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

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on South Side Hotels with Pool

This weekend
Next weekend

Best South Side Hotels with Pool

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

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

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

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

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

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

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

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

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

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