Title: Mountain Vacations in Far Southwest 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) # Far Southwest 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 Far Southwest 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 $834 per person Dec 26 - Jan 2 found 22 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,004 reviews) Not big fan of the room amenities. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&HotelClass=40&dealMarker=1Jmr_eciIvxQfm858ExzdI7RjT8hiIMCsvS121Abg81jW93RtIxlvuixV6z98_Rr) ![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Michigan Avenue Chicago Downtown Chicago CA $1,071 per person Dec 21 - Dec 26 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 8.8/10 Excellent! (1,046 reviews) One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done. Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-21/2025-12-26/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&HotelClass=40&dealMarker=eQ41785sc6bOv5L8pbLHTvEhyvhROLawYa_LeRWnCRhqLgkhGAjr77uVvGavdR7Y) ![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 $1,038 per person Dec 26 - Jan 2 found 22 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly. Reviewed on Oct 16, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=1Jmr_eciIvxQfm858ExzdHKOvhybGoJa40MqfHcgXhBqSdKu6mvrc0Ve9cSNbTLa) ![Arlo Chicago](https://images.trvl-media.com/lodging/27000000/26920000/26910700/26910691/747fff56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arlo Chicago Downtown Chicago CA $871 per person Dec 26 - Jan 2 found 22 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,826 reviews) excellent hotel, the staff, access to the city. We had a nice time in Chicago Reviewed on Oct 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=26910691&paandie=true&HotelClass=40&dealMarker=1Jmr_eciIvxQfm858ExzdI7RjT8hiIMCsvS121Abg82OIWkwNgIl_sskm7xB-TKR) ![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 $1,034 per person Dec 26 - Jan 2 found 22 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,222 reviews) Staff friendly and convenient. However, a bit loud, like we were on the sidewalk hearing music, cars and trains. Room was very minimal and a bit stark. Most like a dorm room/hostel. Very low lighting, fine except to try to read at night. Reviewed on Oct 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=1Jmr_eciIvxQfm858ExzdHKOvhybGoJa40MqfHcgXhCc5xso_ol5wWaFD9SLzfJh) Don't see what you're looking for? See all available trips from Columbus to Far Southwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-17/2025-11-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Mountain holidays in Far Southwest Side Price found within the past 48 hours. Click for updated prices. ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago CA $1,176 per person Nov 26 - Nov 29 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,005 reviews) Excellent staff, check in process and dining experiences all superb! Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-26/2025-11-29/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6309326&paandie=true&HotelClass=50&dealMarker=PA3FMZb837eT9WkrMtHjEkAzsx3NmfjVe69jJzeHJjK5W0FIo8jJm8nG02EfjHxz) ![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 $1,706 per person Dec 21 - Dec 26 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel. Reviewed on Oct 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-21/2025-12-26/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=uVgFtQlYHnvz1XYkoNlmvFX0jcgmhi4HQn0_-lwSes1NrEjAFSmBXXiSj25lrja8) ![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 $1,363 per person Dec 23 - Dec 27 found 14 hours ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-27/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=o-gXl4B8HlDRTTvE1yGYl0JUNoh1kOoaV4A242dQEx9IQK_l_3-Q9snZ4A06rKg4) Don't see what you're looking for? See all available trips from Columbus to Far Southwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-17/2025-11-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Mountain holidays in Far Southwest 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 $613 per person Dec 12 - Dec 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,004 reviews) Not big fan of the room amenities. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-15/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&HotelClass=40&dealMarker=fGBlmbDjOackFL1GOo3VltgdNjBs4ELbgB37GlczzwQOVtIOcmahmsx6xVzZQJBC) ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago CA $1,176 per person Nov 26 - Nov 29 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,005 reviews) Excellent staff, check in process and dining experiences all superb! Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-26/2025-11-29/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6309326&paandie=true&HotelClass=40&dealMarker=PA3FMZb837eT9WkrMtHjEkAzsx3NmfjVe69jJzeHJjK5W0FIo8jJm8nG02EfjHxz) ![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 $657 per person Dec 12 - Dec 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly. Reviewed on Oct 16, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-15/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=fGBlmbDjOackFL1GOo3VltgdNjBs4ELbgB37GlczzwTIFX0tuFe2eyXZT8pqq3wJ) Don't see what you're looking for? See all available trips from Columbus to Far Southwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-17/2025-11-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Mountain holidays in Far Southwest Side Price found within the past 48 hours. Click for updated prices. ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $823 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Calgary (YYC) to Chicago (ORD) 9/10 Wonderful! (698 reviews) Great apartment in a very nice area of the city. Nice workout space and pool too. Clean and very comfy rooms! Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YYC&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=74500458&paandie=true&dealMarker=jLTYrGR6efIIdRzNb1L-RlPtxnupocDO8_Y1WuAEQBC_5fscSJ2gdyGeVnJu5XCe) ![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 $1,518 per person Nov 24 - Nov 28 found 16 hours ago Roundtrip non-stop flight included Toronto (YTZ) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel. Reviewed on Oct 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-28/?FromAirport=YTZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=xZoNbKkeuKvO5NyJjEe0_yn7n4jE950urPhoqq_E8TE0XtfjbpSFagNU1Am3o5_2) ![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 $1,363 per person Dec 23 - Dec 27 found 14 hours ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-27/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=o-gXl4B8HlDRTTvE1yGYl0JUNoh1kOoaV4A242dQEx9IQK_l_3-Q9snZ4A06rKg4) Don't see what you're looking for? See all available trips from Columbus to Far Southwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-17/2025-11-24/?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 Far Southwest Side](https://expedia.ca/Cheap-Flights-To-Far-Southwest-Side.d553248635976475353.Travel-Guide-Flights)[Far Southwest Side Hotels](https://expedia.ca/Far-Southwest-Side-Hotels.d553248635976475353.Travel-Guide-Hotels)[Far Southwest Side Vacation Rentals](https://expedia.ca/Far-Southwest-Side-Vacation-Rentals.d553248635976475353.Travel-Guide-VacationRentals)[Far Southwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Far-Southwest-Side.d553248635976475353.Car-Rental-Guide)[Far Southwest Side Vacations](https://expedia.ca/Far-Southwest-Side.d553248635976475353.Destination-Travel-Guides) \* 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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)