Chicago Resorts

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Check prices for these dates

Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul
In one month
8 Aug - 10 Aug
In two months
5 Sept - 7 Sept

Featured Resorts in Chicago

Hilton Chicago/Oak Brook Hills Resort & Conference Center
Experience the grandeur of this iconic hotel, set amidst beautifully landscaped gardens.

Hilton Chicago/Oak Brook Hills Resort & Conference Center

4.0 star property
8.6 out of 10, Excellent, (1010)
"We’ve stayed here several times and always enjoy ourselves."
The price is S$194
includes taxes & fees
10 Aug - 11 Aug
Hilton Chicago/Oak Brook Hills Resort & Conference Center
Great Wolf Lodge Illinois
Explore a forest-inspired play area with a wooden play structure, rope bridge, slide, and climbing elements on a lush artificial turf surface.

Great Wolf Lodge Illinois

3.0 star property
8.6 out of 10, Excellent, (1006)
"This was a first time visit for our family and everything was absolutely fantastic! "
The price is S$320
includes taxes & fees
22 Jul - 23 Jul
Great Wolf Lodge Illinois
Eaglewood Resort and Spa
Guests arrive at the hotel's entrance, where a covered walkway leads to the main building.

Eaglewood Resort and Spa

4.0 star property
8.6 out of 10, Excellent, (1017)
"Excellent place and service"
The price is S$232
includes taxes & fees
20 Jul - 21 Jul
Eaglewood Resort and Spa
Lincolnshire Marriott Resort
Experience the serene ambiance of this beautifully designed space, featuring a central aisle, floral arrangements, and intricate wall designs.

Lincolnshire Marriott Resort

4.0 star property
8.8 out of 10, Excellent, (968)
"The out door patio area is really nice."
The price is S$199
includes taxes & fees
20 Jul - 21 Jul
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
9.4 out of 10, Exceptional, (38)
"Great stay lovely rooms"
The price is S$285
includes taxes & fees
14 Jul - 15 Jul
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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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 42 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?
Great Wolf Lodge Illinois - Family-friendly resort. Features 5 restaurants, 6 indoor pools and 2 bars. Hilton Chicago/Oak Brook Hills Resort & Conference Center - Spa resort. Has 4 restaurants, 2 bars and a golf course. Highly rated for its pool. Eaglewood Resort and Spa - Spa resort. Enjoy the 2 restaurants, 2 bars and golf course. 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 42 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.