Hotels with Swimming Pool in South Side, Chicago
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Check availability on South Side Hotels with Swimming Pool
Our top choices for South Side hotels with a pool
8.4 out of 10, Very Good, (912)
"The property was excellent the rooms fantastic and the staff were equally wonderful and helpful. "
Leilani
The price is P7,836
P9,205 total
includes taxes & fees
Jan 4 - Jan 5, 2026
8.6 out of 10, Excellent, (2971)
"Great place to stay"
Elisha
The price is P5,059
P5,939 total
includes taxes & fees
Jan 22 - Jan 23, 2026
8.4 out of 10, Very Good, (1579)
"Rooms were very nice and staff was great"
Nancy
The price is P7,576
P10,656 total
includes taxes & fees
Jan 20 - Jan 21, 2026
8.8 out of 10, Excellent, (3514)
"Really nice hotel"
Saulius
The price is P5,950
P6,985 total
includes taxes & fees
Dec 28 - Dec 29
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileDowntown Chicago
8.8 out of 10, Excellent, (2206)
"Great location, easy parking. "
Maria
The price is P5,017
P5,889 total
includes taxes & fees
Jan 4 - Jan 5, 2026
9.0 out of 10, Wonderful, (1052)
"Clean room, clean hotel, wonderful restaurant/bar.
AMAZING location! "
Rebecca
The price is P5,765
P8,494 total
includes taxes & fees
Jan 2 - Jan 3, 2026
8.4 out of 10, Very Good, (2175)
"Beautiful hotel! Perfect for a holiday staycation! "
Melissa
The price is P7,718
P10,531 total
includes taxes & fees
Jan 2 - Jan 3, 2026
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 South Side Hotel Reviews
Best Western Inn & Suites - Midway Airport
10/10 Excellent
