Search Hotels with Pool in Chicago

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Check availability on Chicago Hotels with Pool

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Top Chicago Hotels with 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, (2955)
"Great location and great staff!!"
United States
lynne
The price is ฿2,649
฿3,109 total
includes taxes & fees
22 Dec - 23 Dec
Aloft Chicago Mag Mile
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, (2182)
"Nice Hotel"
United States
Alan
The price is ฿2,852
฿3,348 total
includes taxes & fees
16 Dec - 17 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2122)
"Loved and enjoyed our stay"
United States
Luis
The price is ฿3,271
฿4,637 total
includes taxes & fees
28 Dec - 29 Dec
Palmer House a Hilton Hotel
Indoor pool
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2747)
"Great food clean room friendly staff"
United States
MARINA
The price is ฿2,655
฿4,053 total
includes taxes & fees
6 Jan - 7 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Indoor pool
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
Downtown Chicago
8.4 out of 10, Very good, (4232)
"Staff were amazing."
United States
Debra
The price is ฿2,617
฿3,072 total
includes taxes & fees
18 Dec - 19 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
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, (3444)
"Great hotel"
United States
Clara
The price is ฿3,702
฿4,345 total
includes taxes & fees
22 Dec - 23 Dec
voco Chicago Downtown - Riverwalk by IHG
Indoor pool
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1047)
"Great Hotel!"
United States
Wendy
The price is ฿3,119
฿4,598 total
includes taxes & fees
1 Jan - 2 Jan 2026
Hyatt Centric Chicago Magnificent Mile
Indoor pool
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2033)
"Great hotel."
United States
Mario
The price is ฿3,127
฿3,671 total
includes taxes & fees
22 Dec - 23 Dec
Holiday Inn Chicago Dwtn - The Mart by IHG
Indoor pool
The Wade

The Wade

4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1509)
"Great location, walkable to so many area attractions. Would definitely stay here again. "
United States
Debbie
The price is ฿3,223
฿3,783 total
includes taxes & fees
14 Dec - 15 Dec
The Wade
Pool
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1742)
"Staff was courteous, room was clean, convenient location for us. Price was good as well."
United States
Jamie
The price is ฿2,272
฿2,667 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Garden Inn Chicago Downtown South Loop
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 Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Very nice hotel stay. Would definitely go back "
Rahul 6-night trip
Posted 12 hours ago
The Whitehall Hotel, BW Premier Collection

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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 109 places to stay with pools. While you're visiting, you can explore attractions such as Michigan Avenue and Wrigley Field, 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. Homewood Suites by Hilton Chicago Downtown South Loop: Hotel, 2-minute walk from State Street. Offers a snack bar/deli, a pool and buffet. Hilton Garden Inn Chicago Downtown South Loop: Hotel, 1-minute walk from State Street. Provides a snack bar/deli, a pool and complimentary wireless Internet access. Hyatt Centric Chicago Magnificent Mile: Hotel, 2-minute walk from Michigan Avenue. Features complimentary wireless Internet access, an indoor pool and a 24-hour fitness centre. Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG: Hotel, 4-minute walk from Donald E. Stephens Convention Center. Offers 3 restaurants, an indoor pool and complimentary wireless Internet access.
How many hotels with pools should I expect to find in Chicago?
Expedia's 109 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, Wrigley Field and Naval Base Great Lakes while you're in Chicago. Surround yourself with nature at Millennium Park and Lake Michigan. 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.