Title: Mountain Vacations in Far Southeast Side 2026/2026 | Expedia.ca ![](https://images.trvl-media.com/place/829/b4cf8e95-0f92-4795-af28-19f97bbf7dad.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Far Southeast Side Mountain Vacations ## Book a Hotel + Flight or Car together to unlock savings - ## 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 Southeast Side Price found within the past 48 hours. Click for updated prices. ![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Swissotel - Chicago Downtown Chicago CA $643 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (2,947 reviews) Amazing view, service was outstanding!! Simona was above and beyond! Best place to stay in Chicago and I have stayed at many! Secret little nook back there! Reviewed on Dec 2, 2025 ![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 $948 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay. Reviewed on Nov 26, 2025 ![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 $716 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views. Reviewed on Dec 3, 2025 ![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 $1,443 per person Jan 29 - Feb 3 found 18 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It's always perfection at the Trump. King suite with Lake view is the ultimate Reviewed on Dec 2, 2025 ![Chicago Athletic Association, a Hyatt Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/6b24bc12_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chicago Athletic Association, a Hyatt Hotel Downtown Chicago CA $937 per person Jan 29 - Feb 3 found 18 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9/10 Wonderful! (1,002 reviews) The Chicago Athletic Association Hotel is the most charming hotel in the city of Chicago. My wife and I recently got married in Chicago and one of the highlights of the weekend was hanging out at the hotel! It has a roaring 20's vibe with the dark woods in the main lobby and the large game room which is a fun place to get a drink and play chess/pool. Amazing location close to the Amtrak, Chicago subway, and the South shore railroad. And it's across the street from Millennium Park. Most importantly, the staff is very professional and attentive and will go above and beyond to make your stay perfect. I always stay at this hotel when I go to Chicago because of it's charm and service. I would never stay anywhere else because it's a truly unique hotel in an awesome location with the nicest and most professional staff. 10/10 recommend to anyone! Reviewed on Nov 20, 2025 Don't see what you're looking for? See all available trips from Columbus to Far Southeast Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Mountain holidays in Far Southeast Side Price found within the past 48 hours. Click for updated prices. ![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 $1,640 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Excellent service throughout the hotel Reviewed on Nov 29, 2025 ![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 $1,686 per person Feb 14 - Feb 20 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It's always perfection at the Trump. King suite with Lake view is the ultimate Reviewed on Dec 2, 2025 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,976 per person Jan 29 - Feb 3 found 18 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Absolutely fantastic hotel great service, you couldn’t ask for more. Reviewed on Dec 3, 2025 Don't see what you're looking for? See all available trips from Columbus to Far Southeast Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Mountain holidays in Far Southeast Side Price found within the past 48 hours. Click for updated prices. ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago O'Hare Airport O'Hare CA $619 per person Feb 13 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 8.2/10 Very Good! (2,158 reviews) Slept so good I missed my flight Reviewed on Dec 4, 2025 ![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 $1,178 per person Feb 12 - Feb 15 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.6/10 Exceptional! (1,000 reviews) It is always an amazing place to stay Reviewed on Nov 26, 2025 ![Art Villa ](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/00656023_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Art Villa West Town CA $1,161 per person Jan 21 - Jan 24 found 23 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 10/10 Exceptional! (2 reviews) Don't see what you're looking for? See all available trips from Columbus to Far Southeast Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Mountain holidays in Far Southeast Side Price found within the past 48 hours. Click for updated prices. ![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 $716 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views. Reviewed on Dec 3, 2025 ![Art Villa ](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/00656023_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Art Villa West Town CA $1,221 per person Jan 21 - Jan 25 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 10/10 Exceptional! (2 reviews) ![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 $948 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay. Reviewed on Nov 26, 2025 Don't see what you're looking for? See all available trips from Columbus to Far Southeast Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-05/2026-01-12/?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 Southeast Side ](https://expedia.ca/Cheap-Flights-To-Far-Southeast-Side.d553248635976475411.Travel-Guide-Flights)[ Far Southeast Side Hotels ](https://expedia.ca/Far-Southeast-Side-Hotels.d553248635976475411.Travel-Guide-Hotels)[ Far Southeast Side Vacation Rentals ](https://expedia.ca/Far-Southeast-Side-Vacation-Rentals.d553248635976475411.Travel-Guide-VacationRentals)[ Far Southeast Side Car Rentals ](https://expedia.ca/Car-Rentals-In-Far-Southeast-Side.d553248635976475411.Car-Rental-Guide)[ Far Southeast Side Vacations ](https://expedia.ca/Far-Southeast-Side.d553248635976475411.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. 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