Title: Adventure Vacations in Illinois 2026 | Expedia.ca ![](https://images.trvl-media.com/place/215/aa920d34-e093-4af5-87ef-8a5ae8eefcac.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Illinois 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 Illinois 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 $656 per person May 7 - May 10 found 10 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 8.6/10 Excellent! (3,039 reviews) A beautiful historic hotel...we very much enjoyed our stay there. Reviewed on Mar 31, 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 $1,093 per person May 14 - May 17 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 8.8/10 Excellent! (1,575 reviews) Nice clean hotel. Enjoyed our stay Reviewed on Apr 2, 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 $1,968 per person May 4 - May 9 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (3,647 reviews) Had a great weekend! Reviewed on Apr 1, 2026 ![Chicago Athletic Association, a Hyatt Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/d313af43_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chicago Athletic Association, a Hyatt Hotel Downtown Chicago CA $1,970 per person May 4 - May 9 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9/10 Wonderful! (1,000 reviews) I hope to return! Clean, quiet rooms, great vibe and decor, excellent amenities, customer service, and food. I had a number of special requests and was repeatedly met with over-the-top fantastic service. Plus, what a great location! Reviewed on Mar 17, 2026 ![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 $1,536 per person May 13 - May 16 found 22 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,001 reviews) Service was wonderful! Hotel is very well located close to shops, restaurants and coffee shops. Lots to see and do around and hotel itself is pure luxury. We had a wonderful stay! Reviewed on Mar 27, 2026 Don't see what you're looking for? See all available trips from Columbus to Illinois [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-03/2026-05-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Adventure holidays in Illinois Price found within the past 48 hours. Click for updated prices. ![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 $918 per person May 8 - May 10 found 8 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Chicago (ORD) 9.2/10 Wonderful! (1,000 reviews) Enjoyed a very comfortable stay. Reviewed on Mar 30, 2026 ![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 $1,536 per person May 13 - May 16 found 22 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,001 reviews) Service was wonderful! Hotel is very well located close to shops, restaurants and coffee shops. Lots to see and do around and hotel itself is pure luxury. We had a wonderful stay! Reviewed on Mar 27, 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 $1,962 per person May 7 - May 10 found 10 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,010 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 Illinois [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-03/2026-05-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Adventure holidays in Illinois Price found within the past 48 hours. Click for updated prices. ![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 $689 per person May 7 - May 10 found 10 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (2,091 reviews) Had a fantastic stay at the Kinzie Hotel in Chicago! The location is perfect, but what really stood out was the exceptional service. The front desk team was warm, welcoming, and incredibly helpful throughout my stay. The happy hour reception was a great touch, and the breakfast servers were just as impressive—friendly, attentive, and genuinely caring. You can tell the staff takes pride in creating a great experience. Comfortable rooms, great atmosphere, and top-notch service all around. I would absolutely stay here again! Reviewed on Apr 3, 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 $817 per person May 7 - May 10 found 10 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,140 reviews) Staff really friendly and hotel was clean and close to everything around the city can’t wait to come back. Reviewed on Mar 23, 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 $1,093 per person May 14 - May 17 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 8.8/10 Excellent! (1,575 reviews) Nice clean hotel. Enjoyed our stay Reviewed on Apr 2, 2026 Don't see what you're looking for? See all available trips from Columbus to Illinois [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-03/2026-05-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Adventure holidays in Illinois 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 $916 per person May 7 - May 11 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 8.6/10 Excellent! (2,329 reviews) The hotel main lobby is so beautiful! The pool was great and warm for the cold weather. Everything is walking distance. Reviewed on Apr 3, 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 $2,068 per person May 25 - May 29 found 9 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.8/10 Exceptional! (1,010 reviews) Excellent room and facilities. Helpfull staff and amazing locstion. Reviewed on Mar 27, 2026 ![Hilton Garden Inn Chicago Downtown/Magnificent Mile](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/f36e2ebe_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile Downtown Chicago CA $1,164 per person May 17 - May 21 found 1 day ago Roundtrip flight included Detroit (DTT) to Chicago (ORD) 8.6/10 Excellent! (4,416 reviews) Did not see breakfast bar Reviewed on Apr 2, 2026 Don't see what you're looking for? See all available trips from Columbus to Illinois [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-03/2026-05-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Adventure Hotels in Illinois ![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 CA $256 CA $335 total Apr 26 - Apr 27 includes taxes & fees 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! (2,345 reviews) The hotel main lobby is so beautiful! The pool was great and warm for the cold weather. Everything is walking distance. Reviewed on Apr 3, 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 CA $274 CA $355 total Apr 26 - Apr 27 includes taxes & fees 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! (1,076 reviews) Place was nice as always. We always go for a convention. Room was newly renovated. Trhe bathroom light wouldnt stay on though. It was on a timer and if you were in the shower it would just click off and youd be lift in darkness. Staff was okay for the most part besides the bell hop. Husband tried ... Reviewed on Mar 30, 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 CA $280 CA $377 total Apr 5 - Apr 6 includes taxes & fees 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! (3,473 reviews) No complaints about the room or breakfast or bar or restaurant. Great view of the river and lake from our room. Enjoyed the convenient location. Reviewed on Mar 31, 2026 [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) [See all 10,566 properties in Illinois](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=215) 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 [Illinois Flights ](https://expedia.ca/Destinations-In-Illinois.d215.Flight-Destinations)[ Illinois Hotels ](https://expedia.ca/Destinations-In-Illinois.d215.Hotel-Destinations)[ Illinois Vacation Rentals ](https://expedia.ca/Destinations-In-Illinois.d215.Vacation-Rental-Destinations)[ Illinois Car Rentals ](https://expedia.ca/Destinations-In-Illinois.d215.Car-Rental-Destinations)[ Illinois Vacations ](https://expedia.ca/Illinois.d215.Destination-Travel-Guides)[ Things to do in Illinois ](https://expedia.ca/Things-To-Do-In-Illinois.d215.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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