matters.

Save an average of 15% on thousands of hotels with Expedia Rewards.

Search over 2.9 million properties and 550 airlines worldwide

Find properties with these dates

Tonight
May 12 - May 13
Tomorrow
May 13 - May 14
Next weekend
May 17 - May 19

Compare Resorts in Chicago with updated reviews, rates, and availability.

Lincolnshire Marriott Resort
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers
Lincolnshire Marriott Resort
4.0 star property
8.8 out of 10, Excellent, (846)
"Old property, but in reasonable shape with comfortable room."
The price is ￥24,769
per night
Jun 7 - Jun 8
Lincolnshire Marriott Resort
Great Wolf Lodge Illinois
Children's area
Great Wolf Lodge Illinois
3.0 star property
8.6 out of 10, Excellent, (701)
"Great place for kids and family."
The price is ￥23,211
per night
May 16 - May 17
Great Wolf Lodge Illinois
Eaglewood Resort and Spa
Front of property - evening/night
Eaglewood Resort and Spa
4.0 star property
8.4 out of 10, Very Good, (1003)
"Bath tubs needs slip proof strips or mats non slip treatment etc."
The price is ￥21,653
per night
May 19 - May 20
Eaglewood Resort and Spa
Don't see what you're looking for?
See all available properties in Chicago
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.

Other property types in Chicago

Sentral Michigan Avenue
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (395)
"It was amazing to have a whole apartment for the price of a hotel room... less actually. Their system is simple and painless. I will book here again!"
The price is ￥22,292
per night
May 27 - May 28
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (221)
"Nice location and nice property. We enjoyed our visit there."
Kasa Magnificent Mile Chicago
Sonder South Wabash
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (295)
"Overall the stay was amazing. We will definitely be booking here again."
The price is ￥30,230
per night
May 28 - May 29
Sonder South Wabash
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.

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 5 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?
Eaglewood Resort and Spa - Spa resort. Features 2 restaurants, 2 bars, and a golf course. Great Wolf Lodge Illinois - Family-friendly resort. Has 5 restaurants, 6 indoor pools, and 2 bars. Lincolnshire Marriott Resort - Golf resort. Enjoy the 2 restaurants, 2 bars, and golf course.
How many hotel resorts will I find in Chicago?
Choose among Expedia’s 5 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 Art Institute of Chicago and Field Museum of Natural History, or catch the latest production at CIBC Theatre or Symphony Center. Other top attractions you can add to your list are Grant Park and Navy Pier.
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.