Title: Cheap Vacations in Southern Wisconsin 2026 | Expedia.ca ![](https://images.trvl-media.com/place/2325/f29f5e3d-0eb0-45b8-94f1-06284f8af3d0.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southern Wisconsin Cheap Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Evae - ## 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 Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![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 $1,013 per person May 11 - May 15 found 22 hours ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) 10/10 makes you feel at home. One of the best hotels I’ve ever stayed in. Reviewed on Mar 23, 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 $1,190 per person Jun 4 - Jun 7 found 1 day ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) We loved everything about this modern hotel, with one exception: the room doors “bang” when closing. These sounds can be heard up and down the hall and woke us up multiple times. Recommendation to the property management to install some form of sound mitigation or softer closing mechanism in the doors. Reviewed on Mar 27, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,209 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. Reviewed on Mar 27, 2026 ![Hotel Arista](https://images.trvl-media.com/lodging/3000000/2150000/2141800/2141763/a6c36a1d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Arista CA $1,058 per person Jun 3 - Jun 9 found 17 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,011 reviews) Our room was spacious, clean and well appointed. I love a bathroom with good lighting and the tv in the vanity mirror was fantastic to catch the morning news as we got ready!! The staff was exceptional. From check in, to drinks at the bar, to room service, everyone was incredibly friendly and professional. I highly recommend Hotel Arista. Reviewed on Mar 24, 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 $1,773 per person May 18 - May 21 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Chicago (ORD) 9.8/10 Exceptional! (1,010 reviews) Wonderful, from the property to the staff, the food and the amenities. Will be staying again any time I travel to Chicago. Reviewed on Mar 25, 2026 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/2026-04-27/2026-05-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Cheap holidays in Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/a75a4abb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago CA $1,455 per person May 22 - May 25 found 23 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,006 reviews) Great location and property Reviewed on Mar 14, 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 $1,773 per person May 18 - May 21 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Chicago (ORD) 9.8/10 Exceptional! (1,010 reviews) Wonderful, from the property to the staff, the food and the amenities. Will be staying again any time I travel to Chicago. Reviewed on Mar 25, 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1ede47da_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,939 per person May 8 - May 12 found 17 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,007 reviews) Great place to stay . The staff was friendly and helpful !!! Reviewed on Mar 22, 2026 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/2026-04-27/2026-05-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Cheap holidays in Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![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 $1,190 per person Jun 4 - Jun 7 found 1 day ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) We loved everything about this modern hotel, with one exception: the room doors “bang” when closing. These sounds can be heard up and down the hall and woke us up multiple times. Recommendation to the property management to install some form of sound mitigation or softer closing mechanism in the doors. Reviewed on Mar 27, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,209 per person May 15 - May 18 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. Reviewed on Mar 27, 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 $1,277 per person Jun 4 - Jun 7 found 18 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) 10/10 makes you feel at home. One of the best hotels I’ve ever stayed in. Reviewed on Mar 23, 2026 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/2026-04-27/2026-05-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Cheap holidays in Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![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 $1,013 per person May 11 - May 15 found 22 hours ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) 10/10 makes you feel at home. One of the best hotels I’ve ever stayed in. Reviewed on Mar 23, 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 $1,253 per person May 4 - May 8 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) We loved everything about this modern hotel, with one exception: the room doors “bang” when closing. These sounds can be heard up and down the hall and woke us up multiple times. Recommendation to the property management to install some form of sound mitigation or softer closing mechanism in the doors. Reviewed on Mar 27, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,730 per person May 13 - May 17 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. Reviewed on Mar 27, 2026 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/2026-04-27/2026-05-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Cheap Hotels in Southern Wisconsin ![Natura Treescape Resort](https://images.trvl-media.com/lodging/18000000/17680000/17679300/17679264/9c3a04b2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Natura Treescape Resort 400 County Road A Wisconsin Dells WI - 2 hours drive from University of Wisconsin-Madison Book a stay at this beach hotel in Wisconsin Dells. Enjoy free WiFi, 2 indoor pools, and a private beach. Our guests praise the pool and the helpful staff in ... 8.2/10 Very Good! (1,140 reviews) It’s a great hotel for the price point. Considering it was the off season. Unfortunately our tv channels never worked and we couldn’t watch tv, but we spent little time in the room. Pool and hot tub were nice but the sauna didn't get hot. Staff were very nice and polite. Reviewed on Mar 24, 2026 [](https://expedia.ca/Wisconsin-Dells-Hotels-Natura-Treescape-Resort.h17679264.Hotel-Information) ![The Madison Concourse Hotel and Governor's Club](https://images.trvl-media.com/lodging/1000000/30000/28500/28447/5fd64d1f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Madison Concourse Hotel and Governor's Club 1 W Dayton St Madison WI - 5 min drive from University of Wisconsin-Madison Book a stay at this luxury hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the pool ... 9.4/10 Exceptional! (3,582 reviews) everything was better then expected. Reviewed on Mar 27, 2026 [](https://expedia.ca/Madison-Hotels-The-Madison-Concourse-Hotel-And-Governors-Club.h28447.Hotel-Information) ![Drury Plaza Hotel Milwaukee Downtown](https://images.trvl-media.com/lodging/33000000/32510000/32501800/32501737/ac1d9528_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Drury Plaza Hotel Milwaukee Downtown 700 N. Water Street Milwaukee WI - 3 hours drive from University of Wisconsin-Madison Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ... 9.6/10 Exceptional! (2,121 reviews) The staff at the hotel was the friendliest I have seen in a long time and the hotel room was superb Reviewed on Mar 27, 2026 [](https://expedia.ca/Milwaukee-Hotels-Drury-Plaza-Hotel-Milwaukee-Downtown.h32501737.Hotel-Information) [See all 7,435 properties in Southern Wisconsin](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248635975749457) 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 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