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

Chicago Resorts

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Chicago resorts

A large hotel with a central courtyard, a lake, and a bridge.

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, (1,000 reviews)
"excelent , convenient location, nice pool , healthy breakfast options"
United States
Thomas
The price is S$176
includes taxes & fees
4 Dec - 5 Dec
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, (1,004 reviews)
"Clean room and staff were nice"
United States
Monique
The price is S$183
includes taxes & fees
11 Dec - 12 Dec
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, (872 reviews)
"Had a amazing Staycation.. the entire staff is friendly and hotel was clean and well managed"
United States
Jeanette
The price is S$181
includes taxes & fees
1 Dec - 2 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, (1,426 reviews)
"It’s an older hotel with so much charm. We loved our stay."
United States
Jeff
The price is S$209
includes taxes & fees
27 Nov - 28 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, (1,000 reviews)
"Had a blast will return soon!!"
United States
Elegria
The price is S$193
includes taxes & fees
13 Dec - 14 Dec
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.
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Top Chicago Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"I liked that it was downtown in the heart of the city with lots of choices for eating and shopping. I didn’t like that there were no amenities for soft drinks and snacks inside the hotel. It was a nice place overall and I would definitely recommend."
Paula 1-night trip
Posted less than an hour ago
The Chicago Hotel Collection - Magnificent Mile

Find out more about Chicago

Chicago Resorts information

Number of reviews
2,426
Accommodation
5 Resorts
Lowest Price
S$176
Highest Price
S$209

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 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'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. Wind Creek Southland Casino and Hotel - Luxury resort. Enjoy the 8 restaurants, 4 bars and spa. Great Wolf Lodge Illinois - Family-friendly resort. Amenities include 5 restaurants, 6 indoor pools and 2 bars. 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 6 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 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.

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