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. ![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 $424 per person Jan 17 - Jan 20 found 23 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9/10 Wonderful! (1,011 reviews) Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&HotelClass=40&dealMarker=MkQLtkNAfofyS6wruIyPfJ5g0Wr4-9B19Rds9nNL5-aLIP0Kipja4aOsXctaIHK_) ![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Michigan Avenue Chicago Downtown Chicago CA $821 per person Dec 22 - Dec 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.8/10 Excellent! (1,070 reviews) Hotel in great location, would stay again Reviewed on Oct 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-22/2025-12-26/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&HotelClass=40&dealMarker=zsdb7AqbqTyQd7e-XzjFSy_XhBeJyauzGRMjYhPak_H2KoXnxknm4PBfuiOGpVds) ![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 $496 per person Jan 17 - Jan 20 found 23 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (1,110 reviews) Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly. Reviewed on Oct 16, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=MkQLtkNAfofyS6wruIyPfDHB5UjQD-m5oFxcRPXuhm0XokjFFrwEnY3PJQr5JQNa) ![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 $791 per person Dec 12 - Dec 14 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,761 reviews) The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat. Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-14/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=zsdb7AqbqTyQd7e-XzjFS7YMZGfborOgqdHkiSzvo91ev8rce3gTyNk_-6iPqyND) ![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 $870 per person Dec 12 - Dec 14 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,006 reviews) This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend! Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-14/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=zsdb7AqbqTyQd7e-XzjFS7YMZGfborOgqdHkiSzvo91NYbZX8T3vARbtDqsiWPPD) 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/2025-11-22/2025-11-29/?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. ![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 $791 per person Dec 12 - Dec 14 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,761 reviews) The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat. Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-14/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=zsdb7AqbqTyQd7e-XzjFS7YMZGfborOgqdHkiSzvo91ev8rce3gTyNk_-6iPqyND) ![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 $870 per person Dec 12 - Dec 14 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,006 reviews) This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend! Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-14/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=zsdb7AqbqTyQd7e-XzjFS7YMZGfborOgqdHkiSzvo91NYbZX8T3vARbtDqsiWPPD) ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,024 per person Jan 17 - Jan 20 found 23 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (1,004 reviews) This is a very nice hotel. The staff is super accommodating. The location is one of the best in the area for shopping and dining. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&HotelClass=50&dealMarker=MkQLtkNAfofyS6wruIyPfADlxVIaEv7rqC_E7EWk9-RS6aHcuLLRuAHRsIbQIImy) 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/2025-11-22/2025-11-29/?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. ![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 $424 per person Jan 17 - Jan 20 found 23 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9/10 Wonderful! (1,011 reviews) Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&HotelClass=40&dealMarker=MkQLtkNAfofyS6wruIyPfJ5g0Wr4-9B19Rds9nNL5-aLIP0Kipja4aOsXctaIHK_) ![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 $496 per person Jan 17 - Jan 20 found 23 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (1,110 reviews) Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly. Reviewed on Oct 16, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=MkQLtkNAfofyS6wruIyPfDHB5UjQD-m5oFxcRPXuhm0XokjFFrwEnY3PJQr5JQNa) ![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 $758 per person Jan 17 - Jan 20 found 23 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (1,761 reviews) The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat. Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=MkQLtkNAfofyS6wruIyPfKc9Tml9E7UnE7R5ezJX-D3avzmGeWaIGuSQYyon4FmK) 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/2025-11-22/2025-11-29/?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 $747 per person Dec 29 - Jan 2 found 24 hours ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,110 reviews) Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly. Reviewed on Oct 16, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=o95OETKCA4o0Wln-FmQHTVK28CtTac770SmwiWg5pXn-9k-HV3rCS88gCgVcBIYV) ![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Michigan Avenue Chicago Downtown Chicago CA $821 per person Dec 22 - Dec 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.8/10 Excellent! (1,070 reviews) Hotel in great location, would stay again Reviewed on Oct 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-22/2025-12-26/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=zsdb7AqbqTyQd7e-XzjFSy_XhBeJyauzGRMjYhPak_H2KoXnxknm4PBfuiOGpVds) ![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 $835 per person Nov 26 - Nov 30 found 24 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Chicago (ORD) 9/10 Wonderful! (367 reviews) Friendly staff and great amenities Reviewed on Oct 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-26/2025-11-30/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=o95OETKCA4o0Wln-FmQHTU0qPbvgGyDGADuMn5yhsFLyP0SjfTLJ3IjiNMqRGVZ-) 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/2025-11-22/2025-11-29/?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 36. #### 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 $424. By booking your accommodations and flight together, you may be able to enjoy savings of up to 36. 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. 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