Chicago Resorts

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Check prices for these dates

Next weekend
11 Jul - 13 Jul
In two weeks
18 Jul - 20 Jul
In one month
1 Aug - 3 Aug
In two months
29 Aug - 31 Aug

Featured Resorts in Chicago

Eaglewood Resort and Spa
Front of property – evening/night

Eaglewood Resort and Spa

4.0 star property
8.6 out of 10, Excellent, (1003)
"Great location "
The price is S$205
includes taxes & fees
7 Jul - 8 Jul
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, (1001)
"Liked the proximity to our family who live in the area. Liked that there is both in- and out- pools."
The price is S$193
includes taxes & fees
27 Jul - 28 Jul
Hilton Chicago/Oak Brook Hills Resort & Conference Center
Great Wolf Lodge Illinois
Children’s area

Great Wolf Lodge Illinois

3.0 star property
8.6 out of 10, Excellent, (1003)
"This was a first time visit for our family and everything was absolutely fantastic! "
The price is S$289
includes taxes & fees
21 Jul - 22 Jul
Great Wolf Lodge Illinois
Lincolnshire Marriott Resort
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers

Lincolnshire Marriott Resort

4.0 star property
8.8 out of 10, Excellent, (959)
"The out door patio area is really nice."
The price is S$198
includes taxes & fees
13 Jul - 14 Jul
Lincolnshire Marriott Resort
Wind Creek Southland Casino and Hotel
Check-in/check-out kiosk

Wind Creek Southland Casino and Hotel

4.0 star property
9.2 out of 10, Wonderful, (35)
"Great stay lovely rooms"
The price is S$284
includes taxes & fees
8 Jul - 9 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?
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. Great Wolf Lodge Illinois - Family-friendly resort. Enjoy the 5 restaurants, 6 indoor pools and 2 bars. Lincolnshire Marriott Resort - Golf resort. Amenities include 2 restaurants, 2 bars and a golf course. Wind Creek Southland Casino and Hotel - Spa resort. Access to 4 restaurants, 3 bars and a full-service spa.
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 Art Institute of Chicago and Fine Arts Building, or catch the latest production at CIBC Theatre or Symphony Center. Other top attractions you can add to your list are Michigan Avenue and Soldier Field.
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.