Find Hotels with a Pool in Highland Hills, IL

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Check availability on Highland Hills Hotels with a Pool

Our top choices for Highland Hills hotels with a pool

Indoor pool, open 5:00 AM to 11:00 PM, sun loungers
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3480)
"Very helpful staff, clean rooms and really great breakfast buffet. "
United States
Katherine
The price is NT$3,587
NT$4,211 total
includes taxes & fees
Dec 28 - Dec 29
voco Chicago Downtown - Riverwalk by IHG
Indoor pool
Holiday Inn Chicago Dwtn - The Mart by IHG

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, (2043)
"room was good,location was perfect!"
United States
Kyan
The price is NT$3,338
NT$3,918 total
includes taxes & fees
Jan 7 - 2026/1/8
Holiday Inn Chicago Dwtn - The Mart by IHG
Indoor pool
Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1127)
"Clean and large rooms, very friendly and helpful staff!"
United States
Kayla
The price is NT$3,431
NT$4,028 total
includes taxes & fees
Dec 25 - Dec 26
Hyatt Place Chicago/Downtown - The Loop
Seasonal outdoor pool
The Hoxton Chicago

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1008)
"Awesome hotel"
United States
Eligija
The Hoxton Chicago
Indoor pool, sun loungers
Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1003)
"Good service & nice clean rooms "
United States
Yessica
The price is NT$3,718
NT$4,365 total
includes taxes & fees
Jan 11 - 2026/1/12
Hampton Inn Chicago West Loop Fulton Market Area
Indoor pool
Hyatt House Chicago West Loop

Hyatt House Chicago West Loop

Hyatt House Chicago West Loop
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1131)
"I always come back to this Hotel everything is close the area is full of things to do really love staying here !!"
United States
Sandra
The price is NT$4,211
NT$4,944 total
includes taxes & fees
Dec 28 - Dec 29
Hyatt House Chicago West Loop
Indoor pool
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC
2.5 star property
Near West Side
9.6 out of 10, Exceptional, (368)
"Beautiful rooms, great breakfast and amazing customer service! "
United States
Keana
The price is NT$2,720
NT$3,193 total
includes taxes & fees
Dec 28 - Dec 29
Hampton Inn & Suites Chicago Medical District UIC
Indoor pool, sun loungers
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1004)
"Good place to stay in."
United States
Joan
The price is NT$3,968
NT$4,658 total
includes taxes & fees
Dec 27 - Dec 28
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
Outdoor spa tub
Level Chicago - River North

Level Chicago - River North

Level Chicago - River North
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (795)
"Kitchen and laundry in room, staff was very friendly and helpful."
United States
Tiffany
The price is NT$5,357
NT$6,984 total
includes taxes & fees
Dec 17 - Dec 18
Level Chicago - River North
Indoor pool
Country inn & Suites by Radisson Bolingbrook, I-55

Country inn & Suites by Radisson Bolingbrook, I-55

Country inn & Suites by Radisson Bolingbrook, I-55
3.0 star property
Bolingbrook
9.2 out of 10, Wonderful, (376)
"Staff was very friendly. I loved the fact that they had delicious soup and warm cookies in the evening. I would definitely stay here again. "
United States
Susan
The price is NT$2,934
NT$3,588 total
includes taxes & fees
Dec 28 - Dec 29
Country inn & Suites by Radisson Bolingbrook, I-55
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 Highland Hills Hotel Reviews

Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

10/10 Excellent
"Clean room and friendly staff"
Aslee 3-night trip
Posted 1 day ago
Holiday Inn & Suites Chicago - Downtown by IHG

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Frequently asked questions

What are some accommodations with pools in Highland Hills?
SureStay Plus Hotel by Best Western Chicago Lombard: Hotel, 13-minute walk from Chicago Riverwalk. Features a sauna, an indoor pool, and a snack bar/deli. Crowne Plaza Chicago West Loop by IHG: Hotel, 4-minute walk from Donald E. Stephens Convention Center. Features 3 restaurants, an indoor pool, and complimentary wireless internet access. Hyatt Regency O'Hare Chicago: Hotel, 12-minute walk from Michigan Avenue. Provides a snack bar/deli, an indoor pool, and complimentary wireless internet access. Voco Chicago Downtown - Riverwalk by IHG: Hotel, 10-minute walk from Willis Tower. Features a snack bar/deli, a seasonal outdoor pool, and complimentary wireless internet access. Hilton Chicago O'Hare Airport: Hotel, 13-minute walk from Chicago Riverwalk. Offers 2 restaurants, an indoor pool, and a sauna.
What is there to see and do in Highland Hills?
Make a point to visit attractions like Morton Arboretum and Edge Ice Arena. During your stay, check out sights such as Yorktown Shopping Center, Oakbrook Center Mall, and Drury Lane Theater. Highland Hills appeals to visitors with its array of dining options and major shopping area.
When is the best time to book a hotel with a pool in Highland Hills?
You may want to consider an accommodation that has an outdoor pool if you plan to visit in the warmest months of July, August, or June when the average temp is 71°F. Lodging with an indoor pool may be what you want if you come to town during the coldest months of January, February, or December when the average temperature is 30°F.