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Search Hotels with Swimming Pool in Hillside

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Check availability on Hillside Hotels with Swimming Pool

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

Top Hillside Hotels with Swimming Pool

Indoor pool
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

2.5 star property
Hillside
7.0 out of 10, Good, (1008)
"Nice place to stay"
United States
Roque
The price is ₹8,369
₹9,372 total
includes taxes & fees
28 Dec - 29 Dec
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
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 ₹6,407
₹7,522 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Garden Inn Chicago Downtown South Loop
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, (3446)
"Great hotel"
United States
Clara
The price is ₹10,439
₹12,254 total
includes taxes & fees
22 Dec - 23 Dec
voco Chicago Downtown - Riverwalk by IHG
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, (2956)
"Great location and great staff!!"
United States
lynne
The price is ₹7,469
₹8,768 total
includes taxes & fees
22 Dec - 23 Dec
Aloft Chicago Mag Mile
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 ₹7,559
₹11,515 total
includes taxes & fees
6 Jan - 7 Jan 2026
Embassy Suites by Hilton Chicago Downtown 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, (2034)
"Great hotel."
United States
Mario
The price is ₹8,819
₹10,353 total
includes taxes & fees
22 Dec - 23 Dec
Holiday Inn Chicago Dwtn - The Mart by IHG
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, (2184)
"Nice Hotel"
United States
Alan
The price is ₹8,044
₹9,442 total
includes taxes & fees
16 Dec - 17 Dec
DoubleTree by Hilton Chicago - Magnificent 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 ₹8,797
₹12,968 total
includes taxes & fees
1 Jan - 2 Jan 2026
Hyatt Centric Chicago Magnificent Mile
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 ₹9,089
₹10,670 total
includes taxes & fees
14 Dec - 15 Dec
The Wade
Indoor pool
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2306)
"Great place - stayed with extended family. Lounge areas and amenities met everyone’s needs "
United States
Elizabeth
The price is ₹9,269
₹13,761 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Royal Sonesta Chicago River North
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 Hillside 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 17 hours ago
The Whitehall Hotel, BW Premier Collection

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Frequently asked questions

What are some accommodation options with pools in Hillside?
Palmer House a Hilton Hotel: Hotel steps from State Street. Features a full-service spa, an indoor pool and a 24-hour fitness centre. 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. Features 2 restaurants, an indoor pool and a sauna. Congress Plaza Hotel: Hotel, 4-minute walk from State Street. Features 2 restaurants, an indoor pool and a health club.
What is there to see and do in Hillside?
Explore places such as Wrigley Field, Michigan Avenue and United Center while you're in the area. Take a walk along the waterfront at North Avenue Beach and Oak Street Beach. Travellers love Hillside for its array of dining options.
When is the best time to book a hotel with a pool in Hillside?
You may want to consider a place to stay with an outdoor swimming pool if you'll be visiting Hillside in the hottest months of July, August or June, when the average temperature is 22°C. Accommodation with an indoor pool may be the way to go if you are visiting during the coldest months of January, February or December, when the average temperature is -1°C.