Title: Adventure Vacations in Northwest Side 2026 | Expedia.ca ![](https://images.trvl-media.com/place/553248635976475367/bfa3a438-7753-4d4b-b110-6e23898993ba.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. ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/7e178380_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Downtown Chicago CA $576 per person Apr 3 - Apr 5 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.6/10 Excellent! (2,008 reviews) The room was clean. The staff was very nice. They even held on to our stuff on our last day after check out so we could explore the town luggage free! Reviewed on Jan 23, 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 $638 per person Apr 3 - Apr 5 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Incredible location and wonderful satff Reviewed on Jan 23, 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 $1,275 per person Mar 26 - Mar 29 found 15 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Yes didn’t know you get free breakfast Reviewed on Jan 4, 2026 ![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 $698 per person Apr 3 - Apr 5 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Clean room and amenities Reviewed on Jan 8, 2026 ![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 $901 per person Apr 3 - Apr 5 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The room was boring thought it would be cleaner updated for the price best part was the view Reviewed on Jan 24, 2026 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/2026-02-24/2026-03-03/?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. ![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 $874 per person Mar 13 - Mar 15 found 15 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The room was boring thought it would be cleaner updated for the price best part was the view Reviewed on Jan 24, 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 $1,275 per person Mar 26 - Mar 29 found 15 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Yes didn’t know you get free breakfast Reviewed on Jan 4, 2026 ![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 $1,073 per person Apr 3 - Apr 5 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) First time there. Staff was helpful and they provided excellent memorable service Reviewed on Jan 20, 2026 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/2026-02-24/2026-03-03/?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. ![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 $616 per person Mar 27 - Mar 30 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Incredible location and wonderful satff Reviewed on Jan 23, 2026 ![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 $1,035 per person Mar 27 - Mar 30 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The room was boring thought it would be cleaner updated for the price best part was the view Reviewed on Jan 24, 2026 ![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 $783 per person Mar 27 - Mar 30 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Clean room and amenities Reviewed on Jan 8, 2026 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/2026-02-24/2026-03-03/?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. ![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 $885 per person Apr 2 - Apr 6 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Incredible location and wonderful satff Reviewed on Jan 23, 2026 ![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 $1,600 per person Apr 2 - Apr 6 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) First time there. Staff was helpful and they provided excellent memorable service Reviewed on Jan 20, 2026 ![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 $946 per person Apr 2 - Apr 6 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Property was clean, welcoming, pet friendly Reviewed on Jan 18, 2026 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/2026-02-24/2026-03-03/?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