Title: Southeast Wisconsin Cheap Vacations 2026 | Expedia.com ![](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 Cheap Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 ## Top Cheap vacation packages in Southeast Wisconsin Price found within the past 48 hours. Click for updated prices. ![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 $396 per person May 22 - May 24 found 6 hours ago Roundtrip non-stop flight included Boston (BOS) to Milwaukee (MKE) 8.4/10 Very Good! (1,117 reviews) The Fitness Center is excellent with full sets of Dumbbells, plenty of Cardio options, Kettlebells, and mats. It’s very clean and open 24/7. Reviewed on Mar 2, 2026 ![Saint Kate - The Arts Hotel](https://images.trvl-media.com/lodging/1000000/30000/23300/23253/3a9f7f5d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Saint Kate - The Arts Hotel Downtown Milwaukee $656 per person Apr 8 - Apr 11 found 1 day ago Roundtrip non-stop flight included Syracuse (SYR) to Milwaukee (MKE) 9.8/10 Exceptional! (2,573 reviews) Clean room, nice staff, good location Reviewed on Mar 7, 2026 ![The Iron Horse Hotel](https://images.trvl-media.com/lodging/3000000/2100000/2097200/2097106/w1201h762x12y0-0e8e5e6d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Iron Horse Hotel Fifth Ward $871 per person May 15 - May 18 found 13 hours ago Roundtrip non-stop flight included Richmond (RIC) to Milwaukee (MKE) 9.2/10 Wonderful! (1,023 reviews) The hotel was beautiful. The lobby was very inviting and interesting. The room itself was gorgeous. I love the high ceilings and rustic look with all the exposed wood. The bed was very comfortable and the bathroom super clean and inviting. Reviewed on Mar 8, 2026 ![Ambassador Hotel Milwaukee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/120000/117100/117078/aab304bc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ambassador Hotel Milwaukee, Trademark Collection by Wyndham Marquette $437 per person May 13 - May 16 found 1 day ago Roundtrip flight included Boston (BOS) to Milwaukee (MKE) 9/10 Wonderful! (1,296 reviews) Beautiful! Very comfortable stay, and can't wait to visit again. Reviewed on Mar 3, 2026 ![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 $610 per person Apr 14 - Apr 16 found 5 hours ago Roundtrip non-stop flight included Evansville (EVV) to Milwaukee (MKE) 8.4/10 Very Good! (1,001 reviews) Clean room. Nice staff. Had to pay additional fee for the breakfast buffet. Reviewed on Mar 1, 2026 Don't see what you're looking for? See all available trips from Columbus to Southeast Wisconsin [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MKE&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Cheap vacations in Southeast Wisconsin Price found within the past 48 hours. Click for updated prices. ![Ambassador Hotel Milwaukee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/120000/117100/117078/aab304bc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ambassador Hotel Milwaukee, Trademark Collection by Wyndham Marquette $437 per person May 13 - May 16 found 1 day ago Roundtrip flight included Boston (BOS) to Milwaukee (MKE) 9/10 Wonderful! (1,296 reviews) Beautiful! Very comfortable stay, and can't wait to visit again. Reviewed on Mar 3, 2026 ![Saint Kate - The Arts Hotel](https://images.trvl-media.com/lodging/1000000/30000/23300/23253/3a9f7f5d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Saint Kate - The Arts Hotel Downtown Milwaukee $656 per person Apr 8 - Apr 11 found 1 day ago Roundtrip non-stop flight included Syracuse (SYR) to Milwaukee (MKE) 9.8/10 Exceptional! (2,573 reviews) Clean room, nice staff, good location Reviewed on Mar 7, 2026 ![The Iron Horse Hotel](https://images.trvl-media.com/lodging/3000000/2100000/2097200/2097106/w1201h762x12y0-0e8e5e6d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Iron Horse Hotel Fifth Ward $871 per person May 15 - May 18 found 13 hours ago Roundtrip non-stop flight included Richmond (RIC) to Milwaukee (MKE) 9.2/10 Wonderful! (1,023 reviews) The hotel was beautiful. The lobby was very inviting and interesting. The room itself was gorgeous. I love the high ceilings and rustic look with all the exposed wood. The bed was very comfortable and the bathroom super clean and inviting. Reviewed on Mar 8, 2026 Don't see what you're looking for? See all available trips from Columbus to Southeast Wisconsin [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MKE&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Cheap vacations in Southeast Wisconsin Price found within the past 48 hours. Click for updated prices. ![Lake Lawn Resort](https://images.trvl-media.com/lodging/1000000/40000/34500/34462/9418c1f6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lake Lawn Resort $362 per person Apr 9 - Apr 13 found 17 hours ago Roundtrip flight included New York (NYC) to Milwaukee (MKE) 9/10 Wonderful! (1,000 reviews) It’s not worth the resort fee during winter or really any time the pools, golf courses and tennis courts aren’t available. They shouldn’t charge in winter. Reviewed on Mar 8, 2026 ![Saint Kate - The Arts Hotel](https://images.trvl-media.com/lodging/1000000/30000/23300/23253/3a9f7f5d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Saint Kate - The Arts Hotel Downtown Milwaukee $793 per person May 14 - May 18 found 16 hours ago Roundtrip flight included Las Vegas (LAS) to Milwaukee (MKE) 9.8/10 Exceptional! (2,573 reviews) Clean room, nice staff, good location Reviewed on Mar 7, 2026 ![The Iron Horse Hotel](https://images.trvl-media.com/lodging/3000000/2100000/2097200/2097106/w1201h762x12y0-0e8e5e6d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Iron Horse Hotel Fifth Ward $744 per person May 19 - May 23 found 11 hours ago Roundtrip non-stop flight included Rapid City (RAP) to Milwaukee (MKE) 9.2/10 Wonderful! (1,023 reviews) The hotel was beautiful. The lobby was very inviting and interesting. The room itself was gorgeous. I love the high ceilings and rustic look with all the exposed wood. The bed was very comfortable and the bathroom super clean and inviting. Reviewed on Mar 8, 2026 Don't see what you're looking for? See all available trips from Columbus to Southeast Wisconsin [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MKE&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find amazing cheap vacations in Southeast Wisconsin #### How can I find budget-friendly Southeast Wisconsin vacation packages on Expedia? Playing around with the easy-to-use search wizard is one of the best ways to find affordable Southeast Wisconsin vacation packages on Expedia. Tap your dates in and it'll offer some of the cheapest Southeast Wisconsin getaways within seconds. You can also use the maximum price filter to view deals within your budget. If you're traveling during peak season dates, it's a good idea to book early to snag some of the best offers. You may score irresistible [last-minute specials](https://www.expedia.com/lp/b/vacations/last-minute-deals) for travel in low season. #### How to find cheap last-minute Southeast Wisconsin travel deals? On Expedia's [last-minute](https://www.expedia.com/lp/b/vacations/last-minute-deals) travel deals page, you'll encounter a plethora of special offers for late vacations to Southeast Wisconsin. Remember, you're more likely to bag savings on last-minute travel during off-peak periods. Consider checking different departure dates, too. Expedia's nifty search tool lets you compare some of the best last-minute Southeast Wisconsin vacation packages. The handy filters let you tailor your trip according to your preferences, including hotel star rating, amenities, and property location. #### When is the best time to visit Southeast Wisconsin on a budget? For some of the cheapest vacation packages to Southeast Wisconsin from $362, it's best to travel during low season dates. With fewer people traveling during these periods, flights and hotels usually have lower prices. It's also a good idea to avoid popular travel times. These include spring break, Thanksgiving, and other federal holidays. On Expedia, you'll encounter some of the best travel deals to Southeast Wisconsin. Best of all, vacation [payment plans](https://www.expedia.com/lp/b/vacations/planning) mean you can spread the cost of your trip over 3, 6, or 12 months. #### Can I cancel my Southeast Wisconsin vacation package booking? Yes, many of Expedia's cheap Southeast Wisconsin getaway packages allow for free cancellation in case your plans change. Follow the easy steps to cancel by logging into your Expedia account and clicking on “Trips” page'. Keep in mind, though, that each vacation package has different cancellation policies, so be sure to look over them before booking. The good news is you'll clearly see this information on Expedia when you book. There's even a free cancellation search filter that lets you view flexible vacations to Southeast Wisconsin. #### Why should I book my Southeast Wisconsin vacation with Expedia? A multitude of exclusive travel deals you won't find anywhere else is one of the top reasons to book your cheap Southeast Wisconsin vacation package with Expedia. And with one of the widest choices of flights and hotels available, you'll easily find the right trip for you. The handy search wizard and filters let you compare hundreds of great deals in seconds, too. It's not only the cheap prices either: Expedia's booking protection and 24/7 support give you peace of mind before and during your 2026 trip. #### How to find cheap Southeast Wisconsin vacation packages on Expedia? When searching for budget vacations to Southeast Wisconsin, look out for the green savings label. This indicates you've snagged a deal only available on Expedia. Another popular way of getting money off your 2026Southeast Wisconsin vacation is by joining [One Key](https://www.expedia.com/welcome-one-key). Expedia's amazing reward program gives you access to hundreds of member-only discounts on select hotels. Keep a look out for the blue savings label in the search results. Best of all, One Key is free to join. #### Why should I book a package to Southeast Wisconsin? You'll often snag package savings on your Southeast Wisconsin vacation when bundling together your flights and accommodation. Expedia even shows you how much you're saving by booking a package. It's not just cheaper prices, either. Packages often have more flexible booking conditions, meaning you're more likely to get a refund in case your 2026 plans change. While booking flights and hotels separately usually requires full payment, Southeast Wisconsin vacation packages often let you pay a small upfront deposit to confirm. #### How to plan a cheap vacation to Southeast Wisconsin? Settling on your dates is usually the first step to planning an affordable Southeast Wisconsin getaway. If you're traveling during peak season dates, it's a good idea to book your trip in advance. This way, you're more likely to bag early-bird deals. Don't rule out a [last-minute travel deal](https://www.expedia.com/lp/b/vacations/last-minute-deals) for low season dates, though. Once you've picked your dates, tap them into the search wizard to see some of the best Southeast Wisconsin vacation package deals. Hop over to Expedia's [vacation planning page](https://www.expedia.com/lp/b/vacations/planning) for more tips for your dream vacation. ## Top Cheap Southeast Wisconsin Hotels ![Sleep Inn & Suites Milwaukee Airport](https://images.trvl-media.com/lodging/3000000/2360000/2353100/2353060/4b0e52b1_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 ... 8.4/10 Very Good! (1,199 reviews) The room wasn’t that clean . There was mold in the corners of the hot tub. The pool room was very dirty. Paint was chipping looked a little rusty when we were in our room there was a dirty old ice bucket dirt all over the headboards and counters. Reviewed on Mar 8, 2026 [](https://expedia.com/Milwaukee-Hotels-Sleep-Inn-Suites-Airport.h2353060.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 ... 7.6/10 Good! (1,143 reviews) Staff was amazing Reviewed on Mar 7, 2026 [](https://expedia.com/Milwaukee-Hotels-Best-Western-Plus-Milwaukee-Airport-Hotel-Conference-Ctr.h11861.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 - 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! (2,109 reviews) Clean room. Friendly staff. Extra conveniences. Reviewed on Mar 9, 2026 [](https://expedia.com/Milwaukee-Hotels-Drury-Plaza-Hotel-Milwaukee-Downtown.h32501737.Hotel-Information) [See all 2,397 properties in Southeast Wisconsin](https://expedia.com/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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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Wisconsin ](https://expedia.com/Car-Rentals-In-Southeast-Wisconsin.d6059645.Car-Rental-Guide)[ Southeast Wisconsin Vacations ](https://expedia.com/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 even more - get up to 20% on select hotels 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