Title: Mountain Vacations in West Side 2025/2026 | Expedia.ca ![](https://images.trvl-media.com/place/6350695/b009c703-f7ab-4e4c-95a4-4b883071adef.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # West Side Mountain 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 Mountain hotel deals in West Side Price found within the past 48 hours. Click for updated prices. ![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 $645 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,004 reviews) Clean room, friendly staff, great location and within walking distance from all shops! Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&HotelClass=40&dealMarker=QpLfFRqLVDnisD62S_OWRnt1WJ_djA44RckJHusFK08qYAIeiHhj4yGJtdZGY6f4) ![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 $706 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) The bed was extremly comfortable Staff was very attentive. Highly recommend Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=QpLfFRqLVDnisD62S_OWRhj5KBURJ4dwaYsNvx6HEhQbJpw7mSJFfFv3NEd20zkK) ![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 $1,300 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Awesome room amazing tub even better service Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=QpLfFRqLVDnisD62S_OWRmThmDVbnZKR8JLgsSfFKFav-_ObckwIVhcfCnR_PZLe) ![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 $803 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,222 reviews) I stayed here for one night for business travel. The room was huge. Great mini bar options. I had a nice breakfast at the restaurant. Reviewed on Oct 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=QpLfFRqLVDnisD62S_OWRrNEB3AuMjACE0GXP59C-v5T6HIqgEnDBLTDNq1ez6vH) ![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 $1,066 per person Dec 28 - Dec 31 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 10/10 Exceptional! (2 reviews) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2025-12-31/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115163763&paandie=true&HotelClass=40&dealMarker=QpLfFRqLVDnisD62S_OWRuSSLGcFsrmUT5KjWBTt9zm84APMUOnRB4m2WABPLAN_) Don't see what you're looking for? See all available trips from Columbus to West Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-10/2025-11-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Mountain holidays in West 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 $1,066 per person Dec 28 - Dec 31 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 10/10 Exceptional! (2 reviews) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2025-12-31/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115163763&paandie=true&HotelClass=50&dealMarker=QpLfFRqLVDnisD62S_OWRuSSLGcFsrmUT5KjWBTt9zm84APMUOnRB4m2WABPLAN_) ![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 $1,518 per person Nov 26 - Nov 30 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Awesome room amazing tub even better service Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-26/2025-11-30/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=inO400m4vNsdT9Pocg7D8DtRhGxWu3f25J_-G_FYMRQWyro6wkNs_ZyZkjo5HLPQ) ![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 $1,175 per person Dec 17 - Dec 20 found 15 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-17/2025-12-20/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=VItR9I3dZmlQMbTWqB3yJhfB2mEY-bbqB_3gnmFHQji8y17WrhGy7PjSyJDlrIgn) Don't see what you're looking for? See all available trips from Columbus to West Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-10/2025-11-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Mountain holidays in West 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 $1,008 per person Dec 28 - Dec 31 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Awesome room amazing tub even better service Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2025-12-31/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=QpLfFRqLVDnisD62S_OWRoG19sPo-U_aU0pkZviyX5XoS_kYeFsFzTbSUrawGrMU) ![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 $1,066 per person Dec 28 - Dec 31 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 10/10 Exceptional! (2 reviews) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2025-12-31/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115163763&paandie=true&HotelClass=40&dealMarker=QpLfFRqLVDnisD62S_OWRuSSLGcFsrmUT5KjWBTt9zm84APMUOnRB4m2WABPLAN_) ![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 $1,175 per person Dec 17 - Dec 20 found 15 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-17/2025-12-20/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=VItR9I3dZmlQMbTWqB3yJhfB2mEY-bbqB_3gnmFHQji8y17WrhGy7PjSyJDlrIgn) Don't see what you're looking for? See all available trips from Columbus to West Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-10/2025-11-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Mountain holidays in West Side Price found within the past 48 hours. Click for updated prices. ![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 $706 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) The bed was extremly comfortable Staff was very attentive. Highly recommend Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRhj5KBURJ4dwaYsNvx6HEhQbJpw7mSJFfFv3NEd20zkK) ![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 $707 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (291 reviews) Food price was high but everything was fine Reviewed on Oct 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=8yRry5JRCnY_b9pY3eCEPyF_reVq0SC83JTyuLQqI4QulM3LF9oqGLTlWa0axRgd) ![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 $1,300 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Awesome room amazing tub even better service Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRmThmDVbnZKR8JLgsSfFKFav-_ObckwIVhcfCnR_PZLe) Don't see what you're looking for? See all available trips from Columbus to West Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-10/2025-11-17/?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 West Side](https://expedia.ca/Cheap-Flights-To-West-Side.d553248635976475400.Travel-Guide-Flights)[West Side Hotels](https://expedia.ca/West-Side-Hotels.d553248635976475400.Travel-Guide-Hotels)[West Side Vacation Rentals](https://expedia.ca/West-Side-Vacation-Rentals.d553248635976475400.Travel-Guide-VacationRentals)[West Side Car Rentals](https://expedia.ca/Car-Rentals-In-West-Side.d553248635976475400.Car-Rental-Guide)[West Side Vacations](https://expedia.ca/West-Side.d553248635976475400.Destination-Travel-Guides)[Things to do in West Side](https://expedia.ca/Things-To-Do-In-West-Side.d553248635976475400.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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)