Title: Mountain Vacations in South Side 2026 | Expedia.ca ![](https://images.trvl-media.com/place/829/3b8962fc-94e7-486b-84ab-96e09a77459b.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Mountain Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Richard Remington - ## 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 Mountain hotel deals in South Side Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $618 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Все було чудово. Чистий номер з неймовірним виглядом із вікна, смачні сніданки. Засмутило лише одне: руфтоп був закритий у цей період, а він був однією з важливих цікавинок, яка вплинула на вибір саме цього готелю. Reviewed on Jan 3, 2026 ![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 $1,448 per person Mar 24 - Mar 29 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again! Reviewed on Jan 3, 2026 ![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 $850 per person Mar 24 - Mar 29 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) Excellent service from staff. Clean rooms and great location Reviewed on Jan 2, 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $973 per person Mar 24 - Mar 29 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Staff was friendly did amazing job with checking us in Reviewed on Dec 25, 2025 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $898 per person Mar 24 - Mar 29 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Everything was great! Reviewed on Dec 29, 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/2026-02-03/2026-02-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Mountain holidays in South Side Price found within the past 48 hours. Click for updated prices. ![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 $1,163 per person Feb 13 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.6/10 Exceptional! (1,000 reviews) Room was excellent. Everything was clean and the amenities were fantastic. Staff was very warm and helpful. Will go back Reviewed on Jan 2, 2026 ![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 $1,448 per person Mar 24 - Mar 29 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again! Reviewed on Jan 3, 2026 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $1,770 per person Mar 24 - Mar 29 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Emil was a fabulous server at the Lobby Restaurant. I think that’s his name. Tall guy. Becca at front desk also fantastic. The lady who checked us in not so good. Reviewed on Dec 29, 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/2026-02-03/2026-02-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Mountain holidays in South Side Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $543 per person Feb 13 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Все було чудово. Чистий номер з неймовірним виглядом із вікна, смачні сніданки. Засмутило лише одне: руфтоп був закритий у цей період, а він був однією з важливих цікавинок, яка вплинула на вибір саме цього готелю. Reviewed on Jan 3, 2026 ![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 $989 per person Feb 13 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again! Reviewed on Jan 3, 2026 ![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 $636 per person Feb 13 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) Excellent service from staff. Clean rooms and great location Reviewed on Jan 2, 2026 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/2026-02-03/2026-02-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Mountain holidays in South Side Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $618 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Все було чудово. Чистий номер з неймовірним виглядом із вікна, смачні сніданки. Засмутило лише одне: руфтоп був закритий у цей період, а він був однією з важливих цікавинок, яка вплинула на вибір саме цього готелю. Reviewed on Jan 3, 2026 ![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 $726 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) Excellent service from staff. Clean rooms and great location Reviewed on Jan 2, 2026 ![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 $991 per person Mar 14 - Mar 18 just found Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Had a great dinner at Fora before a very short walk to the new years eve event we were headed to and then came back for a great night's sleep in a very comfortable room! All the staff we interacted with were great! Reviewed on Jan 1, 2026 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/2026-02-03/2026-02-10/?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