Search Resorts in Chicago

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Browse Select Chicago Resorts

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, (1004)
"Will stay here again! "
The price is Rp1.984.056
Rp2.473.351 total
includes taxes & fees
4 Sept - 5 Sept
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, (1001)
"Loved the waterpark, restaurant options and customer service. "
The price is Rp3.092.418
Rp3.524.739 total
includes taxes & fees
4 Sept - 5 Sept
Great Wolf Lodge Illinois
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, (991)
"We had a great stay! The staff and food were wonderful! "
The price is Rp2.278.210
Rp2.551.139 total
includes taxes & fees
24 Aug - 25 Aug
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, (77)
"Nice hotel for the area."
The price is Rp3.256.038
Rp3.646.108 total
includes taxes & fees
20 Aug - 21 Aug
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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.