Title: Scuba Diving Vacations in South Side 2025/2026 | Expedia.ca ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Scuba Diving Vacations ## Book a Hotel + Flight or Car together to unlock savings Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ### Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## 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 $722 per person Nov 27 - Nov 30 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9/10 Wonderful! (1,004 reviews) The room was perfect and the front staff were exceptional. Our stay was amazing! Reviewed on Sep 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-27/2025-11-30/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&HotelClass=40&dealMarker=VU-ipLZoVS5VE3pWZZ03yWYmHxPfj1HbhggpGQEXo0v6LD1EhKr_yzY8Ol4LfLZi) ![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 $1,404 per person Oct 23 - Oct 26 found 24 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Got pick pocketed in the elevator. I really like this hotel. Plan to return. Reviewed on Sep 8, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-10-23/2025-10-26/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=1x9-ayHdIFt-ajkLsImd9mbiEIU5HL0ODFgR0q9ZRbs6pvKdv1MqtsuLBttZJyaF) ![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 $1,248 per person Nov 27 - Nov 30 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Worth every penny! Not much more than the "average" hotel when comparing all of the amenities. Will definitely stay here again! Reviewed on Sep 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-27/2025-11-30/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=VU-ipLZoVS5VE3pWZZ03yfmjBiRh7P2FdkYuT7eG5ZAkPRfgxy6HnQt87cLXvuFw) ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago CA $1,748 per person Nov 14 - Nov 17 found 5 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,005 reviews) Great place to stay. Reviewed on Sep 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-17/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6309326&paandie=true&HotelClass=40&dealMarker=vSNH3z35aNCrcxkw8Nq-8mY2nXElcb6OTT46BxlKlhRoZHo9oWDuRDXJXsQFK4SR) ![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 $742 per person Dec 12 - Dec 15 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,222 reviews) I was so disappointed in my stay at the Emily. For almost $500/night I was expecting nice, spacious rooms. The room was so small, the sink was in the hallway, the bed was so uncomfortable, dingy design. I’ve stayed at better Aloft or Moxy rooms. The food at Fora, the hotel restaurant, is uninspired and unseasoned. The brunch chiliques were bland. Skip this hotel in west loop and stay at the hoxton instead Reviewed on Sep 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-15/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=8JE9ilh0U4aPFCZmBiTzrgLoLESjJ8FwA9cE4vrRGRM9MqN4DUnFyqgRENZLcjOU) 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/2025-10-23/2025-10-30/?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 $1,248 per person Nov 27 - Nov 30 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Worth every penny! Not much more than the "average" hotel when comparing all of the amenities. Will definitely stay here again! Reviewed on Sep 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-27/2025-11-30/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=VU-ipLZoVS5VE3pWZZ03yfmjBiRh7P2FdkYuT7eG5ZAkPRfgxy6HnQt87cLXvuFw) ![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 $1,404 per person Oct 23 - Oct 26 found 24 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Got pick pocketed in the elevator. I really like this hotel. Plan to return. Reviewed on Sep 8, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-10-23/2025-10-26/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=1x9-ayHdIFt-ajkLsImd9mbiEIU5HL0ODFgR0q9ZRbs6pvKdv1MqtsuLBttZJyaF) ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago CA $1,748 per person Nov 14 - Nov 17 found 5 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,005 reviews) Great place to stay. Reviewed on Sep 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-17/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6309326&paandie=true&HotelClass=50&dealMarker=vSNH3z35aNCrcxkw8Nq-8mY2nXElcb6OTT46BxlKlhRoZHo9oWDuRDXJXsQFK4SR) 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/2025-10-23/2025-10-30/?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 $722 per person Nov 27 - Nov 30 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9/10 Wonderful! (1,004 reviews) The room was perfect and the front staff were exceptional. Our stay was amazing! Reviewed on Sep 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-27/2025-11-30/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&HotelClass=40&dealMarker=VU-ipLZoVS5VE3pWZZ03yWYmHxPfj1HbhggpGQEXo0v6LD1EhKr_yzY8Ol4LfLZi) ![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 $1,313 per person Oct 23 - Oct 26 found 24 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Worth every penny! Not much more than the "average" hotel when comparing all of the amenities. Will definitely stay here again! Reviewed on Sep 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-10-23/2025-10-26/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=1x9-ayHdIFt-ajkLsImd9mbiEIU5HL0ODFgR0q9ZRbt0-g2bFeOPSCpTtC1PQ0Oz) ![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 $1,404 per person Oct 23 - Oct 26 found 24 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Got pick pocketed in the elevator. I really like this hotel. Plan to return. Reviewed on Sep 8, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-10-23/2025-10-26/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=1x9-ayHdIFt-ajkLsImd9mbiEIU5HL0ODFgR0q9ZRbs6pvKdv1MqtsuLBttZJyaF) 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/2025-10-23/2025-10-30/?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. ![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 $777 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.2/10 Wonderful! (291 reviews) Had a great uneventful stay Reviewed on Sep 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=ufQn9pnjrb_Hh0g5CYIjH8w5vVQq5cbDw_-cui7BebK7ahhM8ouR9F1RLA2n5bI5) ![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 $1,370 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Worth every penny! Not much more than the "average" hotel when comparing all of the amenities. Will definitely stay here again! Reviewed on Sep 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=nbRYI0MPJ1BfhoTp2t1EsWjN2vRb6YrJBQ6fcEsdSF10vd0FyjNAJRZ4JVq8bC6B) ![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 $1,331 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Got pick pocketed in the elevator. I really like this hotel. Plan to return. Reviewed on Sep 8, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=nbRYI0MPJ1BfhoTp2t1EsWjN2vRb6YrJBQ6fcEsdSF048aE702GvUnS0HO6ltUSO) 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/2025-10-23/2025-10-30/?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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)