Title: Book the Best Hotels with POOL in South Side in 2026 | Expedia.ca

[South Side Travel Guide](https://expedia.ca/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.ca/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)[South Side Vacation Packages](https://expedia.ca/South-Side.d553248635074842823.Destination-Travel-Guides)

![Chicago South Side](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on South Side Hotels with a Pool

Tonight

[Jan 24 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-24&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 25 - Jan 26](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-25&endDate=2026-01-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-30&endDate=2026-02-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-02-06&endDate=2026-02-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for South Side hotels with a pool

![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/74dfee01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Serves lunch, dinner, and happy hour](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/573f8c28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/2fd33e8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Serves lunch, dinner, and happy hour](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/7cf4bf83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago Marriott Midway

[](https://www.expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information)

Bedford Park

8.4/10

Very good

(917 reviews)

"Great service, friendly staff. Great stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Adrian

CA $166

CA $196 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information)

![Indoor pool, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/352e3b39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/693d9c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Banquet hall](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/2ad62276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aloft Chicago Mag Mile

[](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information)

Downtown Chicago

8.6/10

Excellent

(3,057 reviews)

"All around a nice stay for the holiday "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alec

CA $110

CA $129 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information)

![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![42-inch flat-screen TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/58afb443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a419e8db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a0ababda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Chicago/Magnificent Mile Suites

[](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(3,757 reviews)

"Great stay!!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lorenzo Martrel

CA $110

CA $129 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![Indoor pool, open 5:00 AM to 11:00 PM, sun loungers](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/a8da386d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, laptop workspace, free cribs/infant beds](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/085d232b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Food and drink](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/e9e7f382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/c35b1006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### voco Chicago Downtown - Riverwalk by IHG

[](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information)

Downtown Chicago

8.8/10

Excellent

(3,637 reviews)

"Great place to stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

suleman

CA $171

CA $201 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information)

![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/a08c52fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/8e39b688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/d7ae47e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DoubleTree by Hilton Chicago - Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information)

Downtown Chicago

8.8/10

Excellent

(2,259 reviews)

"Great staff, easy check in."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Zachary

CA $117

CA $137 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/da99f4b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/6ec865cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Wade

[](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information)

Downtown Chicago

8.4/10

Very good

(1,631 reviews)

"Easy check in and out, excellent room service and dining menu."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kevin Bradford

CA $149

CA $175 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/b76bffdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/3a5d3e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/b90174ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/6234383e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Centric Chicago Magnificent Mile

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(1,067 reviews)

"Amazing location, excellent service and great pool and hot tub. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tim

CA $151

CA $217 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/66b60053.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Room, 2 Queen Beds, Accessible, City View (Mobility, Accessible Tub)](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/8acc816e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/12cef3af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/c6f61b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Chicago Dwtn - The Mart by IHG

[](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.Hotel-Information)

Downtown Chicago

8.8/10

Excellent

(2,144 reviews)

"Everything about my stay was great!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amelia

CA $159

CA $187 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.Hotel-Information)

![Indoor pool, seasonal outdoor pool, free cabanas, sun loungers](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/fd4d7555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lunch and dinner served](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/d70c748e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/w2880h1919x0y0-235561ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/44865590.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Radisson Blu Aqua Hotel Chicago

[](https://www.expedia.ca/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.Hotel-Information)

Downtown Chicago

8.6/10

Excellent

(1,842 reviews)

"Excellent front desk, rooms, pool/whirlpool and especially gym. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Victoria Lynn Davis

CA $216

CA $289 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/fa7d1870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/20c3f16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/a7afe57a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/f57ccf79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Royal Sonesta Chicago River North

[](https://www.expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(2,419 reviews)

"Lovely staff, very clean hotel, convenient location."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tierra

CA $137

CA $205 total

includes taxes & fees

Feb 5 - Feb 6

[](https://www.expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-08&endDate=2026-02-09&regionId=553248635074842823&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true)

## Top South Side Hotel Reviews

![Hyatt Place Chicago-South/University Medical Center](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg)

### Hyatt Place Chicago-South/University Medical Center

10/10 Excellent

"All great!"

[](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information)

![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/w3836h2161x5y0-7f85e9e1_y.jpg)

### Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent

"I was greeted with a smile we checking our room and we were late. They were very accommodating. They have a bar which we went over to eat from. I don’t know the bartender’s real name we were cold to call her TT. She was the very best ever very kind very sociable and friendly. I will be returning to this property the next time I’m in Chicago. I really had a great experience at this hotel with the staff is also includes the manager the hotel clerk, as well as the security guard. I will give my experience at this hotel five stars."

[](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information)

![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg)

### Chinatown Hotel Chicago

10/10 Excellent

"Get what you pay for! "

[](https://expedia.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information)

![Chicago Marriott Midway](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7_y.jpg)

### Chicago Marriott Midway

10/10 Excellent

"Spent a night! Wish I could have stayed longer. The space was clean and beautifully designed, and the hotel staff were extremely accommodating to my needs. Wish I had gotten to enjoy the menu items, but I had to get back to the airport. The shuttle was also great; it came every 20 minutes, and I loved saving money on ride-sharing back to the airport in the morning. Overall great! "

[](https://expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information)

![Best Western Inn & Suites - Midway Airport](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/92ee0c20_y.jpg)

### Best Western Inn & Suites - Midway Airport

10/10 Excellent

"Courteous staff. Clean rooms."

[](https://expedia.ca/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information)

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- [Flights to Chicago ](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)
- [Flights from Toronto (YYZ) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago)

- [Visit Fuller Park ](https://www.expedia.ca/Chicago-Fuller-Park.dx6132374)
- [Visit Indian Village ](https://www.expedia.ca/Chicago-Indian-Village.dx553248635976382922)
- [Chicago Museum of Science and Industry ](https://www.expedia.ca/Chicago-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction)
- [Obama's House ](https://www.expedia.ca/Obamas-House-Kenwood.d553248621533116333.Vacation-Attraction)
- [Robie House ](https://www.expedia.ca/Robie-House-Hyde-Park.d6064059.Vacation-Attraction)

- [Car rentals near Hyde Park ](https://www.expedia.ca/Car-Rentals-In-Hyde-Park.d117842.Car-Rental-Guide)
- [Hertz Rental Cars in Hyde Park ](https://www.expedia.ca/Hertz-Car-Rentals-In-Hyde-Park.d117842-c40.Car-Rental-Guide-Suppliers)

- [Book Hotels with a Pool in South Side on Expedia.com ](https://www.expedia.com/South-Side-Hotels-Hotel-With-Pool.0-0-d553248635074842823-tHotelwithPool.Travel-Guide-Filter-Hotels)