A river with a yellow boat, surrounded by tall buildings and a bridge.

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
11 Sep - 13 Sep
In two weeks
18 Sep - 20 Sep
In one month
2 Oct - 4 Oct
In two months
30 Oct - 1 Nov

Our top choices for Chicago resorts

Golf

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, (1,008 reviews)
"Very nice weekend escape convenient to where we were going"
United States
chauncey
The price is AED 494
AED 609 total
includes taxes & fees
7 Sep - 8 Sep
Hilton Chicago/Oak Brook Hills Resort & Conference Center
Exterior

2. Eaglewood Resort and Spa

Eaglewood Resort and Spa
4.0 star property
Itasca
8.8 out of 10, Excellent, (1,307 reviews)
"Wonderful place"
United States
Brandon
The price is AED 463
AED 594 total
includes taxes & fees
6 Sep - 7 Sep
Eaglewood Resort and Spa
Couples treatment rooms, sauna, body treatments, aromatherapy

3. Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel
4.5 star property
East Hazel Crest
9.4 out of 10, Exceptional, (657 reviews)
"The hotel was very nice and had great amenities, offered a great buffet on Sundays"
United States
Kierra
The price is AED 616
AED 690 total
includes taxes & fees
2 Sep - 3 Sep
Wind Creek Southland Casino and Hotel
Lobby

4. Great Wolf Lodge Illinois

Great Wolf Lodge Illinois
3.0 star property
Gurnee
8.6 out of 10, Excellent, (1,009 reviews)
"The location to the Navy Graduation was great. Plenty of stuff to do. The climbing wall and bowling were a lot of fun."
United States
Zachariah
The price is AED 569
AED 649 total
includes taxes & fees
2 Sep - 3 Sep
Great Wolf Lodge Illinois
Property amenity

5. Lincolnshire Marriott Resort

Lincolnshire Marriott Resort
4.0 star property
Half Day
8.8 out of 10, Excellent, (1,002 reviews)
"Rooms are updated and hotel was updated, food was very good."
United States
Cheryl
The price is AED 558
AED 625 total
includes taxes & fees
11 Sep - 12 Sep
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.
View all properties
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

The Wade

The Wade

8/10 Good
"Our stay at The Wade on August 22, 2026 was 2rd time for our family, and we had one city-view room and 2 lake-view rooms. The Wade has great location, beautiful view, and clear rooms. I gave it a rating of 4 this time because I simply could not accept the service for the following reasons. 1. We checked in after 4pm, the hotel's official check-in time is 4pm, yet we were initially given only one room. We got the 2rd room around 5:30pm, and the last one after 10pm. 2. The elevator system was too bad so we had to wait too long for it every time. 3. Around 1:00 PM on 8/13, I was queuing to pick up our stored luggages. There are many customers were waiting for the service. When it was my turn, the front desk staff ignored me and instead attended to a customer who had been standing by side and was not in line. I objected, but the staff claimed falsely that customer arrived before us, even though that customer had definitely arrived after us. Standing nearby, my son was very angry and said: "Let's never stay at this hotel again.!""
LISA YING 1-night trip
Posted less than an hour ago
The Wade

Frequently asked questions

What is Chicago like for a resort vacation?
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. Check out the 5 resorts in Chicago and discover the one that's best for you, whether you picture yourself kicking back in a luxury suite or hitting the golf course for an afternoon game.
What's a top resort in Chicago?
Eaglewood Resort and Spa - Spa resort. Features 2 restaurants, 2 bars, and a golf course. Wind Creek Southland Casino and Hotel - Luxury resort. Has 8 restaurants, 4 bars, and a full-service spa. Great Wolf Lodge Illinois - Family-friendly resort. Enjoy the 5 restaurants, 6 indoor pools, and 2 bars. Hilton Chicago/Oak Brook Hills Resort & Conference Center - Spa resort. Amenities include 4 restaurants, 2 bars, and a golf course. Highly rated for its pool. Lincolnshire Marriott Resort - Golf resort. Access to 2 restaurants, 2 bars, and a golf course.
How many hotel resorts will I find in Chicago?
Choose among Expedia's 5 resort hotels in Chicago where you'll find top-notch bars, spacious rooms, and more.
What can I do in Chicago?
Travelers come to Chicago to experience its theaters, museums, and other cultural offerings. Check out 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 weather like in Chicago?
The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 31°F. Average annual precipitation for Chicago is 50 inches.
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. You can also search for flights into Chicago O'Hare Intl. Airport (ORD), which is 15.7 mi (25.3 km) away. You can walk to nearby metro stations including Monroe Station (Red Line), Monroe Station (Blue Line), and Adams-Wabash Station.

Explore a world of travel with Expedia