Hotels with Pool & Resorts in Chicago from NZ$158

  • 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 availability on Chicago Hotels with Pool

Our top choices for Chicago hotels with a pool

Indoor pool, open 7:00 AM to 10:00 PM, pool loungers

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,065 reviews)
"Great location and friendly staff. "
United States
Pablo
The price is NZ$165
includes taxes & fees
22 Feb - 23 Feb
Aloft Chicago Mag Mile
Indoor pool

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,790 reviews)
"Great stay"
United States
Jennifer
The price is NZ$175
includes taxes & fees
18 Feb - 19 Feb
Hilton Chicago/Magnificent Mile Suites
Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,305 reviews)
"Great staff, room spotless, great price."
United States
Robert
The price is NZ$178
includes taxes & fees
18 Feb - 19 Feb
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,667 reviews)
"Lovely room, beautiful hotel, wonderful staff, ideal location to navy pier & Michigan Ave. "
United States
Norah
The price is NZ$173
includes taxes & fees
22 Feb - 23 Feb
The Wade
Indoor pool

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,291 reviews)
"Excellent stay, we loved it "
United States
Melani
The price is NZ$302
includes taxes & fees
21 Feb - 22 Feb
Palmer House a Hilton Hotel
Indoor pool

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2,617 reviews)
"The room was clean and the staff was very friendly."
United States
Andrea
The price is NZ$318
includes taxes & fees
21 Feb - 22 Feb
Hilton Chicago
Indoor pool, open 5:00 AM to 11:00 PM, pool loungers

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3,669 reviews)
"Great place to stay"
United States
suleman
The price is NZ$243
includes taxes & fees
15 Feb - 16 Feb
voco Chicago Downtown - Riverwalk by IHG
Indoor pool

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (4,358 reviews)
"Great staff, great room, and close to everything "
United States
George
The price is NZ$158
includes taxes & fees
18 Feb - 19 Feb
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Indoor pool

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (5,652 reviews)
"Always a great stay, clean, great breakfast, great pool. "
United States
Zachary
The price is NZ$199
includes taxes & fees
22 Feb - 23 Feb
Embassy Suites by Hilton Chicago Downtown River North
Indoor pool

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,078 reviews)
"Amazing location, excellent service and great pool and hot tub. "
United States
Tim
The price is NZ$262
includes taxes & fees
22 Feb - 23 Feb
Hyatt Centric Chicago Magnificent Mile
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

Choose what matters most at hotels with a pool in Chicago

Breakfast included
Spa pool

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Hotels with pools and free breakfast in Chicago

Lobby
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3065)
The price is NZ$165
includes taxes & fees
22 Feb - 23 Feb
Aloft Chicago Mag Mile
View all properties

Hotels with pools and spa pools in Chicago

Exterior
Hilton Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2617)
The price is NZ$318
includes taxes & fees
21 Feb - 22 Feb
Hilton Chicago
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

Top Chicago Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Great location, beautiful historic hotel with clean, updated rooms. "
Jennifer 4-night trip
Posted 1 day ago
Congress Plaza Hotel

Frequently asked questions

What's it like visiting Chicago?
If lounging by a pool is your idea of a great holiday, you might want to think about lively Chicago, which offers 133 places to stay with pools. While you're visiting, you can explore attractions such as Michigan Avenue and United Center, and then kick back and relax poolside at one of the accommodation options in Chicago that guests like for their pools.
What are some hotels with pools in Chicago?
Embassy Suites by Hilton Chicago Downtown River North: Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool and flat-screen televisions. Hilton Garden Inn Chicago Downtown South Loop: Hotel, 1-minute walk from State Street. Offers a snack bar/deli, a pool and complimentary wireless Internet access. Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG: Hotel steps from Rosemont Theatre. Provides 3 restaurants, an indoor pool and complimentary wireless Internet access. The Ritz-Carlton, Chicago: Hotel, 2-minute walk from Michigan Avenue. Features a full-service spa, a pool and Smart televisions. Holiday Inn & Suites Chicago - Downtown by IHG: Hotel, 10-minute walk from Willis Tower. Offers a snack bar/deli, a seasonal outdoor pool and complimentary wireless Internet access.
How many hotels with pools should I expect to find in Chicago?
Expedia's 133 hotels in Chicago give you a great choice for your poolside getaway.
What is there to see and do in Chicago?
Explore places such as Michigan Avenue, United Center and Wrigley Field while you're in Chicago. Surround yourself with nature at Millennium Park and Grant Park. Visitors have positive things to say about the popular theatre scene and stunning architecture in Chicago.
When is the best time to book a hotel with a pool in Chicago?
You may want to think about accommodation with an outdoor swimming pool if you're planning to visit Chicago in the warmest months of July, August or June, when the average temperature is 21°C. Accommodation offering an indoor pool may be what you want if you are visiting during the coldest months of January, February or December, when the average temperature is -1°C.
What's the best way to travel around Chicago?
Knowing the transportation options in Chicago can help you enjoy the area beyond your hotel pool. You can access metro transport at Monroe Station (Red Line), Monroe Station (Blue Line) and Adams-Wabash Station. If you'd like to venture out around the area, you may want to rent a car for your trip.

Explore a world of travel with Expedia