Title: Adventure Vacations in South Side 2026 | Expedia.ca ![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Adventure Vacations ## Book a Hotel + Flight or Car together to unlock savings - ## 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 Adventure hotel deals in South Side Price found within the past 48 hours. Click for updated prices. ![Marriott Marquis Chicago](https://images.trvl-media.com/lodging/19000000/18180000/18179000/18178914/92b66897_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott Marquis Chicago Near South Side CA $1,628 per person May 15 - May 17 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.2/10 Wonderful! (1,000 reviews) Shower drain was clogged. Discovered this 2 min in with shampoo in hair. Linens did not seem crisp/fresh, hand towel was missing, glass was missing. But good view Reviewed on Mar 23, 2026 ![The Wheeler Mansion](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/18dd5e87_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wheeler Mansion Near South Side CA $1,935 per person May 22 - May 25 found 4 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Chicago (ORD) 9/10 Wonderful! (4 reviews) A unique place to stay near the convention centre. Reviewed on Jun 23, 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/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Adventure holidays in South Side Price found within the past 48 hours. Click for updated prices. ![Marriott Marquis Chicago](https://images.trvl-media.com/lodging/19000000/18180000/18179000/18178914/92b66897_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott Marquis Chicago Near South Side CA $977 per person May 22 - May 25 found 23 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.2/10 Wonderful! (1,000 reviews) Shower drain was clogged. Discovered this 2 min in with shampoo in hair. Linens did not seem crisp/fresh, hand towel was missing, glass was missing. But good view Reviewed on Mar 23, 2026 ![The Wheeler Mansion](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/18dd5e87_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wheeler Mansion Near South Side CA $1,935 per person May 22 - May 25 found 4 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Chicago (ORD) 9/10 Wonderful! (4 reviews) A unique place to stay near the convention centre. Reviewed on Jun 23, 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/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Adventure Hotels in South Side ![Best Western Grant Park Hotel](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/a243f0c9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Grant Park Hotel 1100 S Michigan Ave Chicago IL - 14 min drive from University of Chicago Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ... 8.2/10 Very Good! (2,681 reviews) Free breakfast would be great, rooms primarily bathroom need ventilation fans....also have tvs that allow app download so members can log into their netflix and or hulu Reviewed on Mar 29, 2026 [](https://expedia.ca/Chicago-Hotels-Best-Western-Grant-Park-Hotel.h23023.Hotel-Information) ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Jaslin Hotel 261 West Cermak Rd Chicago IL - 11 min drive from University of Chicago Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ... 8.8/10 Excellent! (1,190 reviews) The entire property is very clean and comfortable! My double room was fine for me, but would have been a little tight with 2 people. The staff is friendly and helpful. Fantastic dining in the area and walkable to convention center and CTA station. Reviewed on Mar 26, 2026 [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![Marriott Marquis Chicago](https://images.trvl-media.com/lodging/19000000/18180000/18179000/18178914/92b66897_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Marriott Marquis Chicago 2121 South Prairie Avenue Chicago IL - 11 min drive from University of Chicago Book a stay at this business-friendly hotel in Chicago. Enjoy 9 restaurants, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ... 9.2/10 Wonderful! (1,000 reviews) Shower drain was clogged. Discovered this 2 min in with shampoo in hair. Linens did not seem crisp/fresh, hand towel was missing, glass was missing. But good view Reviewed on Mar 23, 2026 [](https://expedia.ca/Chicago-Hotels-Marriott-Marquis-Chicago.h18178914.Hotel-Information) [See all 461 properties in South Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248635074842823) 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. ## 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.