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 $1,250 per person Dec 23 - Dec 26 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9/10 Wonderful! (1,011 reviews) great staff and location Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-26/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=18178914&paandie=true&HotelClass=40&dealMarker=hEcxEAl0cQr8TKY7Kq7rzltpVOXFENsUA29O4raUj0ZqK3KNzk-mlUit8TT4cLzK) ![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 $2,145 per person Dec 1 - Dec 8 just found Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9/10 Wonderful! (1,012 reviews) Huge convention center associated hotel. Very nice clean and modern rooms. Lakeside views from the convention are amazing (watch it at Sunrise). Only con is that it's kind of isolated dining wise and from more hip or active parts of the city. taxis/rideshares making a killing over here. Reviewed on Oct 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-01/2025-12-08/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=84736&paandie=true&HotelClass=40&dealMarker=8hXe3TWR6KnKbyZw6VvS4Q9_DPFHRGjdwtMHDWmrdHPAF9TKbraq8lFrKKZqKFxr) 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/2025-11-23/2025-11-30/?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/19000000/18180000/18179000/18178914/6d23e5ad_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott Marquis Chicago Near South Side CA $1,250 per person Dec 23 - Dec 26 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9/10 Wonderful! (1,011 reviews) great staff and location Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-26/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=18178914&paandie=true&HotelClass=40&dealMarker=hEcxEAl0cQr8TKY7Kq7rzltpVOXFENsUA29O4raUj0ZqK3KNzk-mlUit8TT4cLzK) 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/2025-11-23/2025-11-30/?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 $714 per person Dec 30 - Jan 3 found 11 hours ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 8.2/10 Very Good! (2,628 reviews) For the price NO. The best option if it is available is to stay somewhere near the end of one of the L-trains with a day pass and make your way in and around town. Everyone I ask sad the noise from the mechanical things on the roof (9th) floor rooms was horrible. On my floor the road noise and the L-train was almost load. Sub $250 it’s OK, anything higher it’s a VERY maybe stay for me. Dinning options around the area a very good. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-30/2026-01-03/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=23023&paandie=true&dealMarker=hEcxEAl0cQr8TKY7Kq7rzkU80-2X_Uq982axrfZmM_5sxpjA6G31DI9syNimBx90) 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/2025-11-23/2025-11-30/?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! (1,019 reviews) Nice room Reviewed on Oct 21, 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! (2,636 reviews) Very nice place Reviewed on Oct 17, 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! (1,162 reviews) Great hotel Reviewed on Oct 21, 2025 [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) [See all 450 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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)