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Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Browse Select Chicago Resorts

Eaglewood Resort and Spa
Front of property – evening/night

Eaglewood Resort and Spa

4.0 star property
8.8 out of 10, Excellent, (1001)
"Property was clean, quiet, and great place to stay."
The price is ฿3,098
฿4,150 total
includes taxes & fees
5 Oct - 6 Oct
Eaglewood Resort and Spa
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, (1002)
"Awesome "resort" property."
The price is ฿3,618
฿4,552 total
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago/Oak Brook Hills Resort & Conference Center
Wind Creek Southland Casino and Hotel
Couples treatment room(s), sauna, body treatments, aromatherapy

Wind Creek Southland Casino and Hotel

4.0 star property
9.4 out of 10, Exceptional, (131)
"Amazing hotel "
The price is ฿5,793
฿6,487 total
includes taxes & fees
19 Oct - 20 Oct
Wind Creek Southland Casino and Hotel
Lincolnshire Marriott Resort
Banquet hall

Lincolnshire Marriott Resort

4.0 star property
8.8 out of 10, Excellent, (1001)
"We had a great stay! The staff and food were wonderful! "
The price is ฿4,657
฿5,215 total
includes taxes & fees
31 Oct - 1 Nov
Lincolnshire Marriott Resort
Great Wolf Lodge Illinois
Children’s area

Great Wolf Lodge Illinois

3.0 star property
8.6 out of 10, Excellent, (1002)
"We had a great stay staff was very friendly and helpful! We had a blast while there only complaint would be the breakfast it was buffet style but food was cold. "
The price is ฿4,819
฿5,493 total
includes taxes & fees
14 Oct - 15 Oct
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

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"Very comfortable stay, excellent location. "
Andrea 3-night trip
Posted 18 hours ago
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Find out more about Chicago

Find out more about Chicago

Chicago Resorts information

Number of reviews
3,210
Accommodation
5 Resorts
Lowest Price
฿4,150
Highest Price
฿6,487

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 37 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?
Eaglewood Resort and Spa - Spa resort. Features 2 restaurants, 2 bars and a golf course. Hilton Chicago/Oak Brook Hills Resort & Conference Center - Spa resort. Has 4 restaurants, 2 bars and a golf course. Highly rated for its pool. Wind Creek Southland Casino and Hotel - Spa resort. Enjoy the 4 restaurants, 3 bars and spa. Lincolnshire Marriott Resort - Golf resort. Amenities include 2 restaurants, 2 bars and a golf course. Great Wolf Lodge Illinois - Family-friendly resort. Access to 5 restaurants, 6 indoor pools and 2 bars.
How many hotel resorts are there in Chicago?
Choose from Expedia's 37 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.