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. ![Arlo Chicago](https://images.trvl-media.com/lodging/27000000/26920000/26910700/26910691/747fff56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arlo Chicago Downtown Chicago CA $785 per person Dec 3 - Dec 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,826 reviews) The Arlo Hotel treats everyone like they are special and important. It's a must-try for business, personal, or romantic getaways. The city view is amazing. Reviewed on Sep 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-03/2025-12-06/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=26910691&paandie=true&HotelClass=40&dealMarker=1x9-ayHdIFt-ajkLsImd9oQSHhbGqpf4R8SQkxhFumxFT3yBvUGH1BQCMWJK2GK8) ![Art Villa ](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/a9b39b37_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Art Villa West Town CA $1,132 per person Nov 4 - Nov 7 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 10/10 Exceptional! (2 reviews) [](https://expedia.ca/go/package/search/FlightHotel/2025-11-04/2025-11-07/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115163763&paandie=true&HotelClass=40&dealMarker=9MMwMxn2uC3zopT06yPCUwNmBACGTLegHIYEFatTlAughiWIFQvOMaDTw6Jxvnfi) ![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 $1,253 per person Dec 3 - Dec 6 found 1 day 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/2025-12-03/2025-12-06/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=1x9-ayHdIFt-ajkLsImd9k6H1SJpcAAah5H6gpIqhJj4zVvb-5q-HMd-UjUVXFlJ) ![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 $1,569 per person Oct 30 - Nov 2 found 1 day ago Roundtrip flight included Toronto (YTZ) 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/2025-10-30/2025-11-02/?FromAirport=YTZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=7nSRQFwzw97AaCjbY_t4qhNwc-vDvTHtbSXk9fX7qFClVtE-ZBw9l8nu4Q1F-BXE) ![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 1 day 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-8m1VODRRJmHJXArziwu7PvU4_pSsgzbywMwosBeoN5th) 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/2025-10-24/2025-10-31/?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. ![Art Villa ](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/a9b39b37_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Art Villa West Town CA $1,132 per person Nov 4 - Nov 7 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 10/10 Exceptional! (2 reviews) [](https://expedia.ca/go/package/search/FlightHotel/2025-11-04/2025-11-07/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115163763&paandie=true&HotelClass=50&dealMarker=9MMwMxn2uC3zopT06yPCUwNmBACGTLegHIYEFatTlAughiWIFQvOMaDTw6Jxvnfi) ![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 $1,253 per person Dec 3 - Dec 6 found 1 day 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/2025-12-03/2025-12-06/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=1x9-ayHdIFt-ajkLsImd9k6H1SJpcAAah5H6gpIqhJj4zVvb-5q-HMd-UjUVXFlJ) ![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 $1,569 per person Oct 30 - Nov 2 found 1 day ago Roundtrip flight included Toronto (YTZ) 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/2025-10-30/2025-11-02/?FromAirport=YTZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=7nSRQFwzw97AaCjbY_t4qhNwc-vDvTHtbSXk9fX7qFClVtE-ZBw9l8nu4Q1F-BXE) 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/2025-10-24/2025-10-31/?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. ![Art Villa ](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/a9b39b37_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Art Villa West Town CA $1,132 per person Nov 4 - Nov 7 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 10/10 Exceptional! (2 reviews) [](https://expedia.ca/go/package/search/FlightHotel/2025-11-04/2025-11-07/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115163763&paandie=true&HotelClass=40&dealMarker=9MMwMxn2uC3zopT06yPCUwNmBACGTLegHIYEFatTlAughiWIFQvOMaDTw6Jxvnfi) ![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 $1,253 per person Dec 3 - Dec 6 found 1 day 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/2025-12-03/2025-12-06/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=1x9-ayHdIFt-ajkLsImd9k6H1SJpcAAah5H6gpIqhJj4zVvb-5q-HMd-UjUVXFlJ) ![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 $1,569 per person Oct 30 - Nov 2 found 1 day ago Roundtrip flight included Toronto (YTZ) 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/2025-10-30/2025-11-02/?FromAirport=YTZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=7nSRQFwzw97AaCjbY_t4qhNwc-vDvTHtbSXk9fX7qFClVtE-ZBw9l8nu4Q1F-BXE) 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/2025-10-24/2025-10-31/?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 $656 per person Nov 10 - Nov 14 found 16 hours ago Roundtrip non-stop flight included Toronto (YYZ) 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/2025-11-10/2025-11-14/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=MGrEOyH8UEOal4VvLgc6B78nyDu-7D7cGFQGVmrYkVkf_LDwfgPw8amZEimz_BXg) ![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 $1,018 per person Nov 29 - Dec 3 found 16 hours ago Roundtrip non-stop flight included Vancouver (YVR) 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/2025-11-29/2025-12-03/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=MGrEOyH8UEOal4VvLgc6B3ISUJU92dtAitQN5HP2LLRn7Wj8N6JZipFzlejrfqUx) ![The Allegro Royal Sonesta Hotel Chicago Loop](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Allegro Royal Sonesta Hotel Chicago Loop Downtown Chicago CA $712 per person Nov 29 - Dec 3 found 16 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9/10 Wonderful! (2,027 reviews) Good room. Good location to train. Area is a little suspect Reviewed on Sep 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-29/2025-12-03/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=34496&paandie=true&dealMarker=MGrEOyH8UEOal4VvLgc6B60ONQoKiatETjr6LW0Vy0USioaSUh5z0lbbQ22hmmSm) 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/2025-10-24/2025-10-31/?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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)