Title: Scuba Diving Vacations in South Side 2026/2026 | Expedia.ca ![](https://images.trvl-media.com/place/5719117/eadab43c-a88e-4198-bdcd-703715c2ebbd.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Scuba Diving Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by by Midway Intl Airport - ## 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 Scuba Diving hotel deals in South Side Price found within the past 48 hours. Click for updated prices. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $447 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) great staff...loved our stay. Reviewed on Nov 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&HotelClass=40&dealMarker=a27Pp9qmgRV6eid2GzNeKS4FYIgTN3KE3ibhq5KX0HRyGa6VQ7rJIpJ66UNp40Wv) ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago CA $764 per person Feb 19 - Feb 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay. Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-19/2026-02-22/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=1h-QEUGO7q1FgOFcC__mr6M7VftBGl7DsiPV9SpSLkxGoO4bz-sJNQpXqYNZCgaa) ![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 $676 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Its room was perfect the only bad part was their was a couple stains in the bathroom wall Reviewed on Dec 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&HotelClass=40&dealMarker=msY5_QYRkz8dm0P8LIGNs0c1MaRu8gro00P0Yp43X0pRTGuHds6Dd8ZAMi4svalB) ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $544 per person Feb 12 - Feb 15 found 23 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in. Reviewed on Nov 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=95823687&paandie=true&HotelClass=40&dealMarker=2MaV768TBcz8HM99OhHJ6JflCyBNAqlTw4g-Dr14U8Mr0AOEZK9QuCT_zgzO85iL) ![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 $792 per person Feb 19 - Feb 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful. Reviewed on Dec 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-19/2026-02-22/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=1h-QEUGO7q1FgOFcC__mr6M7VftBGl7DsiPV9SpSLkw9mzrsWE4J5oa1kA7ujn4J) 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/2026-01-02/2026-01-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Scuba Diving 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 $792 per person Feb 19 - Feb 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful. Reviewed on Dec 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-19/2026-02-22/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=1h-QEUGO7q1FgOFcC__mr6M7VftBGl7DsiPV9SpSLkw9mzrsWE4J5oa1kA7ujn4J) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $865 per person Feb 12 - Feb 15 found 23 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.6/10 Exceptional! (1,000 reviews) It is always an amazing place to stay Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=2MaV768TBcz8HM99OhHJ6JflCyBNAqlTw4g-Dr14U8O_hRGYQZv6z6PAO73jtneG) ![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 $1,048 per person Feb 19 - Feb 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) The staff was amazing. Will be making a return stay. Reviewed on Nov 30, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-19/2026-02-22/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&HotelClass=50&dealMarker=1h-QEUGO7q1FgOFcC__mr32SXEKcEG6NZuIqVsi72Vk3se4M0JavPtPzfUYvNgYT) 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/2026-01-02/2026-01-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Scuba Diving holidays in South Side Price found within the past 48 hours. Click for updated prices. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $377 per person Feb 19 - Feb 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) great staff...loved our stay. Reviewed on Nov 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-19/2026-02-22/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&HotelClass=40&dealMarker=1h-QEUGO7q1FgOFcC__mr9CXgpjqGtpZ7NCa5-DjiR6KF_38SnI4en7xP1ddLwAP) ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago CA $764 per person Feb 19 - Feb 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay. Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-19/2026-02-22/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=1h-QEUGO7q1FgOFcC__mr6M7VftBGl7DsiPV9SpSLkxGoO4bz-sJNQpXqYNZCgaa) ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $544 per person Feb 12 - Feb 15 found 23 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in. Reviewed on Nov 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=95823687&paandie=true&HotelClass=40&dealMarker=2MaV768TBcz8HM99OhHJ6JflCyBNAqlTw4g-Dr14U8Mr0AOEZK9QuCT_zgzO85iL) 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/2026-01-02/2026-01-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Scuba Diving holidays in South Side Price found within the past 48 hours. Click for updated prices. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $447 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) great staff...loved our stay. Reviewed on Nov 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=a27Pp9qmgRV6eid2GzNeKS4FYIgTN3KE3ibhq5KX0HRyGa6VQ7rJIpJ66UNp40Wv) ![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 $676 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Its room was perfect the only bad part was their was a couple stains in the bathroom wall Reviewed on Dec 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=msY5_QYRkz8dm0P8LIGNs0c1MaRu8gro00P0Yp43X0pRTGuHds6Dd8ZAMi4svalB) ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago CA $719 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (317 reviews) The room was beautiful and clean and a good city view of the city Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=msY5_QYRkz8dm0P8LIGNs3iGdmA1Y-44jSsUchYkR7aSYEIItIew0mh4TRApOvMC) 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/2026-01-02/2026-01-09/?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 ![QR code to download the app](data:image/png;base64,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)