Find Hotels with a Pool in Old Town Chicago, IL

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Check availability on Old Town Chicago Hotels with a Pool

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

Top Old Town Chicago Hotels with a Pool

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 SAR 267
SAR 314 total
includes taxes & fees
5 Jan - 6 January 2026
Hilton Garden Inn Chicago Downtown South Loop
Indoor pool, open 5:00 AM to 11:00 PM, sun 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, (3446)
"Great hotel"
United States
Clara
The price is SAR 435
SAR 511 total
includes taxes & fees
21 Dec - 22 Dec
voco Chicago Downtown - Riverwalk by IHG
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, (2123)
"Loved and enjoyed our stay"
United States
Luis
The price is SAR 385
SAR 545 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
8.2 out of 10, Very Good, (2748)
"Great food clean room friendly staff"
United States
MARINA
The price is SAR 312
SAR 477 total
includes taxes & fees
6 Jan - 7 January 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Outdoor 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, (2184)
"Nice Hotel"
United States
Alan
The price is SAR 335
SAR 394 total
includes taxes & fees
16 Dec - 17 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool, open 7:00 AM to 10:00 PM, sun 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 SAR 312
SAR 366 total
includes taxes & fees
22 Dec - 23 Dec
Aloft Chicago Mag Mile
Indoor pool
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1048)
"Great Hotel!"
United States
Wendy
The price is SAR 367
SAR 541 total
includes taxes & fees
1 Jan - 2 January 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 SAR 368
SAR 432 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 SAR 379
SAR 445 total
includes taxes & fees
14 Dec - 15 Dec
The Wade
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, (4233)
"Staff were amazing."
United States
Debra
The price is SAR 308
SAR 361 total
includes taxes & fees
18 Dec - 19 Dec
Hilton Garden Inn Chicago Downtown/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.
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Top Old Town Chicago Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"I always love staying at this place when I visit"
William 1-night trip
Posted 5 hours ago
Hyatt Regency Chicago

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Frequently asked questions

What are some accommodations with pools in Old Town Chicago?
Palmer House a Hilton Hotel: Hotel steps from State Street. Features a full-service spa, an indoor pool, and a 24-hour fitness center. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool, and flat-screen televisions. Hilton Chicago/Magnificent Mile Suites: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a sauna. Congress Plaza Hotel: Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool, and a health club.
What is there to see and do in Old Town Chicago?
While you're in the area, consider exploring places like Michigan Avenue, Wrigley Field, and Navy Pier. Make a point to visit attractions like North Avenue Beach and Lincoln Park Zoo. Old Town Chicago appeals to visitors with its beautiful lakeside setting, bar scene, and array of dining options.
When is the best time to book a hotel with a pool in Old Town Chicago?
You may want to consider a place to stay that offers an outdoor if you plan to visit in the hottest months of July, August, or June when the average temp is 70°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 31°F.