Title: Adventure Vacations in Chicago 2026 | Expedia.ca ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chicago 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 Chicago Price found within the past 48 hours. Click for updated prices. ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Palmer House a Hilton Hotel Downtown Chicago CA $683 per person May 9 - May 12 found 1 day ago Roundtrip non-stop flight included Toronto (YTZ) to Chicago (ORD) 8.6/10 Excellent! (2,344 reviews) We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff. Reviewed on Apr 8, 2026 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $806 per person May 9 - May 12 found 1 day ago Roundtrip non-stop flight included Toronto (YTZ) to Chicago (ORD) 9.2/10 Wonderful! (1,123 reviews) The staff at the Pendry are top notch. We arrived early and just wanted to drop our bags off, but the staff was able to check us in several hours early. Upon learning it was my birthday, the bell hop brought me a glass of wine from the bar and later, the staff sent up a bottle of prosecco and birthday cupcakes. Our room Reviewed on Apr 7, 2026 ![Hotel 55 Chicago Downtown](https://images.trvl-media.com/lodging/1000000/30000/26800/26728/w4000h2662x0y0-b6434af4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel 55 Chicago Downtown Downtown Chicago CA $1,098 per person May 14 - May 17 found 3 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.8/10 Excellent! (1,575 reviews) The location is walking distance to a lot of stores and attractions. My room was clean, and the courteous staff were attentive to my needs. Reviewed on Apr 6, 2026 ![Kinzie Hotel](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/6044b661_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kinzie Hotel Downtown Chicago CA $913 per person Jun 10 - Jun 13 found 2 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.2/10 Wonderful! (2,090 reviews) Everything was great, the location the room at the shower water pressure was absolutely terrible Reviewed on Apr 7, 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 $1,158 per person Jun 10 - Jun 13 found 2 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.4/10 Exceptional! (3,647 reviews) Very nice and clean hotel Reviewed on Apr 8, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-09/2026-05-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Adventure holidays in Chicago Price found within the past 48 hours. Click for updated prices. ![Four Seasons Hotel Chicago](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/e5b56b9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Four Seasons Hotel Chicago Downtown Chicago CA $1,630 per person Jun 10 - Jun 13 found 2 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.4/10 Exceptional! (1,001 reviews) Beautiful and in walking distance to so many shops and cafes! We had a great stay. Reviewed on Apr 6, 2026 ![The Ritz-Carlton, Chicago](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/29a217ee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton, Chicago Downtown Chicago CA $1,827 per person May 13 - May 16 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.2/10 Wonderful! (1,000 reviews) Enjoyed a very comfortable stay. Reviewed on Mar 30, 2026 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $3,571 per person Jun 17 - Jun 21 found 24 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.8/10 Exceptional! (1,007 reviews) Excellent room and facilities. Helpfull staff and amazing locstion. Reviewed on Mar 27, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-09/2026-05-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Adventure holidays in Chicago Price found within the past 48 hours. Click for updated prices. ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $806 per person May 9 - May 12 found 1 day ago Roundtrip non-stop flight included Toronto (YTZ) to Chicago (ORD) 9.2/10 Wonderful! (1,123 reviews) The staff at the Pendry are top notch. We arrived early and just wanted to drop our bags off, but the staff was able to check us in several hours early. Upon learning it was my birthday, the bell hop brought me a glass of wine from the bar and later, the staff sent up a bottle of prosecco and birthday cupcakes. Our room Reviewed on Apr 7, 2026 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $1,749 per person May 18 - May 21 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Chicago (ORD) 9.8/10 Exceptional! (1,007 reviews) Excellent room and facilities. Helpfull staff and amazing locstion. Reviewed on Mar 27, 2026 ![Hotel 55 Chicago Downtown](https://images.trvl-media.com/lodging/1000000/30000/26800/26728/w4000h2662x0y0-b6434af4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel 55 Chicago Downtown Downtown Chicago CA $1,098 per person May 14 - May 17 found 3 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.8/10 Excellent! (1,575 reviews) The location is walking distance to a lot of stores and attractions. My room was clean, and the courteous staff were attentive to my needs. Reviewed on Apr 6, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-09/2026-05-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Adventure holidays in Chicago Price found within the past 48 hours. Click for updated prices. ![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/34f4da65_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Warwick Allerton - Chicago Downtown Chicago CA $1,461 per person May 13 - May 17 found 24 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 8.6/10 Excellent! (3,032 reviews) Warwick Allerton is my favorite place to stay when visiting Chicago! Staying in the Gold Coast means walking distance from the restaurants, stores and other Chicago touristy things. Super close to Nordstrom, Tiffany, Ralph Lauren etc. 5 minute walk to Steak 48 for dinner & about a 15 minute walk to the Navy Pier! A Walgreens is also close by for any last minute needs or touristy things like magnets and keychains. This hotel was also very accommodating, clean and had super kind staff. Parking is simple.. either use valet at the hotel or the hotel next door’s parking garage! Reviewed on Apr 7, 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 $1,545 per person Jun 18 - Jun 22 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (3,647 reviews) Very nice and clean hotel Reviewed on Apr 8, 2026 ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Palmer House a Hilton Hotel Downtown Chicago CA $1,670 per person May 13 - May 17 found 24 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 8.6/10 Excellent! (2,344 reviews) We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff. Reviewed on Apr 8, 2026 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-09/2026-05-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Adventure Hotels in Chicago ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Palmer House a Hilton Hotel 17 E Monroe St Chicago IL - 12 min drive from Wrigley Field Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ... 8.6/10 Excellent! (2,369 reviews) We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff. Reviewed on Apr 8, 2026 [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Hyatt Regency McCormick Place Chicago ](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/bc1f3373_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency McCormick Place Chicago 2233 S Martin Luther King Dr Chicago IL - 17 min drive from Wrigley Field Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ... 9.2/10 Wonderful! (1,075 reviews) Room newly renovated and beautiful. Reviewed on Apr 6, 2026 [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-McCormick-Place.h84736.Hotel-Information) ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3840h2559x0y3-c577bf94_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency Chicago 151 East Wacker Dr Chicago IL - 11 min drive from Wrigley Field Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ... 9.4/10 Exceptional! (3,485 reviews) Although location, lobby and stuff was good the newly updated rooms at the West tower were dirty and poorly taken care of. I found condiment packages behind the sink, mold in the sink, crumbs, and chocolate on the carpet floor and the blood on the bathroom wall, not to mention a very foul odor in ... Reviewed on Apr 7, 2026 [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) [See all 5,628 properties in Chicago](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=178248) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ## 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 Chicago ](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[ Chicago Hotels ](https://expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels)[ Chicago Vacation Rentals ](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[ Chicago Car Rentals ](https://expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide)[ Chicago Vacations ](https://expedia.ca/Chicago.d178248.Destination-Travel-Guides)[ Things to do in Chicago ](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities) \* 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