Find hotels with pools in Highland Hills, Chicago from $102

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Check availability on Highland Hills Hotels with a Pool

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Top 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

3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3413)
"Great hotel!!"
United States
Deja
$99 nightly
The price is $116
Dec 29 - Dec 30
Total with taxes and fees
voco Chicago Downtown - Riverwalk by IHG
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, (2025)
"Great hotel."
United States
Mario
$95 nightly
The price is $112
Dec 22 - Dec 23
Total with taxes and fees
Holiday Inn Chicago Dwtn - The Mart by IHG
Indoor pool, sun loungers
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, (1006)
"Nice hotel in the heart of West Loop. Conveniently close to OTC train station. Enjoyed our stay. "
United States
Paul Okello
$119 nightly
The price is $140
Dec 12 - Dec 13
Total with taxes and fees
Hampton Inn Chicago West Loop Fulton Market Area
Indoor pool
Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop

3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1113)
"great stay, check in was easy"
United States
Bri
$110 nightly
The price is $129
Dec 22 - Dec 23
Total with taxes and fees
Hyatt Place Chicago/Downtown - The Loop
Indoor pool, sun loungers
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, (999)
"amazing stay! "
United States
Sonny
$127 nightly
The price is $149
Dec 12 - Dec 13
Total with taxes and fees
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
Seasonal outdoor pool
The Hoxton Chicago

The Hoxton Chicago

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1008)
"Love the Hoxton, it’s a beautiful hotel and the staff is amazing. "
United States
Sam
$168 nightly
The price is $197
Dec 28 - Dec 29
Total with taxes and fees
The Hoxton Chicago
Indoor pool
Hyatt House Chicago West Loop

Hyatt House Chicago West Loop

3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1110)
"Overall good stay with staff with amazing hospitality "
United States
Emily
$152 nightly
The price is $179
Dec 21 - Dec 22
Total with taxes and fees
Hyatt House Chicago West Loop
Indoor pool, open 6:00 AM to 9:00 PM, sun loungers
Nobu Hotel Chicago

Nobu Hotel Chicago

5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (752)
"Great location, amenities and staff. "
United States
Nicholas
$250 nightly
The price is $294
Dec 21 - Dec 22
Total with taxes and fees
Nobu Hotel Chicago
Indoor pool
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, (352)
"Clean nice place to stay "
United States
Daryl
$87 nightly
The price is $102
Dec 7 - Dec 8
Total with taxes and fees
Hampton Inn & Suites Chicago Medical District UIC
Outdoor spa tub
Level Chicago - River North

Level Chicago - River North

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (779)
"Good location to visit the riverfront...walkable"
United States
Patricia
$177 nightly
The price is $208
Dec 14 - Dec 15
Total with taxes and fees
Level 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 Highland Hills Hotel Reviews

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"The staff was so nice !"
Yan 1-night trip
Posted 11 hours ago
Hyatt Regency O'Hare Chicago

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: Offers a snack bar/deli, an indoor pool, and free self parking. Hilton Chicago O'Hare Airport: Hotel, 13-minute walk from Chicago Riverwalk. Provides 2 restaurants, an indoor pool, and a sauna. Voco Chicago Downtown - Riverwalk by IHG: Hotel located near Donald E. Stephens Convention Center. Features complimentary wireless internet access, an indoor pool, and Smart TVs. Canopy by Hilton Chicago Central Loop: Hotel, 12-minute walk from Michigan Avenue. Offers a snack bar/deli, an indoor pool, and complimentary wireless internet access.
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.

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