Title: Waterpark Vacations in South Side 2026 | Expedia.ca ![](https://images.trvl-media.com/place/829/3b8962fc-94e7-486b-84ab-96e09a77459b.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Waterpark Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Richard Remington - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Flight and Waterpark hotel deals in South Side Price found within the past 48 hours. Click for updated prices. ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $677 per person Jan 31 - Feb 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Staff was friendly did amazing job with checking us in Reviewed on Dec 25, 2025 ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $679 per person Mar 13 - Mar 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) The cleanliness of the rooms was great and the breakfast buffet was second to none! Location, location, location….. was the best! One block away from the Magnificent Mile, restaurants, and can I say Trader Joe’s? We will definitely come back. Reviewed on Dec 25, 2025 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $979 per person Jan 31 - Feb 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Loved it here and would stay again! Everything was perfect! Reviewed on Dec 21, 2025 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,189 per person Jan 31 - Feb 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Absolutely fantastic hotel great service, you couldn’t ask for more. Reviewed on Dec 3, 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $1,276 per person Jan 31 - Feb 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Service and clean room - paying attention to the details Reviewed on Dec 22, 2025 Don't see what you're looking for? See all available trips from Columbus to South Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-26/2026-02-02/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Waterpark holidays in South Side Price found within the past 48 hours. Click for updated prices. ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $979 per person Jan 31 - Feb 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Loved it here and would stay again! Everything was perfect! Reviewed on Dec 21, 2025 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,189 per person Jan 31 - Feb 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Absolutely fantastic hotel great service, you couldn’t ask for more. Reviewed on Dec 3, 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $1,276 per person Jan 31 - Feb 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Service and clean room - paying attention to the details Reviewed on Dec 22, 2025 Don't see what you're looking for? See all available trips from Columbus to South Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-26/2026-02-02/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Waterpark holidays in South Side Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $673 per person Mar 14 - Mar 17 found 3 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) The cleanliness of the rooms was great and the breakfast buffet was second to none! Location, location, location….. was the best! One block away from the Magnificent Mile, restaurants, and can I say Trader Joe’s? We will definitely come back. Reviewed on Dec 25, 2025 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,017 per person Mar 14 - Mar 17 found 3 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Loved it here and would stay again! Everything was perfect! Reviewed on Dec 21, 2025 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $765 per person Mar 14 - Mar 17 found 3 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Staff was friendly did amazing job with checking us in Reviewed on Dec 25, 2025 Don't see what you're looking for? See all available trips from Columbus to South Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-26/2026-02-02/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Waterpark holidays in South Side Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $538 per person Feb 4 - Feb 8 found 14 hours ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) The cleanliness of the rooms was great and the breakfast buffet was second to none! Location, location, location….. was the best! One block away from the Magnificent Mile, restaurants, and can I say Trader Joe’s? We will definitely come back. Reviewed on Dec 25, 2025 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,267 per person Feb 27 - Mar 3 found 7 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Loved it here and would stay again! Everything was perfect! Reviewed on Dec 21, 2025 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $848 per person Feb 27 - Mar 3 found 7 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Staff was friendly did amazing job with checking us in Reviewed on Dec 25, 2025 Don't see what you're looking for? See all available trips from Columbus to South Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-26/2026-02-02/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## More Vacations Ideas [Flights to South Side ](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[ South Side Hotels ](https://expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[ South Side Vacation Rentals ](https://expedia.ca/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[ South Side Car Rentals ](https://expedia.ca/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)[ South Side Vacations ](https://expedia.ca/South-Side.d553248635074842823.Destination-Travel-Guides)[ Things to do in South Side ](https://expedia.ca/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app