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Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Featured Resorts in Chicago

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, (1000)
"Will stay here again! "
The price is P7,073
P8,817 total
includes taxes & fees
Aug 25 - Aug 26
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, (1003)
"Rented a two bedroom suite and it was absolutely perfect for 6 people. We love coming here for a one or two day quick trip. "
The price is P10,993
P12,530 total
includes taxes & fees
Aug 27 - Aug 28
Great Wolf Lodge Illinois
Eaglewood Resort and Spa
Guests arrive at the hotel's entrance, where a covered walkway leads to the main building.

Eaglewood Resort and Spa

4.0 star property
8.6 out of 10, Excellent, (1004)
"It was really nice could use more food options and a dj on Saturday nights "
The price is P8,224
P10,294 total
includes taxes & fees
Aug 12 - Aug 13
Eaglewood Resort and Spa
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, (985)
"We had a great stay! The staff and food were wonderful! "
The price is P7,561
P8,467 total
includes taxes & fees
Aug 15 - Aug 16
Lincolnshire Marriott Resort
Wind Creek Southland Casino and Hotel
Couples treatment rooms, sauna, body treatments, aromatherapy

Wind Creek Southland Casino and Hotel

4.0 star property
9.4 out of 10, Exceptional, (70)
"Nice hotel for the area."
The price is P11,575
P12,961 total
includes taxes & fees
Sep 1 - Sep 2
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.
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Top Chicago Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Great location, staff and view! "
Kimberley 1-night trip
Posted 13 hours ago
Hyatt Regency Chicago

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 42 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?
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 will I find in Chicago?
Choose among Expedia's 42 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 Michigan Avenue 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.