Book a Chicago Resort

    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
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Resort in Chicago

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)
"Will stay here again! "
The price is NZ$255
includes taxes & fees
25 Aug - 26 Aug
Hilton Chicago/Oak Brook Hills Resort & Conference Center
Eaglewood Resort and Spa
Front of property - evening/night

Eaglewood Resort and Spa

4.0 star property
8.6 out of 10, Excellent, (1001)
"Perfect for a night layover from o’hare airport. "
The price is NZ$298
includes taxes & fees
17 Aug - 18 Aug
Eaglewood Resort and Spa
Great Wolf Lodge Illinois
Children's area

Great Wolf Lodge Illinois

3.0 star property
8.6 out of 10, Excellent, (1000)
"Great place for family fun"
The price is NZ$360
includes taxes & fees
26 Aug - 27 Aug
Great Wolf Lodge Illinois
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, (83)
"Nice hotel for the area."
The price is NZ$373
includes taxes & fees
26 Aug - 27 Aug
Wind Creek Southland Casino and Hotel
Lincolnshire Marriott Resort
Banquet hall

Lincolnshire Marriott Resort

4.0 star property
8.8 out of 10, Excellent, (993)
"We had a great stay! The staff and food were wonderful! "
The price is NZ$272
includes taxes & fees
5 Sept - 6 Sept
Lincolnshire Marriott Resort
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

Top Chicago Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Me and my wife stood for a little getaway and celebration of our anniversary. This hotel and staff is wonderful great attitude cleanliness was beautiful. Food was great. We had sushi from one restaurant for dinner and then the next morning we had a breakfast buffet in the main restaurant. The food was delicious. Hotel was very clean and staff was great thank you.Hyatt"
Roberto 1-night trip
Posted 19 hours ago
Hyatt Regency Chicago

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?
Hilton Chicago/Oak Brook Hills Resort & Conference Center - Spa resort. Features 4 restaurants, 2 bars and a golf course. Highly rated for its pool. Eaglewood Resort and Spa - Spa resort. Has 2 restaurants, 2 bars and a golf course. Great Wolf Lodge Illinois - Family-friendly resort. Enjoy the 5 restaurants, 6 indoor pools and 2 bars. 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.