Title: All inclusive Vacations in Southern Wisconsin 2025/2026 | Expedia.ca ![](https://images.trvl-media.com/place/6068277/f9df43ae-9037-4ed0-8755-204129016a40.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southern Wisconsin All inclusive Vacations ## Book a Hotel + Flight or Car together to unlock savings Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## 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 All inclusive hotel deals in Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![Arlo Chicago](https://images.trvl-media.com/lodging/27000000/26920000/26910700/26910691/747fff56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arlo Chicago Downtown Chicago CA $609 per person Dec 4 - Dec 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,826 reviews) I wish that all the staff was more accommodating! some of them were some were not! Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-09/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=26910691&paandie=true&HotelClass=40&dealMarker=Eh8yZ7SVyG0I3TyvqNH-COfxCVPEMrD9sVV4OUymdgYnbnGw6kx2tnop0oHVfuR2) ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $821 per person Dec 4 - Dec 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) The bed was extremly comfortable Staff was very attentive. Highly recommend Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-09/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=Eh8yZ7SVyG0I3TyvqNH-CEfTIDK2SpU7DIHSAFfK6REVQ11QBk5E2guU4uPZOfAe) ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $827 per person Dec 4 - Dec 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,004 reviews) Clean room, friendly staff, great location and within walking distance from all shops! Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-09/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&HotelClass=40&dealMarker=Eh8yZ7SVyG0I3TyvqNH-CEfTIDK2SpU7DIHSAFfK6REWNWh5XwT9LBBejvofTkfE) ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago CA $860 per person Dec 4 - Dec 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,222 reviews) Perfect location and atmosphere Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-09/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=Eh8yZ7SVyG0I3TyvqNH-CM96U9cjRwhshhV-1p2X8jnYv_iUqtLGw8U8-N6-BX_Q) ![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 $649 per person Dec 4 - Dec 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,142 reviews) Absolutely loved this place.... views were great, staff was great, atmosphere was great! One of my most favorite places to stay. Reviewed on Oct 8, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-09/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=57651125&paandie=true&HotelClass=40&dealMarker=Eh8yZ7SVyG0I3TyvqNH-COfxCVPEMrD9sVV4OUymdgZsqag-eeLZkX4akiPkYmE9) 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/2025-11-09/2025-11-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* All inclusive holidays in Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![Art Villa ](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/a9b39b37_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Art Villa West Town CA $1,066 per person Dec 28 - Dec 31 found 20 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 10/10 Exceptional! (2 reviews) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2025-12-31/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115163763&paandie=true&HotelClass=50&dealMarker=QpLfFRqLVDnisD62S_OWRlKJwNaH5hVPXkxOjRejNxoNJMWPcqpU9g2xdPab_P7m) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $1,300 per person Dec 29 - Jan 2 found 20 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Awesome room amazing tub even better service Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=QpLfFRqLVDnisD62S_OWRmV35YwI2cvxWAhL192UHJZPrD042_VSWTur4HlaYv_Q) ![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 $1,471 per person Dec 24 - Dec 28 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-24/2025-12-28/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=i-scMYON3kKiMGO8VUu8-BXKlgm-39XLcYCpujddEEQ4PJRdbDQYOMNx5F4nq5Rd) 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/2025-11-09/2025-11-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night All inclusive holidays in Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $1,008 per person Dec 28 - Dec 31 found 20 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Awesome room amazing tub even better service Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2025-12-31/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=QpLfFRqLVDnisD62S_OWRlKJwNaH5hVPXkxOjRejNxre-auEgttE2RKi7O2ewrZm) ![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 $1,181 per person Nov 8 - Nov 11 found 4 hours ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-08/2025-11-11/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=inO400m4vNsdT9Pocg7D8LiCqmZZnoALoGqA47dxpmtfRUfNhaEX2iLnqVpEW2gR) ![Art Villa ](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/a9b39b37_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Art Villa West Town CA $1,066 per person Dec 28 - Dec 31 found 20 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 10/10 Exceptional! (2 reviews) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2025-12-31/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115163763&paandie=true&HotelClass=40&dealMarker=QpLfFRqLVDnisD62S_OWRlKJwNaH5hVPXkxOjRejNxoNJMWPcqpU9g2xdPab_P7m) 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/2025-11-09/2025-11-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night All inclusive holidays in Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $706 per person Dec 29 - Jan 2 found 20 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) The bed was extremly comfortable Staff was very attentive. Highly recommend Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRsNL45aXRMz_VDag6Ci8ph-kxmi_mo1Zbr_yxVNzzP8j) ![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Swissotel - Chicago Downtown Chicago CA $780 per person Nov 12 - Nov 16 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Chicago (ORD) 9/10 Wonderful! (2,765 reviews) The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice Reviewed on Oct 9, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-12/2025-11-16/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=17288&paandie=true&dealMarker=4KHtf_28eG-jw6YvmuAD3y5W1JBwT3Og6GTQ935B8n51OtB9Cu0POBVhHzqSdNUx) ![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 $1,310 per person Nov 12 - Nov 16 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-12/2025-11-16/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=4KHtf_28eG-jw6YvmuAD3xfO8nXV0wvglZuc3sumgsdP_1HRZ-W1fd8Q49OdhGgb) 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/2025-11-09/2025-11-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Embark on an unforgettable all-inclusive trip to Southern Wisconsin including airfare with Expedia #### What are some benefits of booking an all-inclusive vacation? When you opt for an all-inclusive vacation to Southern Wisconsin, you can have everything you want to do planned out in advance. That means you get to simply coast through your vacation knowing exactly what's coming next. Plus, this helps you get a final tally on the costs beforehand, so it's much easier on your budget. #### Can I book all-inclusive packages with airfare and meals? Yes, all-inclusive vacation packages are readily available for Southern Wisconsin, and you can search for them simply by using the search filter for all-inclusivity. When you book your flight along with your accommodations, you may even find some savings, with the potential to save up to 39. #### Why should I book Southern Wisconsin vacations that are all inclusive and adults only? Adults-only stays in Southern Wisconsin are good for travellers who are looking to relax in laid-back and easygoing surroundings. Everyone in the area will be looking to do much of the same without any kids to worry about, so you can truly take in some time for yourself in pampered bliss. Plus, you can filter for adults-only stays specifically in your search, so they're easy to find. #### Can I book all-inclusive packages? Yes, all-inclusive packages are fairly standard in Southern Wisconsin. You can easily find all-inclusive options by using the search filters, but that's just the beginning. If you're booking at the last minute, you may even find additional discounts as properties try to fill their last remaining spots for cheap vacations that are all inclusive. #### Can I book cheap all-inclusive trips to Southern Wisconsin? If you're looking to save, you'll find a wide range of prices available, ranging from CA $609. By booking your accommodations and flight together, you may be able to enjoy savings of up to 39. Be sure to sort your search results by price to list the cheapest options first. #### What should I look for when booking a 5-star all-inclusive vacation in Southern Wisconsin? If you've implemented the 5-star filter when searching for your all-inclusive vacation in Southern Wisconsin, there are a few factors to keep an eye out for. Spa access is particularly popular, as it's one of the best features you'll find in luxury accommodation options. Additionally, you should consider opting for an infinity pool and a luxury suite, especially if you're travelling with a relatively large group. #### What should I consider when booking Southern Wisconsin vacation packages that are all inclusive for the family? The most important thing to consider for all-inclusive family vacations to Southern Wisconsin is what your family is interested in. If your kids need access to a pool, you'll want to implement the search filter for that amenity. Kids' clubs can also be perfect for your family, as can babysitting services if the adults in your group plan on enjoying Southern Wisconsin's nightlife. #### How can I find the best deals on all-inclusive vacations in Southern Wisconsin? You can always sort your search results by price to automatically put the cheapest options at the top of your search while still considering all your implemented search filters. #### Can I book an all-inclusive package that is fully refundable? Yes, reservations that are fully refundable are available on some all-inclusive packages in . You can explore each package's cancellation policy in the policy section of their page, where you'll learn exactly how you can qualify. Sometimes, nothing is required to qualify. #### Why should I book an all-inclusive vacation with Expedia? Booking with Expedia makes it easy to find the ultimate all-inclusive vacation package. By offering accommodations and flights together, all-inclusive packages are easy for us to create and for you to enjoy. With benefits like being fully refundable and flexible dates on some packages, you can enjoy a more stree-free booking process. Expedia Rewards members can take that even further with the possibility of additional discounts. ## 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) ### Top All inclusive Vacation Destinations > - 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[All inclusive vacations in Sosúa](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/601998/Sosua) > - [All inclusive vacations in the Dominican Republic](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/50/Dominican-Republic) ## 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. 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