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. ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/46b44b35_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $767 per person May 7 - May 10 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (858 reviews) I would stay here again without a second thought. Great Reviewed on Mar 11, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $2,418 per person Jun 3 - Jun 9 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.2/10 Wonderful! (414 reviews) This place was amazing! We loved it so much we wanted to move in. It had everything we needed and was in the perfect area. Parker at the front desk was by far the best part of our stay, she was personable and welcoming and gave us the best costumer service we’ve ever experienced while being away! We will be back. Reviewed on Mar 8, 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 $1,281 per person Jun 4 - Jun 7 found 21 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Everyone that we encountered at the hotel was so helpful and so nice. Reviewed on Mar 11, 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago CA $2,248 per person Jun 3 - Jun 9 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (3,613 reviews) I thought the hotel was great. It has excellent views if you book a front facing room. The staff was really nice. I had an issue with my allergy to feathers. I had previously requested a room without feathers on the Expedia app, however it wasn’t forwarded to the Hotel. I told the Hotel about it, and they immediately had a room prepared for me and removed the feathers from it, but still left the bedding that was under the feather duvet cover and feather pillow, so I had a pretty bad allergic reaction the two days I was there. I don’t think I would’ve been able to stay a third. It was pretty disappointing, but I think if you don’t have a feather allergy at the hotel is a pretty great place. No other complaints or whatsoever other than this feather issue Reviewed on Mar 12, 2026 ![Staypineapple, An Iconic Hotel, The Loop](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/bbf9e380_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Staypineapple, An Iconic Hotel, The Loop Downtown Chicago CA $1,338 per person Jun 4 - Jun 7 found 21 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (1,016 reviews) Nice clean room with tons of historic charm. Love the duvets and view to Millennium Park Reviewed on Mar 9, 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/2026-04-12/2026-04-19/?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/c8149674_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $2,247 per person Apr 22 - Apr 26 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.6/10 Exceptional! (1,003 reviews) The room was a little dated. I was surprised that you didn’t have CNBC as a TV choice, I thought the gym was dated and the WiFi was inadequate Reviewed on Feb 28, 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $2,456 per person May 14 - May 18 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,844 reviews) One of the best hotels I've ever stayed at Reviewed on Mar 10, 2026 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/e294b3a4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $2,327 per person Apr 21 - Apr 25 found 8 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) This is an amazing hotel. From the facilities to the staff, the food and atmosphere and the intricacies of the room itself it’s an amazing property. In the heart of what used to be “The magnificent mile” it’s unimposing from the exterior but once you step inside the place is special. If you can afford it it’s probably the best hotel in Chicago. Do yourself a favor and splurge a little on a weekend trip. Chicago is a wonderful city for food and drinks. It’s seen better days but still a beautiful city. Reviewed on Mar 10, 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/2026-04-12/2026-04-19/?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 - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/46b44b35_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $767 per person May 7 - May 10 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (858 reviews) I would stay here again without a second thought. Great Reviewed on Mar 11, 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 $1,281 per person Jun 4 - Jun 7 found 21 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Everyone that we encountered at the hotel was so helpful and so nice. Reviewed on Mar 11, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $1,165 per person May 18 - May 21 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Chicago (ORD) 9.2/10 Wonderful! (414 reviews) This place was amazing! We loved it so much we wanted to move in. It had everything we needed and was in the perfect area. Parker at the front desk was by far the best part of our stay, she was personable and welcoming and gave us the best costumer service we’ve ever experienced while being away! We will be back. Reviewed on Mar 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/2026-04-12/2026-04-19/?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. ![Sports Illustrated Resorts Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/bc30a848_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sports Illustrated Resorts Chicago Downtown Chicago CA $868 per person May 7 - May 11 found 22 hours ago Roundtrip flight included Toronto (YTZ) to Chicago (ORD) 9.2/10 Wonderful! (1,407 reviews) Check in was quick and easy, room was clean and spacious Reviewed on Mar 9, 2026 ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/46b44b35_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $1,227 per person May 14 - May 18 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (858 reviews) I would stay here again without a second thought. Great Reviewed on Mar 11, 2026 ![Hyatt Place Chicago/Downtown - The Loop](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/57098577_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Place Chicago/Downtown - The Loop Downtown Chicago CA $1,395 per person May 14 - May 18 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.8/10 Excellent! (1,201 reviews) We flew all night and were very tired when we arrived at the property. We were so grateful to be able to check in early. Reviewed on Mar 9, 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/2026-04-12/2026-04-19/?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. 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