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Hillside Hotel with Pool

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Our top choices for Hillside hotels with a 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, (1004)
"Room was very clean, staff was courteous and helpful. Would stay there again"
United States
Amanda
The price is HK$754
HK$844 total
includes taxes & fees
24 Jan - 25 Jan 2026
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1551)
"All was great room view and staff "
United States
STANLEY
The price is HK$723
HK$848 total
includes taxes & fees
19 Jan - 20 Jan 2026
The Wade

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1063)
"Clean room, clean hotel, wonderful restaurant/bar. AMAZING location! "
United States
Rebecca
The price is HK$762
HK$1,122 total
includes taxes & fees
25 Jan - 26 Jan 2026
Hyatt Centric Chicago Magnificent Mile

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3539)
"Great location and breakfast.. can be a bit pricey but worth it. "
Canada
Shaurya
The price is HK$901
HK$1,058 total
includes taxes & fees
28 Jan - 29 Jan 2026
voco Chicago Downtown - Riverwalk by IHG

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2213)
"It was a beautiful stay "
United States
Donald
The price is HK$663
HK$778 total
includes taxes & fees
6 Jan - 7 Jan 2026
DoubleTree by Hilton Chicago - Magnificent Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3000)
"Great place to stay"
United States
Elisha
The price is HK$668
HK$785 total
includes taxes & fees
22 Jan - 23 Jan 2026
Aloft Chicago Mag Mile

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, (1793)
"Great place to stay! Near all the sites to see!"
United States
Rafael
The price is HK$586
HK$688 total
includes taxes & fees
7 Jan - 8 Jan 2026
Hilton Garden Inn Chicago Downtown South Loop

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, (2778)
"Excellent place to stay "
United States
Teniesha
The price is HK$643
HK$983 total
includes taxes & fees
11 Jan - 12 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2349)
"We had a great stay! The experience was great from beginning to end. "
United States
Melanie
The price is HK$863
HK$1,261 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Royal Sonesta Chicago River North

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (4295)
"Amazing staff and perfect location "
United States
Brandi
The price is HK$586
HK$688 total
includes taxes & fees
26 Jan - 27 Jan 2026
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.

Top Hillside Hotel Reviews

Frequently asked questions

What are some accommodation options with pools in Hillside?
Hilton Chicago/Magnificent Mile Suites: Hotel steps from State Street. Offers a full-service spa, an indoor pool and a 24-hour fitness centre. Palmer House a Hilton Hotel: Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool and a health club. Silversmith Hotel Chicago Downtown: Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool and flat-screen televisions. Club Quarters Hotel Wacker at Michigan, Chicago: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool and a sauna. Hilton Chicago: Hotel, 13-minute walk from Chicago Riverwalk. Offers 2 restaurants, an indoor pool and a sauna.
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.

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