Title: Cheap 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 Cheap 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 Cheap hotel deals in Northwest Side Price found within the past 48 hours. Click for updated prices. ![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 $986 per person Dec 22 - Dec 27 found 21 hours ago Roundtrip flight included Montreal (YUL) 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/2025-12-22/2025-12-27/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&HotelClass=40&dealMarker=b3fWbLscUsiTNf0BuuZUcMSXx-JLLBMi76ouIY8n2d9YHW1apD-jk1rEgcvIdZ34) ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $1,163 per person Nov 8 - Nov 14 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (698 reviews) Beautiful luxury condo. Didnt feel much like a hotel. Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-08/2025-11-14/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=74500458&paandie=true&HotelClass=40&dealMarker=si04vqpQeW4IVsaowpjJu-FWAigosyVm4j6ioN1YyzPg6Ve31xvRw4JroAwSLymA) ![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 $1,310 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Awesome room amazing tub even better service Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=kxd8HG-yLPB5tYMWska48EgT4i9Fd4tSXmLVscKX9LXLRo9OW5NhEowIQDa_qSBE) ![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 $1,106 per person Dec 26 - Dec 29 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses. Reviewed on Oct 6, 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=1723215&paandie=true&HotelClass=40&dealMarker=egSXX1dhV3zpRH99zFw0G2IG4Yi0XPVwBJOCBgF3q0VrGGWu9TiIUy6sp7TrTcIO) ![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 $1,270 per person Nov 8 - Nov 14 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 8.2/10 Very Good! (2,123 reviews) People were very nice and helpful. Room was adequate. The whole place just felt tired and old. The restaurant was a real throw back. The food was fine though. Reviewed on Oct 8, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-08/2025-11-14/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=8058&paandie=true&HotelClass=40&dealMarker=si04vqpQeW4IVsaowpjJu1w9jKso2WpU6wPpk_GKCh3ytEmxWzLa8zMvsXpx6Ws0) 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/2025-11-08/2025-11-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Cheap 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 $1,106 per person Dec 26 - Dec 29 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses. Reviewed on Oct 6, 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=1723215&paandie=true&HotelClass=50&dealMarker=egSXX1dhV3zpRH99zFw0G2IG4Yi0XPVwBJOCBgF3q0VrGGWu9TiIUy6sp7TrTcIO) ![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 $1,512 per person Nov 14 - Nov 18 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Awesome room amazing tub even better service Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-18/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=i0STOQOIokhg7XC8hkkZ1_dF87vgLlwmsLilrG-TwCuWO_3rxl8neVxffXRh6kpd) ![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 $1,835 per person Nov 14 - Nov 18 found 1 day ago Roundtrip flight included Toronto (YTZ) to Chicago (ORD) 9.8/10 Exceptional! (1,005 reviews) Everything was great. Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-18/?FromAirport=YTZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6309326&paandie=true&HotelClass=50&dealMarker=IKG3DGpTWJD8fJex3mKKl8EMD8cgziEVYW6CW2EQzQg1sqYdyk0HUNVuBli39Jxo) 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/2025-11-08/2025-11-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Cheap 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 $704 per person Dec 26 - Dec 29 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) The bed was extremly comfortable Staff was very attentive. Highly recommend Reviewed on Oct 7, 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=982552&paandie=true&HotelClass=40&dealMarker=egSXX1dhV3zpRH99zFw0GzbekSnTDAmtRUilUCjFsfWqGkV6UxwsWBIDchybZ0NH) ![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 $1,167 per person Nov 24 - Nov 27 found 1 day ago Roundtrip flight included Toronto (YTZ) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Awesome room amazing tub even better service Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-27/?FromAirport=YTZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=sFNmerZTMH9IBJjT7N-JIaKM3_uAUZX2Ba_g4uFBf1f1qXpA3IFVJMGBem4BQxo6) ![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 $1,106 per person Dec 26 - Dec 29 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses. Reviewed on Oct 6, 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=1723215&paandie=true&HotelClass=40&dealMarker=egSXX1dhV3zpRH99zFw0G2IG4Yi0XPVwBJOCBgF3q0VrGGWu9TiIUy6sp7TrTcIO) 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/2025-11-08/2025-11-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Cheap 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 $717 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) The bed was extremly comfortable Staff was very attentive. Highly recommend Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=kxd8HG-yLPB5tYMWska48C5bVEh4dNVihXkHyVztmm-Ti6aCfB12NNF8uubnXHbu) ![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 $1,310 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Awesome room amazing tub even better service Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=kxd8HG-yLPB5tYMWska48EgT4i9Fd4tSXmLVscKX9LXLRo9OW5NhEowIQDa_qSBE) ![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 $718 per person Dec 29 - Jan 2 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/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=OQQMP9SJzJr598QDfBadrBFS6S63pGmgPTkAwZsusLL8lwnHSR1jr05t5hvnZf_-) 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/2025-11-08/2025-11-15/?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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)