Title: Adventure 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 Adventure 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 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/19000000/18180000/18179000/18178914/6d23e5ad_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott Marquis Chicago Near South Side CA $547 per person Dec 12 - Dec 14 just found Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,007 reviews) Solo female traveler. Came to town for a metal show. Hotel was four blocks from the venue. Area felt safe and friendly enough to walk back to the hotel by myself after midnight. The room had a lovely view, also very quiet and well maintained. 10/10 would stay again Reviewed on Oct 5, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-14/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=18178914&paandie=true&HotelClass=40&dealMarker=M6lYpVyqY-8qIQUEWY_Su1wLcjYjPD3gE0Qq-5cSXtP3pCxpmWnBXc7ovPg7G2fb) ![The Wheeler Mansion](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/896f58e6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wheeler Mansion Near South Side CA $1,090 per person Dec 12 - Dec 14 just found Roundtrip flight included Toronto (YTO) to Chicago (ORD) 10/10 Exceptional! (2 reviews) A unique place to stay near the convention centre. Reviewed on Jun 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-14/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=7818107&paandie=true&HotelClass=40&dealMarker=M6lYpVyqY-8qIQUEWY_Su1wLcjYjPD3gE0Qq-5cSXtNz28-_N1L0wQUECUli52KO) ![Hyatt Regency McCormick Place Chicago ](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/64dd2430_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency McCormick Place Chicago Near South Side CA $1,049 per person Dec 12 - Dec 14 found 3 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Chicago (ORD) 9.2/10 Wonderful! (1,019 reviews) Nice. Not good food options. Reviewed on Oct 9, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-14/?FromAirport=YOW&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=84736&paandie=true&HotelClass=40&dealMarker=M6lYpVyqY-8qIQUEWY_Su6c1lJnDCIM-nFgv2MHLb06WvHgu_BTje3kK5ma5qM48) 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/2025-11-11/2025-11-18/?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. ![Hyatt Regency McCormick Place Chicago ](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/64dd2430_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency McCormick Place Chicago Near South Side CA $1,046 per person Nov 14 - Nov 17 found 24 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.2/10 Wonderful! (1,019 reviews) Nice. Not good food options. Reviewed on Oct 9, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-17/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=84736&paandie=true&HotelClass=40&dealMarker=6CuNs0vxu2uILjtBFDt_O2nyEXF7BkY-xXTEJ9IewBM2cF-KDwLkzpojBTJZf6LD) 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/2025-11-11/2025-11-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Adventure holidays in South Side Price found within the past 48 hours. Click for updated prices. ![Best Western Grant Park Hotel](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/a243f0c9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Best Western Grant Park Hotel Downtown Chicago CA $606 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 8.2/10 Very Good! (2,624 reviews) It’s the most beautiful place that I have ever been, fabulous interior design and so comfortable, so on Reviewed on Oct 11, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23023&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_O6_kl7Wu-FgtVoecd161uTmQiwIR0KvZWTVi5BnFkx3U) ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Jaslin Hotel Chinatown CA $825 per person Dec 15 - Dec 19 found 2 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 8.8/10 Excellent! (1,148 reviews) Small rooms, no where to put clothes (no dresser). Ironing board broken and stains on iron damaged my wifes dress. No parking or even comp parking. There are better options. Reviewed on Oct 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=13320264&paandie=true&dealMarker=M6lYpVyqY-8qIQUEWY_Su6BlFzsO_yQ8el-x0H4cJnhNFf9C7CLbeCCEvT0ovYfM) ![Marriott Marquis Chicago](https://images.trvl-media.com/lodging/19000000/18180000/18179000/18178914/6d23e5ad_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott Marquis Chicago Near South Side CA $1,445 per person Dec 15 - Dec 19 found 2 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.2/10 Wonderful! (1,007 reviews) Solo female traveler. Came to town for a metal show. Hotel was four blocks from the venue. Area felt safe and friendly enough to walk back to the hotel by myself after midnight. The room had a lovely view, also very quiet and well maintained. 10/10 would stay again Reviewed on Oct 5, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=18178914&paandie=true&dealMarker=M6lYpVyqY-8qIQUEWY_Su6BlFzsO_yQ8el-x0H4cJnjuTyHFhguYiUqxWfBlyRgi) 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/2025-11-11/2025-11-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Adventure Hotels in South Side ![Hyatt Regency McCormick Place Chicago ](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/64dd2430_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency McCormick Place Chicago 2233 S Martin Luther King Dr, Chicago, IL - 11 min drive from University of Chicago Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ... 9/10 Wonderful! (1,004 reviews) "Nice. Not good food options." Reviewed on Oct 9, 2025 [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-McCormick-Place.h84736.Hotel-Information) ![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 ... 8/10 Very Good! (2,622 reviews) "Clean room, positioned in downtown close to Millennial Park and shopping areas. Valet parking only for $58/ night" Reviewed on Oct 3, 2025 [](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 3-star 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 ... 8.8/10 Excellent! (1,171 reviews) "5 minute drive from Soldier Field. Parking was inconvenient and we had to park 2 blocks away. But nice and quiet hotel." Reviewed on Oct 10, 2025 [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) [See all 452 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. ![](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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)