Search Resorts in Chicago

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Chicago resorts

A spacious, modern interior with large windows offering views of a golf course and a lake.

1. Hilton Chicago/Oak Brook Hills Resort & Conference Center

Hilton Chicago/Oak Brook Hills Resort & Conference Center
4.0 star property
Oak Brook
9.0 out of 10, Wonderful, (1,007 reviews)
"excelent , convenient location, nice pool , healthy breakfast options"
United States
Thomas
The price is 2.932.136 ₫
3.680.862 ₫ total
includes taxes & fees
28 Nov - 29 Nov
Hilton Chicago/Oak Brook Hills Resort & Conference Center
An outdoor dining area with a fire feature, tables, chairs, and red umbrellas.

2. Lincolnshire Marriott Resort

Lincolnshire Marriott Resort
4.0 star property
Half Day
8.8 out of 10, Excellent, (1,000 reviews)
"Clean room and staff were nice"
United States
Monique
The price is 3.472.875 ₫
3.888.926 ₫ total
includes taxes & fees
13 Nov - 14 Nov
Lincolnshire Marriott Resort
A modern spa with a circular hot tub, a sofa, and a view of the city.

3. Wind Creek Chicago Southland Casino and Hotel

Wind Creek Chicago Southland Casino and Hotel
4.5 star property
East Hazel Crest
9.4 out of 10, Exceptional, (850 reviews)
"Had a amazing Staycation.. the entire staff is friendly and hotel was clean and well managed"
United States
Jeanette
The price is 3.873.574 ₫
4.337.548 ₫ total
includes taxes & fees
6 Dec - 7 Dec
Wind Creek Chicago Southland Casino and Hotel
A patio area with outdoor seating, a fire pit, and a view of a golf course.

4. Eaglewood Resort and Spa

Eaglewood Resort and Spa
4.0 star property
Itasca
8.8 out of 10, Excellent, (1,407 reviews)
"Stayed two nights, offered good food and music and a superb room with a view of the golf course."
United States
Jake
The price is 3.260.644 ₫
4.184.612 ₫ total
includes taxes & fees
20 Nov - 21 Nov
Eaglewood Resort and Spa
A spacious lobby with a stone fireplace, multiple seating areas, and large windows offering views of the outdoors.

5. Great Wolf Lodge Illinois

Great Wolf Lodge Illinois
3.0 star property
Gurnee
8.4 out of 10, Very good, (1,002 reviews)
"Had a blast will return soon!!"
United States
Elegria
The price is 3.389.269 ₫
3.863.088 ₫ total
includes taxes & fees
19 Nov - 20 Nov
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.
View all properties

Chicago and related destinations

Towering skyscrapers frame the stunning Millennium Park where 'The Bean' reflects the city's vibrant energy. Cruise along the Chicago River for spectacular architecture views or catch a Cubs game at historic Wrigley Field.

See all hotels in Chicago
A river with a yellow boat, surrounded by tall buildings and a bridge.

Top reviews in Chicago

A modern spa with a circular hot tub, a sofa, and a view of the city.
Wind Creek Chicago Southland Casino and Hotel

Wind Creek Chicago Southland Casino and Hotel

Wind Creek Chicago Southland Casino and Hotel
East Hazel Crest

10/10 Excellent

We stayed here just one night on route up from Nashville toward a road-trip around Lake Michigan. It was cost-effective and a good location but it was a very pleasant surprise. We didn't get a chance to use the casino but the room was exceptional - it felt brand new, all the amenities were great and the bed wonderfully comfortable - would thoroughly recommend if you aren't looking to stay in the centre and need somewhere south of the city
United Kingdom
Kevin
Reviewed July 2, 2026
Wind Creek Chicago Southland Casino and Hotel

Frequently Asked Questions

How many hotel resorts are there in Chicago?

Choose from Expedia's 6 resort hotels in Chicago, where you'll find fun for all the family, beautiful guest rooms and more.

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 6 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 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 Soldier Field 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.