Hotels with Pool & Resorts in South Side from NZ$242

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Check availability on South Side Hotels with Pool

Tonight
29 Jul - 30 Jul
Tomorrow
30 Jul - 31 Jul
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Best South Side Hotels with Pool

The Hoxton Chicago
Relax by the rooftop pool with a stunning city view, surrounded by comfortable lounge chairs and a small table.

The Hoxton Chicago

4.0 star property
9.0 out of 10, Wonderful, (1012)
"Awesome staff. The
pool
was great. Loved The Lazy Bird."
Jennifer
The price is NZ$402
includes taxes & fees
17 Aug - 18 Aug
The Hoxton Chicago
The Wade
Enjoy a sea view from the large window, with a comfortable seating area and unique artwork on display.

The Wade

4.5 star property
8.2 out of 10, Very good, (1133)
"My room had tile damage in the bathroom. Also it was a bit dusty. The overall area was clean around the property. The
pool
is amazing and the area was clean. The room service was great. I’ll definitely come back again. "
Kristina
The price is NZ$263
includes taxes & fees
17 Aug - 18 Aug
The Wade
Best Western River North Hotel
Relax by the rectangular pool surrounded by lounge chairs and umbrellas.

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1020)
"Overall a great stay. Beds were very comfortable and enjoyable. The
pool
was large and led right out to the rooftop terrace. "
Armando
The price is NZ$242
includes taxes & fees
24 Aug - 25 Aug
Best Western River North Hotel
Chicago Marriott Midway
Relax by the serene pool surrounded by lush gardens and a natural ambiance.

Chicago Marriott Midway

3.5 star property
8.4 out of 10, Very good, (862)
"We stayed here overnight before our a.m. flight the next day. Beautiful rooms, nice restaurant, & starbucks. We will definitely stay next time we fly."
Christina
The price is NZ$253
includes taxes & fees
24 Aug - 25 Aug
Chicago Marriott Midway
DoubleTree by Hilton Chicago - Magnificent Mile
Relax by the pool surrounded by lounge chairs and umbrellas, taking in the city skyline views.

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1936)
"Great location. Liked the property and had a great
pool
area"
Leanna
The price is NZ$316
includes taxes & fees
21 Aug - 22 Aug
DoubleTree by Hilton Chicago - Magnificent Mile
Palmer House a Hilton Hotel
Relax by the pool surrounded by comfortable lounge chairs and framed artwork.

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very good, (1819)
"Socializing with a glass of wine in the bar areas was a high priced luxury!
Pool
was wonderful, room was comfortable and staff were outstanding. "
Clarke
The price is NZ$383
includes taxes & fees
21 Aug - 22 Aug
Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown South Loop
Relax by the pool with expansive city views.

Hilton Garden Inn Chicago Downtown South Loop

3.0 star property
8.8 out of 10, Excellent, (1619)
"Perfect location for a parents and kids"
Krystal
The price is NZ$287
includes taxes & fees
24 Aug - 25 Aug
Hilton Garden Inn Chicago Downtown South Loop
Hyatt House Chicago West Loop
Relax by the pool surrounded by a spacious deck and city views.

Hyatt House Chicago West Loop

3.5 star property
8.8 out of 10, Excellent, (1017)
"Wonderful place for a family in the West Loop! The rooms are very large (especially for Chicago). Easy walk to the trains and lots of restaurants nearby. Bonus? The
pool
was great for the kiddos to get a little swimming in. The breakfast in the morning was perfect - enough yummy options for everyone. We will definitely stay again! "
Shannon
The price is NZ$370
includes taxes & fees
24 Aug - 25 Aug
Hyatt House Chicago West Loop
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Relax by the pool surrounded by comfortable seating and city views.

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very good, (3625)
"Such a nice room with a city view."
Kerry
The price is NZ$307
includes taxes & fees
24 Aug - 25 Aug
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Sentral Michigan Avenue
Relax by the pool surrounded by lush greenery and comfortable lounge seating.

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (845)
"Great location across the street from Grant Park. The view was pretty! The kids loved the
pool
and the extra space with two bedrooms. "
Krista
The price is NZ$398
includes taxes & fees
25 Aug - 26 Aug
Sentral Michigan Avenue
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

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent
"Great."
Arjun 4-night trip
Posted 4 days ago
Hyatt Place Chicago-South/University Medical Center
Chinatown Hotel Chicago

Chinatown Hotel Chicago

8/10 Good
"It’s OK "
Pius 2-night trip
Posted 5 days ago
Chinatown Hotel Chicago