Title: Adventure Vacations in Southern Wisconsin 2025/2026 | Expedia.ca ![](https://images.trvl-media.com/place/6068277/f9df43ae-9037-4ed0-8755-204129016a40.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southern Wisconsin Adventure 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 Adventure hotel deals in Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Swissotel - Chicago Downtown Chicago CA $641 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9/10 Wonderful! (2,765 reviews) The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice Reviewed on Oct 9, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=17288&paandie=true&HotelClass=40&dealMarker=1qy9L2f9MnB3Zlaf3cNbvgzd4YdpHpN1rMXeNG-HcETeSj1XbthKiV0LZKalxgvb) ![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 $1,012 per person Dec 24 - Dec 29 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) 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/2025-12-24/2025-12-29/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&HotelClass=40&dealMarker=6CuNs0vxu2uILjtBFDt_O76dNQRhyY2vq896ZDtXkl3IfLl9JNXVowZEkFFGsrZg) ![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 $1,335 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Very clean very nice hotel. Easy accesss to restaurants and shopping. Reviewed on Oct 11, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=1qy9L2f9MnB3Zlaf3cNbvqHZNpbVMHi4Pi0elRppiT1TErA3SLcG-SiPE9GHALjI) ![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 $708 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) I loved the hotel, however I would request an inside room next time. It was extremely noisy outside. Reviewed on Oct 11, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=1qy9L2f9MnB3Zlaf3cNbvgzd4YdpHpN1rMXeNG-HcET0K1YZrTQnsbuixALC5Vl_) ![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 $1,346 per person Dec 26 - Dec 30 found 1 hour ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) We have stayed at every luxury property in Chicago and when coming to visit we always stay at the Park Hyatt. The rooms are spectacular! Reviewed on Oct 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2025-12-30/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=eg-fgMyrFK6DqGSHdw1Z49zZHgoGJALvWvvVenHWJNJpJyM9ffskkPxZr5vXnFL2) Don't see what you're looking for? See all available trips from Columbus to Southern Wisconsin [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-11/2025-11-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Adventure holidays in Southern Wisconsin 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 $1,335 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Very clean very nice hotel. Easy accesss to restaurants and shopping. Reviewed on Oct 11, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=1qy9L2f9MnB3Zlaf3cNbvqHZNpbVMHi4Pi0elRppiT1TErA3SLcG-SiPE9GHALjI) ![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 $1,346 per person Dec 26 - Dec 30 found 1 hour ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) We have stayed at every luxury property in Chicago and when coming to visit we always stay at the Park Hyatt. The rooms are spectacular! Reviewed on Oct 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2025-12-30/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=eg-fgMyrFK6DqGSHdw1Z49zZHgoGJALvWvvVenHWJNJpJyM9ffskkPxZr5vXnFL2) ![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 $1,565 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,002 reviews) Simply love this hotel Reviewed on Sep 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&HotelClass=50&dealMarker=n5HdZvsqH8RXHZEDY1p-0QNt3_7BIJ3ySTT_uelV4v8XY1LP80m_IOi6fIRaUeA2) Don't see what you're looking for? See all available trips from Columbus to Southern Wisconsin [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-11/2025-11-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Adventure holidays in Southern Wisconsin 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 $791 per person Nov 21 - Nov 24 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) I loved the hotel, however I would request an inside room next time. It was extremely noisy outside. Reviewed on Oct 11, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-21/2025-11-24/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=KH-gUp8pFW8rIIj7imVNQPK9V_sUT5f3RsuuUt80Vx8BjHMI2A1s3w5LyUwhEULW) ![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 $1,204 per person Dec 24 - Dec 27 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Very clean very nice hotel. Easy accesss to restaurants and shopping. Reviewed on Oct 11, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-24/2025-12-27/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=VItR9I3dZmlQMbTWqB3yJgLS_Fhn9s__GUixoJ4BMdSl5A24GIrc8UbQ3RI8_W4e) ![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 $1,432 per person Nov 22 - Nov 25 found 2 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,005 reviews) The staff is excellent. We always enjoy the club house and pool. Would recommend highly! Reviewed on Oct 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-25/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6309326&paandie=true&HotelClass=40&dealMarker=kj0YqkmLt6-agADzpv4pFOGGHwCga2TJ1J7D9gCEFJey6V1wa8XOApFjOt-qPvH6) Don't see what you're looking for? See all available trips from Columbus to Southern Wisconsin [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-11/2025-11-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Adventure holidays in Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![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 $604 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) 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/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=x1SjNoiayczajwoxNByBakv3U3vTJFZ_JUO0xpCfVCq7uWTGqhQ1FDPsXrPV0zVP) ![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 $1,335 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Very clean very nice hotel. Easy accesss to restaurants and shopping. Reviewed on Oct 11, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=1qy9L2f9MnB3Zlaf3cNbvqHZNpbVMHi4Pi0elRppiT1TErA3SLcG-SiPE9GHALjI) ![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 $708 per person Dec 15 - Dec 19 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) I loved the hotel, however I would request an inside room next time. It was extremely noisy outside. Reviewed on Oct 11, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-15/2025-12-19/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=1qy9L2f9MnB3Zlaf3cNbvgzd4YdpHpN1rMXeNG-HcET0K1YZrTQnsbuixALC5Vl_) Don't see what you're looking for? See all available trips from Columbus to Southern Wisconsin [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-11/2025-11-18/?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 Southern Wisconsin](https://expedia.ca/Cheap-Flights-To-Southern-Wisconsin.d553248635975749457.Travel-Guide-Flights)[Southern Wisconsin Hotels](https://expedia.ca/Southern-Wisconsin-Hotels.d553248635975749457.Travel-Guide-Hotels)[Southern Wisconsin Vacation Rentals](https://expedia.ca/Southern-Wisconsin-Vacation-Rentals.d553248635975749457.Travel-Guide-VacationRentals)[Southern Wisconsin Car Rentals](https://expedia.ca/Car-Rentals-In-Southern-Wisconsin.d553248635975749457.Car-Rental-Guide)[Southern Wisconsin Vacations](https://expedia.ca/Southern-Wisconsin.d553248635975749457.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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)