Title: Adventure Vacations in Northwest Side 2026/2026 | Expedia.ca ![](https://images.trvl-media.com/place/829/2253d64b-0974-4770-85a9-32842b88f38f.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Northwest Side Adventure 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 Adventure hotel deals in Northwest 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 $500 per person Feb 12 - Feb 16 found 23 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) great staff...loved our stay. Reviewed on Nov 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&HotelClass=40&dealMarker=wfVl52Kb4qOSeVECiqdWnbqKsNpL1ny-urCWiHbFzlNS03pFBTuI6_xI3LIRBY94) ![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 $677 per person Feb 12 - Feb 16 found 23 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Its room was perfect the only bad part was their was a couple stains in the bathroom wall Reviewed on Dec 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&HotelClass=40&dealMarker=wfVl52Kb4qOSeVECiqdWnaaQCNt92NKB_aaqTF2zRY2fBOzsZB0DL9VTBSF0zsm-) ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $544 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in. Reviewed on Nov 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=95823687&paandie=true&HotelClass=40&dealMarker=2MaV768TBcz8HM99OhHJ6PaM6kiv_o683bUEtJS_hDfJAYGHbsvDbg5H5QoUiDaA) ![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 $733 per person Feb 13 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YYZ) 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 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-13/2026-02-16/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=qoEzt0-XoA-UCyz6JEB_knjuLZHfA7Q77b8bj280tI3YDavtwemrlFJ3oHl3duOk) ![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 $865 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.6/10 Exceptional! (1,000 reviews) It is always an amazing place to stay Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=2MaV768TBcz8HM99OhHJ6PaM6kiv_o683bUEtJS_hDdG9S3nQkdqCt-m88f3zohs) 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/2026-01-02/2026-01-09/?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 $865 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.6/10 Exceptional! (1,000 reviews) It is always an amazing place to stay Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=2MaV768TBcz8HM99OhHJ6PaM6kiv_o683bUEtJS_hDdG9S3nQkdqCt-m88f3zohs) ![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 $1,369 per person Feb 12 - Feb 16 found 20 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) The staff was amazing. Will be making a return stay. Reviewed on Nov 30, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&HotelClass=50&dealMarker=2MaV768TBcz8HM99OhHJ6IQPVwBG5pBO_gm6q2PUZHHsTsJLj_tWuhr5IJ0I0PwX) ![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 $1,093 per person Feb 27 - Mar 2 found 16 hours ago Roundtrip flight included Montreal (YUL) 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 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-27/2026-03-02/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=Iv3HNzwXsEvzE2M41LpVc2FSjdZH1g3kgtR-ml4sbtUuRgcAmcVUORzD1COitTOV) 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/2026-01-02/2026-01-09/?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. ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $544 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in. Reviewed on Nov 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=95823687&paandie=true&HotelClass=40&dealMarker=2MaV768TBcz8HM99OhHJ6PaM6kiv_o683bUEtJS_hDfJAYGHbsvDbg5H5QoUiDaA) ![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 $733 per person Feb 13 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YYZ) 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 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-13/2026-02-16/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=qoEzt0-XoA-UCyz6JEB_knjuLZHfA7Q77b8bj280tI3YDavtwemrlFJ3oHl3duOk) ![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 $865 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.6/10 Exceptional! (1,000 reviews) It is always an amazing place to stay Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=2MaV768TBcz8HM99OhHJ6PaM6kiv_o683bUEtJS_hDdG9S3nQkdqCt-m88f3zohs) 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/2026-01-02/2026-01-09/?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. ![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 $500 per person Feb 12 - Feb 16 found 23 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) great staff...loved our stay. Reviewed on Nov 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=wfVl52Kb4qOSeVECiqdWnbqKsNpL1ny-urCWiHbFzlNS03pFBTuI6_xI3LIRBY94) ![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 $677 per person Feb 12 - Feb 16 found 23 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Its room was perfect the only bad part was their was a couple stains in the bathroom wall Reviewed on Dec 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=wfVl52Kb4qOSeVECiqdWnaaQCNt92NKB_aaqTF2zRY2fBOzsZB0DL9VTBSF0zsm-) ![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 $720 per person Feb 12 - Feb 16 found 23 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (317 reviews) The room was beautiful and clean and a good city view of the city Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=wfVl52Kb4qOSeVECiqdWnaaQCNt92NKB_aaqTF2zRY3RMXlTc6QiQCbun6Z5cnLw) 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/2026-01-02/2026-01-09/?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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)