Title: Southeast Wisconsin Vacation Packages & Trips 2026 from CA $707 | Expedia.ca [Southeast Wisconsin Travel Guide](https://expedia.ca/Southeast-Wisconsin.dx6059645)[Hotels in Southeast Wisconsin](https://expedia.ca/Southeast-Wisconsin-Hotels.d6059645.Travel-Guide-Hotels)[Vacation Rentals in Southeast Wisconsin](https://expedia.ca/Southeast-Wisconsin-Vacation-Rentals.d6059645.Travel-Guide-VacationRentals)[Flights to Southeast Wisconsin](https://expedia.ca/Cheap-Flights-To-Southeast-Wisconsin.d6059645.Travel-Guide-Flights)[Southeast Wisconsin Car Rentals](https://expedia.ca/Car-Rentals-In-Southeast-Wisconsin.d6059645.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6068277/1fe18a15-7f30-4ecc-8164-b72f9b7fcfed.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southeast Wisconsin Vacation Packages ## 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 ### Your Southeast Wisconsin Vacation Our Southeast Wisconsin vacation packages provide an affordable, easy and immersive way to enjoy everything this exciting destination has to offer. If it's distilleries and craft breweries and dining you're yearning for, this is the place to come. With so many things to see and do on a trip to Southeast Wisconsin, it can be tricky to know where to begin. Kick off your journey in [Milwaukee](https://www.expedia.ca/Milwaukee.d602647.Destination-Travel-Guides) at American Family Field and Wisconsin State Fair Park — two much-loved attractions here. Another top city worth adding to your itinerary is [Lake Geneva](https://www.expedia.ca/Lake-Geneva.d6046584.Destination-Travel-Guides). Be sure not to miss Geneva Lake and Walworth County Fairgrounds. Expedia has everything you need for planning your Southeast Wisconsin vacation. From accommodations and flights, to car rentals and activities, we know how to curate a travel experience like no other. ## Top Southeast Wisconsin Vacation Deals Price found within the past 48 hours. Click for updated prices. ![JW Marriott Chicago](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/232aa080_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### JW Marriott Chicago Downtown Chicago CA $707 per person May 1 - May 3 found 16 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.2/10 Wonderful! (1,000 reviews) Bottle of waters were not stocked in the refrigerator. Reviewed on Jan 6, 2026 ![La Banque Hotel](https://images.trvl-media.com/lodging/15000000/14710000/14702200/14702161/a8c9af9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Banque Hotel CA $743 per person Apr 9 - Apr 12 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (447 reviews) Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring. Reviewed on Jan 26, 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 $828 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included Montreal Metropolitan Airport (YHU) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Everything was amazing, specially the breakfast buffet. Reviewed on Feb 7, 2026 ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $708 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included Montreal Metropolitan Airport (YHU) to Chicago (ORD) 9/10 Wonderful! (766 reviews) Great stay. Would come again. Reviewed on Jan 19, 2026 ![Holiday Inn Club Vacations at Lake Geneva Resort by IHG](https://images.trvl-media.com/lodging/2000000/1690000/1681300/1681285/bf062b0f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Club Vacations at Lake Geneva Resort by IHG CA $723 per person Apr 21 - Apr 25 found 21 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 8.8/10 Excellent! (1,003 reviews) My room was very clean, which I appreciated. We booked a suite, but the first one opened directly into the bedroom, and being on the first floor, I didn’t feel comfortable with that layout. I requested a room change, and the staff handled it quickly and professionally, which I really appreciated. One thing that was a bit confusing was the inconsistency between suites—some had a full kitchen while others only had a range top. It would be helpful to know that in advance when booking. Overall, the stay was quiet and peaceful during the week, which was exactly what we wanted. When we arrived on Saturday afternoon, the atmosphere was completely different—lots of people, plenty of activity, and a lively environment. The only real downside was that the room felt drafty. We ended up putting a towel under the door to help block the cold air. Aside from those small issues, it was a comfortable stay with a good stay. Reviewed on Jan 16, 2026 ## Where to stay in Southeast Wisconsin Find the best Southeast Wisconsin areas and neighborhoods for the activities you enjoy most. [Learn more about Southeast Wisconsin](https://expedia.ca/Southeast-Wisconsin.dx6059645) ![Downtown skyline with Buildings along the Milwaukee River, in Milwaukee, Wisconsin.; Shutterstock ID 523595590](https://images.trvl-media.com/place/6059651/1182062a-a02d-493d-b9fe-49d298b5def0.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Milwaukee Central business district with cultural, financial, and historical landmarks, Downtown Milwaukee offers shopping at The Shops of Grand Avenue, art galleries in the Historic Third Ward, high-end dining, and vibrant nightlife. Explore the Milwaukee Public Market and Riverwalk, or hop on the free streetcar system. [Find hotel + flight trips in Downtown Milwaukee](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Milwaukee&DestID=6059651&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![96144781](https://images.trvl-media.com/place/6059657/3d426080-e9b2-426a-9651-cd836ecf4e89.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Wauwatosa Wauwatosa is known for its abundant dining options, and you can plan a trip to Mayfair Mall and AMF Bowlero Lanes while you're in town. [Find hotel + flight trips in Wauwatosa](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Wauwatosa&DestID=6059657&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Milwaukee Art Museum](https://images.trvl-media.com/place/6068277/f9df43ae-9037-4ed0-8755-204129016a40.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### East Town 4.5/5(18 area reviews) East Town is highly notable for its fantastic nightlife, and you might want to visit top sights like Lake Michigan and Veteran's Park. See more of Milwaukee by jumping on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop. [Find hotel + flight trips in East Town](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=East%20Town&DestID=6338567&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![The Milwaukee Riverwalk System began in 1993, as a means to offer public access to the river. Once complete, the Riverwalk will extend 3.1 miles along both sides of the Milwaukee River, from the site of the former North Avenue Dam, through Downtown and the Historic Third Ward to Lake Michigan. #LikeALocal](https://images.trvl-media.com/place/2325/e14aea82-f689-465b-a1de-58418a74a9ab.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Westown 2 out of top 10 points of interest in this area 4/5(8 area reviews) While visiting Westown, you might make a stop by sights like Miller High Life Theatre and Milwaukee Public Museum. [Find hotel + flight trips in Westown](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Westown&DestID=553248635976470851&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Ferris Wheel Spinning Round Illuminated in Night Sky](https://images.trvl-media.com/place/7685/c9ddb0cf-39d4-4515-b334-9d7a3f73ea61.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### West Allis West Allis is noteworthy for its restaurants, and you can make a stop at top attractions like Milwaukee Mile Speedway and Wisconsin State Fair Park. [Find hotel + flight trips in West Allis](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=West%20Allis&DestID=7685&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Ready to book your vacation to Southeast Wisconsin? Choose your dates ## Southeast Wisconsin Hotel Deals ![The Pfister Hotel](https://images.trvl-media.com/lodging/1000000/20000/19500/19467/169f18e6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Pfister Hotel 424 E Wisconsin Ave Milwaukee WI Fully refundableReserve now, pay when you stay CA $172 CA $203 total Mar 1 - Mar 2 includes taxes & fees 9.4/10 Exceptional! (1,927 reviews) We felt like royalty! Reviewed on Feb 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=19467&PinnedHotelID=19467&HadPinnedHotel=true®ionId=6059645) ![#EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms](https://images.trvl-media.com/lodging/68000000/67430000/67422300/67422248/469f0cf9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### #EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms Twin Lakes WI 10/10 Exceptional! (42 reviews) The house was perfect for a lovely family holiday! We had 11 adults, 4 kids, and 1 dog this year. There was plenty of room for everyone to have a great time. The house is stocked full of games and recreational areas (e.g., the kidquarium was a huge hit with our kids, as was the golf simulator). The ... Reviewed on Jan 2, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=67422248&PinnedHotelID=67422248&HadPinnedHotel=true®ionId=6059645) [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=67422248&PinnedHotelID=67422248&HadPinnedHotel=true®ionId=6059645) ![Saint Kate - The Arts Hotel](https://images.trvl-media.com/lodging/1000000/30000/23300/23253/63d91083_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Saint Kate - The Arts Hotel 139 E Kilbourn Ave Milwaukee WI CA $165 CA $195 total Feb 22 - Feb 23 includes taxes & fees 9.6/10 Exceptional! (2,550 reviews) Everything about our stay deserves 5 Stars....from the moment we walked in to the moment we left and everything in between. The staff people we interacted with were nothing short of pleasant & eager to help, the room was not only comfortable, but fun & unique and the art galleries added a special ... Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=23253&PinnedHotelID=23253&HadPinnedHotel=true®ionId=6059645) [See all 2,367 properties in Southeast Wisconsin](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®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. ![](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) ### Discover the most popular places to visit in Southeast Wisconsin ![Harley-Davidson Museum featuring interior views](https://images.trvl-media.com/place/6279040/52cab404-1cac-4be9-bd03-910682810f03.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Harley-Davidson Museum Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours. [](https://expedia.ca/Harley-Davidson-Museum-Menomonee-River-Valley.d6279040.Vacation-Attraction) ![Milwaukee Art Museum](https://images.trvl-media.com/place/6068277/1fe18a15-7f30-4ecc-8164-b72f9b7fcfed.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Milwaukee Art Museum Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building. [](https://expedia.ca/Milwaukee-Art-Museum-East-Town.d6068277.Vacation-Attraction) #### Potawatomi Bingo Casino Why not roll the dice with a visit to Potawatomi Bingo Casino during your time in Milwaukee? Attend a sporting event or simply enjoy the lively breweries while you're in the area. [](https://expedia.ca/Potawatomi-Bingo-Casino-Menomonee-River-Valley.d6335076.Vacation-Attraction) ## Frequently asked questions ### Can I cancel my flight booking to Southeast Wisconsin due to COVID-19? ### What's the best way to find cheap flights to Southeast Wisconsin that have flexible change policies? ### What are some of the general tips for travelers to Southeast Wisconsin during the COVID-19 outbreak? > - Find out if any travel restrictions apply to your destination and origin before booking anything. Also check if there are any special conditions you'll have to follow on arrival, such as proof of a negative COVID-19 test. > - Wear a face mask even during airport screening. A TSA officer will ask you to lower your mask temporarily for identification purposes. > - Instead of handing a TSA employee your boarding pass, position it directly on the scanner yourself. Then, hold it up for inspection. > - You're permitted to take one container of hand sanitizer up to 12 oz (350 ml) in your hand luggage. You'll need to remove it for X-ray screening. > - Remove items from your pocket, like your phone, keys and wallet, and place them in your carry-on rather than into bins. This will minimize handling during screening. > - If you want to take food on board, put it in a clear plastic bag and then into a screening bin. This reduces the likelihood that a TSA agent will need to touch your food container or carry-on bag for inspection. ### Which airlines fly to Southeast Wisconsin? ### How can I find cheap tickets to Southeast Wisconsin? ### How much is a flight to Southeast Wisconsin? ### What are the most popular airports to fly into in Southeast Wisconsin? ### When is the cheapest time to fly to Southeast Wisconsin? ### How much is a plane ticket to Southeast Wisconsin? ### Which airlines with flights to Southeast Wisconsin employ COVID-19 cleanliness policies? > - Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant. > - Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant. > - American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Luxury Hotels in Big Bend ](https://www.expedia.ca/Big-Bend-Hotels-Luxury-Hotel.0-0-d553248634983481436-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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