Title: Adventure Vacations in Northwest 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) # Northwest Side Adventure 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 Adventure hotel deals in Northwest Side Price found within the past 48 hours. Click for updated prices. ![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 $500 per person Nov 22 - Nov 25 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,826 reviews) Clean, nice, good location. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-25/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=26910691&paandie=true&HotelClass=40&dealMarker=xWUnHMKd-7lgW89xzilfj_Khuce4pGHET6f1J8Qv83nLwJ2q96ntUytmd5iClxuu) ![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 $850 per person Dec 23 - Dec 27 found 1 day ago Roundtrip flight included Toronto (YTO) 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/2025-12-23/2025-12-27/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&HotelClass=40&dealMarker=rF3q3WsoxfZMM53Mx3365U74lejmYh_w3n0wh43IXq9mY3Yg9SwPOBL3uE7YF7Kn) ![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 $1,336 per person Dec 23 - Dec 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Everything was great Reviewed on Oct 12, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-27/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=2U0YZgHH9wKpNZTA6CIVte_mkDibXXUBTbNi5wZuzEvP2KMk4r6X-CY_GLTowKZW) ![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 $574 per person Nov 22 - Nov 25 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) I loved the hotel, however I would request an inside room next time. It was extremely noisy outside. Reviewed on Oct 11, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-25/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=xWUnHMKd-7lgW89xzilfjx9jWpgBFwoGiBs6nTBiFsv3PolJ606T1ED2AhIpZvx3) ![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 $583 per person Nov 22 - Nov 25 found 1 day ago Roundtrip non-stop 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/2025-11-22/2025-11-25/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=xWUnHMKd-7lgW89xzilfj5iaFaFCcDoVbjBDzk1PNHksHaNk-vS-WthrfTbO3aUh) Don't see what you're looking for? See all available trips from Columbus to Northwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-21/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Adventure holidays in Northwest 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 $1,092 per person Dec 26 - Dec 29 found 1 day ago Roundtrip flight included Toronto (YTO) 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/2025-12-26/2025-12-29/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=OWBfzzOkUIZbu4Q2F5nRpF2gs8H7ZYAQZVjxcUZ3-Ooc2Gmj8iQYeVxVYBkygLKP) ![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 $1,336 per person Dec 23 - Dec 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Everything was great Reviewed on Oct 12, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-27/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=2U0YZgHH9wKpNZTA6CIVte_mkDibXXUBTbNi5wZuzEvP2KMk4r6X-CY_GLTowKZW) ![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 $1,535 per person Nov 28 - Dec 1 found 15 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,002 reviews) This is a very nice hotel. The staff is super accommodating. The location is one of the best in the area for shopping and dining. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-28/2025-12-01/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&HotelClass=50&dealMarker=t-s0udwzxCZ1aB60bCslRG6zrORFvQ3EbR8GBsS5w9oCqZtmIQT4S9Dp8lF6z1o1) Don't see what you're looking for? See all available trips from Columbus to Northwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-21/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Adventure holidays in Northwest 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 $574 per person Nov 22 - Nov 25 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) I loved the hotel, however I would request an inside room next time. It was extremely noisy outside. Reviewed on Oct 11, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-25/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=xWUnHMKd-7lgW89xzilfjx9jWpgBFwoGiBs6nTBiFsv3PolJ606T1ED2AhIpZvx3) ![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 $1,399 per person Nov 28 - Dec 1 found 15 hours ago Roundtrip non-stop flight included Toronto (YTO) 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/2025-11-28/2025-12-01/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=t-s0udwzxCZ1aB60bCslRMmJZEziyCcsXMJgNeV9okBn32I_tdxlfNmiCCUoYqhD) ![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 $1,155 per person Nov 13 - Nov 16 found 11 hours ago Roundtrip flight included Toronto (YTZ) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Everything was great Reviewed on Oct 12, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-13/2025-11-16/?FromAirport=YTZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=P4s7Hbaa8Nha_LtxlR1gc-e3TlPbUSk8PwrvagD9xH0wY0wSM3ce7flpy-79JMvV) Don't see what you're looking for? See all available trips from Columbus to Northwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-21/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Adventure holidays in Northwest Side Price found within the past 48 hours. Click for updated prices. ![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 $715 per person Dec 23 - Dec 27 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/2025-12-23/2025-12-27/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=rF3q3WsoxfZMM53Mx3365TT59rNOGOSV1l3UT3KPTXMpBQW1UxQhbC1F6TK2PBXT) ![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 $850 per person Dec 23 - Dec 27 found 1 day ago Roundtrip flight included Toronto (YTO) 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/2025-12-23/2025-12-27/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=rF3q3WsoxfZMM53Mx3365U74lejmYh_w3n0wh43IXq9mY3Yg9SwPOBL3uE7YF7Kn) ![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 $1,336 per person Dec 23 - Dec 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Everything was great Reviewed on Oct 12, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-27/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=2U0YZgHH9wKpNZTA6CIVte_mkDibXXUBTbNi5wZuzEvP2KMk4r6X-CY_GLTowKZW) Don't see what you're looking for? See all available trips from Columbus to Northwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-21/?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 Northwest Side](https://expedia.ca/Cheap-Flights-To-Northwest-Side.d553248635976475367.Travel-Guide-Flights)[Northwest Side Hotels](https://expedia.ca/Northwest-Side-Hotels.d553248635976475367.Travel-Guide-Hotels)[Northwest Side Vacation Rentals](https://expedia.ca/Northwest-Side-Vacation-Rentals.d553248635976475367.Travel-Guide-VacationRentals)[Northwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Northwest-Side.d553248635976475367.Car-Rental-Guide)[Northwest Side Vacations](https://expedia.ca/Northwest-Side.d553248635976475367.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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)