Title: Southeast Wisconsin Vacation Packages & Trips 2026 from CA $586 | 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. ![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 $586 per person Mar 15 - Mar 18 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back! Reviewed on Jan 11, 2026 ![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 $1,053 per person Mar 15 - Mar 18 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Staff were impeccable.. greeted with small glass of champagne. Bed was comfortable, room was quiet. Would definitely stay here again.. Reviewed on Jan 11, 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $827 per person Mar 15 - Mar 18 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay. Reviewed on Jan 12, 2026 ![4BR Corporate Suite Central and Modern](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/0374aa13_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 4BR Corporate Suite Central and Modern Near North Side CA $1,329 per person Feb 27 - Mar 6 found 1 day ago Roundtrip flight included Calgary (YYC) to Chicago (ORD) 10/10 Exceptional! (8 reviews) Good for family, enjoyed the stay Reviewed on Dec 31, 2025 ![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 $896 per person Apr 2 - Apr 6 found 14 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (766 reviews) We absolutely love staying here! It’s fantastic every time!! Reviewed on Jan 4, 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) ![Milwaukee](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/219000/219557-Milwaukee.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) ![Milwaukee County Zoo which includes zoo animals and dangerous animals as well as a family](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/31000/31457-Milwaukee-County-Zoo.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 The Mayfair Collection 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) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.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) ![Milwaukee Public Library which includes interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/31000/31500-Milwaukee-Public-Library.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) ![Milwaukee Art Museum](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/219000/219539-Milwaukee.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) ## 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 $197 CA $233 total Jan 23 - Jan 24 includes taxes & fees 9.4/10 Exceptional! (1,864 reviews) This is a beautiful historic hotel with a number of wonderful amenities. Unfortunately, we had a few problems with food/drink orders being forgotten both in the Mason Street Grill and room service. The staff handled these situations well by providing free items in compensation. The hotel was also ... Reviewed on Jan 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F01%2F2026&endDate=24%2F01%2F2026&selected=19467&PinnedHotelID=19467&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 Fully refundableReserve now, pay when you stay CA $158 CA $186 total Jan 25 - Jan 26 includes taxes & fees 9.6/10 Exceptional! (2,520 reviews) Great staff, amenities and room. Everything was clean and professional Reviewed on Jan 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=23253&PinnedHotelID=23253&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) If it was possible to give this host and property more than five stars, we would! Mike was extremely responsive with any questions (even on Thanksgiving day!) and provided detailed and clear check in/check out instructions and misc. details about the property. The kids LOVED the kidquarium and game ... Reviewed on Nov 28, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=26%2F01%2F2026&endDate=27%2F01%2F2026&selected=67422248&PinnedHotelID=67422248&HadPinnedHotel=true®ionId=6059645) [](https://expedia.ca/Hotel-Search?startDate=26%2F01%2F2026&endDate=27%2F01%2F2026&selected=67422248&PinnedHotelID=67422248&HadPinnedHotel=true®ionId=6059645) [See all 2,340 properties in Southeast Wisconsin](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=13%2F01%2F2026&endDate=14%2F01%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://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54544-Harley-Davidson-Museum-Milwaukee.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://a.travel-assets.com/findyours-php/viewfinder/images/res70/219000/219540-Milwaukee.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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