Hotels with Swimming Pools in South Side
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Our top choices for South Side hotels with a pool
8.4 out of 10, Very good, (911)
"The property was excellent the rooms fantastic and the staff were equally wonderful and helpful. "
Leilani
The price is S$201
includes taxes & fees
4 Jan - 5 Jan, 2026
8.6 out of 10, Excellent, (2969)
"Great place to stay"
Elisha
The price is S$130
includes taxes & fees
22 Jan - 23 Jan, 2026
8.4 out of 10, Very good, (1579)
"Rooms were very nice and staff was great"
Nancy
The price is S$233
includes taxes & fees
20 Jan - 21 Jan, 2026
8.8 out of 10, Excellent, (3512)
"Really nice hotel"
Saulius
The price is S$153
includes taxes & fees
28 Dec - 29 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileDowntown Chicago
8.8 out of 10, Excellent, (2203)
"Great location, easy parking. "
Maria
The price is S$129
includes taxes & fees
11 Jan - 12 Jan, 2026
9.0 out of 10, Wonderful, (1052)
"Clean room, clean hotel, wonderful restaurant/bar.
AMAZING location! "
Rebecca
The price is S$185
includes taxes & fees
11 Jan - 12 Jan, 2026
8.4 out of 10, Very good, (2180)
"Beautiful hotel! Perfect for a holiday staycation! "
Melissa
The price is S$230
includes taxes & fees
3 Jan - 4 Jan, 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
Hyatt Place Chicago-South/University Medical Center
10/10 Excellent
Chicago Marriott Midway
10/10 Excellent
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