South Side Hotels with Swimming Pool
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on South Side Hotels with Swimming Pools
Tonight
6 Aug - 7 AugTomorrow
7 Aug - 8 AugThis weekend
7 Aug - 9 AugNext weekend
14 Aug - 16 AugOur top choices for South Side hotels with a pool
1. Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South LoopDowntown Chicago
- Dive into city centre luxury with a rejuvenating pool experience close to Chicago landmarks.
RM658
RM782 total
includes taxes & fees
31 Aug - 1 Sept
2. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
Homewood Suites by Hilton Chicago West Loop Fulton Mkt AreaDowntown Chicago
- Swim year-round at the urban indoor pool oasis with sun loungers and city centre Chicago views.
RM553
RM658 total
includes taxes & fees
23 Aug - 24 Aug
3. Hilton Chicago
Hilton ChicagoDowntown Chicago
- Soak in relaxation at this historic Chicago hotel's indoor pool with spa amenities nearby.
RM797
RM1,068 total
includes taxes & fees
30 Aug - 31 Aug
4. Chicago Marriott Midway
Chicago Marriott MidwayBedford Park
- Splash into luxury at Chicago Marriott Midway's indoor pool, open from 5 AM to 11 PM for all-day aquatic enjoyment.
RM659
RM774 total
includes taxes & fees
16 Aug - 17 Aug
5. Sentral Michigan Avenue
Sentral Michigan AvenueDowntown Chicago
- Indoor pool oasis at upscale Michigan Avenue aparthotel offers year-round swimming enjoyment.
RM619
RM847 total
includes taxes & fees
31 Aug - 1 Sept
6. Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel ChicagoDowntown Chicago
- Luxurious indoor and seasonal outdoor pools form a relaxing oasis near Millennium Park and Michigan Avenue.
RM897
RM1,193 total
includes taxes & fees
2 Sept - 3 Sept
7. DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileDowntown Chicago
- Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
RM658
RM782 total
includes taxes & fees
30 Aug - 31 Aug
8. Palmer House a Hilton Hotel
Palmer House a Hilton HotelDowntown Chicago
- Dive into urban tranquility at the Palmer House pool, where historic charm meets modern luxury.
RM818
RM1,094 total
includes taxes & fees
30 Aug - 31 Aug
View all properties
Top South Side Hotel Reviews
Chinatown Hotel Chicago
10/10 Excellent
"Greta everything. Coming back. Thank you!!"
Chicago Lake Shore Hotel
10/10 Excellent
"The room was clean and well laid-out / comfy bed / very helpful staff / parking was super convenient"
Explore a world of travel with Expedia
- 3 Star Hotels in The Loop
- Gay friendly Hotels in Bedford Park
- Hotels with free parking in Brookfield
- Beach Resorts in Chicago
- Boutique Hotels in Chicago
- Budget Hotels in Chicago
- Family friendly Hotels in Chicago
- Gay friendly Hotels in Chicago
- Hotels with kitchenette in Chicago
- Hotels with Swimming Pools in Chicago
- Luxury Hotels in Chicago
- Nh Hotels in Chicago
- Pet friendly Hotels in Chicago
- Relais & Chateaux Hotels in Chicago
- Romantic Hotels in Chicago
- Hotels with Spa in Chicago
- Starwood Capital Hotels in Chicago
- Chicago Hotels
- Chicago Museum Campus Hotels
- Aparthotels in Chicago
- Chinatown Hotels
- Budget Hotels in Cook County
- Hotels with Bars / Lounges in Downtown Chicago
- Hotels with Gyms in Downtown Chicago
- Hotels with Views in Downtown Chicago
- Luxury Hotels in Downtown Chicago
- Romantic Hotels in Downtown Chicago
- Downtown Chicago Hotels
- Hotels with indoor pool in Hillside
- Pet friendly Hotels in Hillside
- Hotels near House of Blues Chicago
- Gay friendly Hotels in Hyde Park
- Hilton Hotels in Hyde Park
- Hotels with Gyms in Hyde Park
- Aparthotels in Indiana Station
- Kenwood Hotels
- B&B in LaSalle Street Station
- Hotels near Lighthouse ArtSpace Chicago
- Little Italy Hotels
- Hotels near Lollapalooza
- Boutique Hotels in Magnificent Mile
- Hotels with smoking rooms in Magnificent Mile
- Hotels near McCormick Place
- Hotels near Millennium Park
- Near West Side Hotels
- Hotels near Obama's House
- Hostels in Quincy Metro Station
- Gay friendly Hotels in Sleepy Hollow
- Beach Resorts in South Loop
- Boutique Hotels in The Loop
- Gay friendly Hotels in The Loop
- The Loop Hotels
- Hotels near University of Chicago
- Hotels near University of Illinois Chicago
- Hotels with Gyms in West Loop
- Woodlawn Hotels
- Flights to Chicago
- Flights from Anchorage (ANC) to Chicago (MDW)
- Flights from Baton Rouge (BTR) to Chicago (MDW)
- Flights from Horsham (HSM) to Chicago (MDW)
- Flights from Seoul (ICN) to Chicago (MDW)
- Flights from Iowa City (IOW) to Chicago (MDW)
- Flights from Kuala Lumpur (KUL) to Chicago (ORD)
- Flights from Chennai (MAA) to Chicago (MDW)
- Flights from Majuro (MAJ) to Chicago (MDW)
- Flights from Orlando (MCO) to Chicago (MDW)
- Flights from Monterey (MRY) to Chicago (MDW)
- Flights from Portland (PDX) to Chicago (MDW)
- Flights from Pittsburgh (PIT) to Chicago (MDW)
- Flights from South Bend (SBN) to Chicago (MDW)
- Flights from Louisville (SDF) to Chicago (MDW)
- Flights from Yanbo (YNB) to Chicago (MDW)
- Flights from Montreal (YUL) to Chicago (MDW)
- 360 CHICAGO
- Abbott Park
- Bally's Casino Chicago
- Buckingham Fountain
- Burnham Park
- Visit Canaryville
- Visit Downtown Chicago
- Visit Magnificent Mile
- Visit South Loop
- Visit The Loop
- Visit Chicago
- Cloud Gate
- Design Museum of Chicago
- Elijah Muhammad House
- Grace Abbott Homes Holidays
- Holy Name Cathedral
- Beach Holiday Packages Far Southwest Side
- Magnificent Mile Holidays
- Monadnock Building
- Robie House
- Roseland Holidays