Title: Mountain Vacations in Far North Side 2026 | Expedia.ca ![](https://images.trvl-media.com/place/553248635074842747/4c830a7f-a9f5-4e29-83f7-dc2e54b474ac.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Far North Side Mountain Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by W. Ross Wells - ## 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 North Side Price found within the past 48 hours. Click for updated prices. ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $1,041 per person Jun 18 - Jun 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) Was a little noisy but I think that was just my unit. Facilities were top notch! Reviewed on Apr 4, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,156 per person Jun 18 - Jun 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Beautiful rooms at an amazing location. Parking is terribly expensive though, and breakfast is not included. There is no mini fridge, so good luck saving leftovers to reduce expenses. There is also no swimming pool which I found weird for a place this elegant. Their main restaurant does not have good breakfast. Go for dinner or lunch and you will be very happy. But don't bother with breakfast, it's just a bunch of cheese and grease and it's unpleasant. Reviewed on Apr 4, 2026 ![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 $1,284 per person May 23 - May 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,005 reviews) Great location and property Reviewed on Mar 14, 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1ede47da_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,471 per person May 23 - May 26 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,007 reviews) Great place to stay . The staff was friendly and helpful !!! Reviewed on Mar 22, 2026 ![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 $1,117 per person Jun 5 - Jun 7 found 17 hours ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (3,688 reviews) Clean , good location Reviewed on Apr 5, 2026 Don't see what you're looking for? See all available trips from Columbus to Far North Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-05/2026-05-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Mountain holidays in Far North 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 $1,284 per person May 23 - May 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,005 reviews) Great location and property Reviewed on Mar 14, 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1ede47da_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,471 per person May 23 - May 26 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,007 reviews) Great place to stay . The staff was friendly and helpful !!! Reviewed on Mar 22, 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,547 per person May 23 - May 26 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,852 reviews) Highly recommend a stay here! The staff are amazing and the restaurant is incredible; get the French toast. Reviewed on Apr 4, 2026 Don't see what you're looking for? See all available trips from Columbus to Far North Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-05/2026-05-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Mountain holidays in Far North Side Price found within the past 48 hours. Click for updated prices. ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/46b44b35_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $860 per person May 23 - May 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (876 reviews) Nice and clean. Great view. A few construction issues. Reviewed on Apr 4, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,156 per person Jun 18 - Jun 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Beautiful rooms at an amazing location. Parking is terribly expensive though, and breakfast is not included. There is no mini fridge, so good luck saving leftovers to reduce expenses. There is also no swimming pool which I found weird for a place this elegant. Their main restaurant does not have good breakfast. Go for dinner or lunch and you will be very happy. But don't bother with breakfast, it's just a bunch of cheese and grease and it's unpleasant. Reviewed on Apr 4, 2026 ![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 $1,284 per person May 23 - May 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,005 reviews) Great location and property Reviewed on Mar 14, 2026 Don't see what you're looking for? See all available trips from Columbus to Far North Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-05/2026-05-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Mountain holidays in Far North 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 $1,024 per person Jun 22 - Jun 26 found 18 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (3,688 reviews) Clean , good location Reviewed on Apr 5, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $1,090 per person Jun 22 - Jun 26 found 18 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) Was a little noisy but I think that was just my unit. Facilities were top notch! Reviewed on Apr 4, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,437 per person May 14 - May 18 found 16 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Beautiful rooms at an amazing location. Parking is terribly expensive though, and breakfast is not included. There is no mini fridge, so good luck saving leftovers to reduce expenses. There is also no swimming pool which I found weird for a place this elegant. Their main restaurant does not have good breakfast. Go for dinner or lunch and you will be very happy. But don't bother with breakfast, it's just a bunch of cheese and grease and it's unpleasant. Reviewed on Apr 4, 2026 Don't see what you're looking for? See all available trips from Columbus to Far North Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-05/2026-05-12/?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 North Side ](https://expedia.ca/Cheap-Flights-To-Far-North-Side.d553248635976475356.Travel-Guide-Flights)[ Far North Side Hotels ](https://expedia.ca/Far-North-Side-Hotels.d553248635976475356.Travel-Guide-Hotels)[ Far North Side Vacation Rentals ](https://expedia.ca/Far-North-Side-Vacation-Rentals.d553248635976475356.Travel-Guide-VacationRentals)[ Far North Side Car Rentals ](https://expedia.ca/Car-Rentals-In-Far-North-Side.d553248635976475356.Car-Rental-Guide)[ Far North Side Vacations ](https://expedia.ca/Far-North-Side.d553248635976475356.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. 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