Title: Cheap Vacations in Southeast Wisconsin 2026 | Expedia.ca ![](https://images.trvl-media.com/place/6068277/1fe18a15-7f30-4ecc-8164-b72f9b7fcfed.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southeast Wisconsin Cheap 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 Cheap hotel deals in Southeast Wisconsin Price found within the past 48 hours. Click for updated prices. ![DoubleTree by Hilton Milwaukee - Brookfield](https://images.trvl-media.com/lodging/1000000/30000/26100/26053/fb600f8a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Milwaukee - Brookfield CA $917 per person Feb 20 - Feb 22 found 9 hours ago Roundtrip flight included Kelowna (YLW) to Milwaukee (MKE) 8.4/10 Very Good! (1,001 reviews) Breakfast was advertised as free but it was $15 Reviewed on Dec 7, 2025 ![The Iron Horse Hotel](https://images.trvl-media.com/lodging/3000000/2100000/2097200/2097106/2030b501_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Iron Horse Hotel Fifth Ward CA $1,524 per person Feb 25 - Mar 1 found 1 day ago Roundtrip flight included St. John's (YYT) to Milwaukee (MKE) 9.2/10 Wonderful! (1,008 reviews) Beautiful area. Beautiful hotel. Our room with a single king bed is not family friendly fyi. Glass shower walls so you can see through from the bed. Which is fine for couples but not with kids. Reviewed on Dec 8, 2025 ![The Ingleside Hotel](https://images.trvl-media.com/lodging/1000000/900000/894100/894006/8211d654_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ingleside Hotel CA $1,298 per person Feb 25 - Mar 1 found 1 day ago Roundtrip flight included St. John's (YYT) to Milwaukee (MKE) 8.6/10 Excellent! (748 reviews) I have stayed at this location several times and intend to return. However a bit disappointed that the room I initially selected was changed at the last minute. Another disappointment was the fact that there was no microwave available in the room. Reviewed on Dec 4, 2025 ![Saint Kate - The Arts Hotel](https://images.trvl-media.com/lodging/1000000/30000/23300/23253/63d91083_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Saint Kate - The Arts Hotel Downtown Milwaukee CA $1,062 per person Feb 20 - Feb 22 found 9 hours ago Roundtrip flight included Kelowna (YLW) to Milwaukee (MKE) 9.8/10 Exceptional! (2,425 reviews) Very fun artsy hotel in Milwaukee theater district. Good live music in the bar. An abundance of original art work on display. Very good restaurant. Reviewed on Dec 10, 2025 ![Hilton Milwaukee](https://images.trvl-media.com/lodging/1000000/10000/6100/6090/cc399a7a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Milwaukee Westown CA $1,085 per person Feb 20 - Feb 22 found 9 hours ago Roundtrip flight included Kelowna (YLW) to Milwaukee (MKE) 8.4/10 Very Good! (1,075 reviews) I really liked how nice the hotel looked. And the staff were very helpful. And I did enjoy playing with the doggies when they were around:) Reviewed on Dec 7, 2025 Don't see what you're looking for? See all available trips from Columbus to Southeast Wisconsin [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MKE&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Cheap holidays in Southeast Wisconsin Price found within the past 48 hours. Click for updated prices. ![DoubleTree by Hilton Milwaukee - Brookfield](https://images.trvl-media.com/lodging/1000000/30000/26100/26053/fb600f8a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Milwaukee - Brookfield CA $917 per person Feb 20 - Feb 22 found 9 hours ago Roundtrip flight included Kelowna (YLW) to Milwaukee (MKE) 8.4/10 Very Good! (1,001 reviews) Breakfast was advertised as free but it was $15 Reviewed on Dec 7, 2025 ![Saint Kate - The Arts Hotel](https://images.trvl-media.com/lodging/1000000/30000/23300/23253/63d91083_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Saint Kate - The Arts Hotel Downtown Milwaukee CA $1,062 per person Feb 20 - Feb 22 found 9 hours ago Roundtrip flight included Kelowna (YLW) to Milwaukee (MKE) 9.8/10 Exceptional! (2,425 reviews) Very fun artsy hotel in Milwaukee theater district. Good live music in the bar. An abundance of original art work on display. Very good restaurant. Reviewed on Dec 10, 2025 ![Hilton Milwaukee](https://images.trvl-media.com/lodging/1000000/10000/6100/6090/cc399a7a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Milwaukee Westown CA $1,085 per person Feb 20 - Feb 22 found 9 hours ago Roundtrip flight included Kelowna (YLW) to Milwaukee (MKE) 8.4/10 Very Good! (1,075 reviews) I really liked how nice the hotel looked. And the staff were very helpful. And I did enjoy playing with the doggies when they were around:) Reviewed on Dec 7, 2025 Don't see what you're looking for? See all available trips from Columbus to Southeast Wisconsin [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MKE&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Cheap holidays in Southeast Wisconsin Price found within the past 48 hours. Click for updated prices. ![DoubleTree by Hilton Milwaukee - Brookfield](https://images.trvl-media.com/lodging/1000000/30000/26100/26053/fb600f8a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Milwaukee - Brookfield CA $1,132 per person Feb 25 - Mar 1 found 1 day ago Roundtrip flight included St. John's (YYT) to Milwaukee (MKE) 8.4/10 Very Good! (1,001 reviews) Breakfast was advertised as free but it was $15 Reviewed on Dec 7, 2025 ![The Iron Horse Hotel](https://images.trvl-media.com/lodging/3000000/2100000/2097200/2097106/2030b501_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Iron Horse Hotel Fifth Ward CA $1,524 per person Feb 25 - Mar 1 found 1 day ago Roundtrip flight included St. John's (YYT) to Milwaukee (MKE) 9.2/10 Wonderful! (1,008 reviews) Beautiful area. Beautiful hotel. Our room with a single king bed is not family friendly fyi. Glass shower walls so you can see through from the bed. Which is fine for couples but not with kids. Reviewed on Dec 8, 2025 ![Hilton Milwaukee](https://images.trvl-media.com/lodging/1000000/10000/6100/6090/cc399a7a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Milwaukee Westown CA $1,577 per person Feb 25 - Mar 1 found 1 day ago Roundtrip flight included St. John's (YYT) to Milwaukee (MKE) 8.4/10 Very Good! (1,075 reviews) I really liked how nice the hotel looked. And the staff were very helpful. And I did enjoy playing with the doggies when they were around:) Reviewed on Dec 7, 2025 Don't see what you're looking for? See all available trips from Columbus to Southeast Wisconsin [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MKE&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Cheap Hotels in Southeast Wisconsin ![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 - 6 min drive from American Family Field 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! (2,005 reviews) Everything was great! Love the staff! Reviewed on Dec 8, 2025 [](https://expedia.ca/Milwaukee-Hotels-Drury-Plaza-Hotel-Milwaukee-Downtown.h32501737.Hotel-Information) ![Best Western Plus Milwaukee Airport Hotel & Conference Ctr](https://images.trvl-media.com/lodging/1000000/20000/11900/11861/9f1af6f1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Plus Milwaukee Airport Hotel & Conference Ctr 5105 S Howell Avenue Milwaukee WI - 14 min drive from American Family Field Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff ... 7.4/10 Good! (1,160 reviews) The room was very clean. It was very comfortable too. Staff were very helpfully, greeted me w/ courtesy, and overall very pleasant about taking care of us.!!! Reviewed on Dec 6, 2025 [](https://expedia.ca/Milwaukee-Hotels-Best-Western-Plus-Milwaukee-Airport-Hotel-Conference-Ctr.h11861.Hotel-Information) ![Sleep Inn & Suites Milwaukee Airport](https://images.trvl-media.com/lodging/3000000/2360000/2353100/2353060/831341c6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sleep Inn & Suites Milwaukee Airport 4600 S 6th St Milwaukee WI - 12 min drive from American Family Field Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ... 8.2/10 Very Good! (1,178 reviews) Not a fan of the breakfast selection but the hotel staff were very kind and the amenities were great especially the clean pool and hot tub Reviewed on Dec 8, 2025 [](https://expedia.ca/Milwaukee-Hotels-Sleep-Inn-Suites-Airport.h2353060.Hotel-Information) [See all 2,392 properties in Southeast Wisconsin](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6059645) 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 Southeast Wisconsin ](https://expedia.ca/Cheap-Flights-To-Southeast-Wisconsin.d6059645.Travel-Guide-Flights)[ Southeast Wisconsin Hotels ](https://expedia.ca/Southeast-Wisconsin-Hotels.d6059645.Travel-Guide-Hotels)[ Southeast Wisconsin Vacation Rentals ](https://expedia.ca/Southeast-Wisconsin-Vacation-Rentals.d6059645.Travel-Guide-VacationRentals)[ Southeast Wisconsin Car Rentals ](https://expedia.ca/Car-Rentals-In-Southeast-Wisconsin.d6059645.Car-Rental-Guide)[ Southeast Wisconsin Vacations ](https://expedia.ca/Southeast-Wisconsin.d6059645.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