Title: All inclusive Vacations in Southwest Wisconsin 2026 | Expedia.ca ![](https://images.trvl-media.com/place/5957/f96cbf4a-3a46-4cf7-b7f2-0fff893f2f53.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southwest Wisconsin All inclusive Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Inbal Arieh - ## 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 Southwest Wisconsin Price found within the past 48 hours. Click for updated prices. ![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 $694 per person Apr 23 - Apr 26 found 22 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (766 reviews) room was great and staff were always great help Reviewed on Feb 14, 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 $866 per person Apr 23 - Apr 26 found 22 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Rooms were great and breakfast was delicious Reviewed on Feb 14, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $799 per person Apr 23 - Apr 26 found 22 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent. Reviewed on Feb 9, 2026 ![Stay One Chicago](https://images.trvl-media.com/lodging/113000000/112870000/112868000/112867973/0bd05cf3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Stay One Chicago Downtown Chicago CA $2,385 per person Apr 28 - May 4 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) No reviews The property was great, the room was awesome! The "Stay One Chicago" is really just a name on paper, and maybe one employee who is physically at the property. I am pretty sure that he wasn't even directly employed by the "hotel". So in a nutshell, the organization has not worked out any kind of structure for checking in other than the guy that told us to download the Door, OR the Latch app. He said that the app is very difficult to get logged into. Long story made short, we wasted the 1st 2 hours in the hotel trying to get the app (both my wife and I). The app never worked, and we finally got physical key cards from the guy working for the building. There was one small piece of paper with scan codes for restaurants, but zero property maps, rules, room cleaning, and nothing explaining how to get to, or use any of the amenities. It was the worst 1st 3 hours of a vacation that we have experienced. I still gave it a 4-star because the local people were so nice and helpful, even though helping us wasn't part of their job. The valet guys were the best, super nice, and helpful. Reviewed on Feb 10, 2026 ![Hyatt Regency Deerfield](https://images.trvl-media.com/lodging/1000000/30000/21800/21767/26a8e15a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Deerfield CA $832 per person Apr 24 - Apr 30 found 5 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 8.6/10 Excellent! (1,007 reviews) nice large room with updated decor, gorgeous bath with super White, clean, fresh towels and linens on the bed! Reviewed on Feb 1, 2026 Don't see what you're looking for? See all available trips from Columbus to Southwest Wisconsin [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-15/2026-03-22/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=RFD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* All inclusive holidays in Southwest Wisconsin Price found within the past 48 hours. Click for updated prices. ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago CA $1,104 per person Mar 23 - Mar 26 found 13 hours ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Best service in Chicago — whether desk service, room service, etc. Stunning property. Amazing bathtubs. Reviewed on Feb 12, 2026 ![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 $2,509 per person Apr 28 - May 4 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.6/10 Exceptional! (1,000 reviews) Everything was great… but the staff was absolutely amazing! Thank you for taking such great care of us. Reviewed on Jan 24, 2026 ![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 $1,452 per person Apr 3 - Apr 6 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better. Reviewed on Jan 26, 2026 Don't see what you're looking for? See all available trips from Columbus to Southwest Wisconsin [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-15/2026-03-22/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=RFD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night All inclusive holidays in Southwest Wisconsin Price found within the past 48 hours. Click for updated prices. ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $799 per person Apr 23 - Apr 26 found 22 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent. Reviewed on Feb 9, 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 $866 per person Apr 23 - Apr 26 found 22 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Rooms were great and breakfast was delicious Reviewed on Feb 14, 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 $1,193 per person Mar 19 - Mar 22 found 4 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Lovely room. Excellent staff. Reviewed on Feb 3, 2026 Don't see what you're looking for? See all available trips from Columbus to Southwest Wisconsin [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-15/2026-03-22/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=RFD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night All inclusive holidays in Southwest Wisconsin Price found within the past 48 hours. Click for updated prices. ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $747 per person Apr 2 - Apr 6 found 14 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent. Reviewed on Feb 9, 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 $1,124 per person Apr 29 - May 3 found 1 day ago Roundtrip flight included Toronto (YTZ) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Rooms were great and breakfast was delicious Reviewed on Feb 14, 2026 ![Staypineapple, An Iconic Hotel, The Loop](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/eac2e31f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Staypineapple, An Iconic Hotel, The Loop Downtown Chicago CA $876 per person Apr 29 - May 3 found 1 day ago Roundtrip flight included Toronto (YTZ) to Chicago (ORD) 9.4/10 Exceptional! (1,003 reviews) Staff was great. The hotel is quirky and cool with an unbeatable location right in the middle of shopping, theater and restaurants. Easily walkable to the Art Institute and Millennium Park. The rooms are not large, and could use some new furniture, but very clean. Will definitely be back. Reviewed on Feb 14, 2026 Don't see what you're looking for? See all available trips from Columbus to Southwest Wisconsin [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-15/2026-03-22/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=RFD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Embark on an unforgettable all-inclusive trip to Southwest Wisconsin including airfare with Expedia #### What are some benefits of booking an all-inclusive vacation? When you opt for an all-inclusive vacation to Southwest 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 Southwest 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 22\. #### Why should I book Southwest Wisconsin vacations that are all inclusive and adults only? Adults-only stays in Southwest 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 Southwest 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 Southwest Wisconsin? If you're looking to save, you'll find a wide range of prices available, ranging from CA $694\. By booking your accommodations and flight together, you may be able to enjoy savings of up to 22\. 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 Southwest Wisconsin? If you've implemented the 5-star filter when searching for your all-inclusive vacation in Southwest 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 Southwest Wisconsin vacation packages that are all inclusive for the family? The most important thing to consider for all-inclusive family vacations to Southwest 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 Southwest Wisconsin's nightlife. #### How can I find the best deals on all-inclusive vacations in Southwest 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. ## All inclusive Hotels in Southwest Wisconsin ![AmericInn by Wyndham Wisconsin Dells](https://images.trvl-media.com/lodging/1000000/970000/970000/969964/5e05acd0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### AmericInn by Wyndham Wisconsin Dells 550 State Hwy 13 Wisconsin Dells WI - 2 hours drive from University of Wisconsin-Madison Book a stay at this family-friendly hotel in Wisconsin Dells. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ... 8.2/10 Very Good! (1,010 reviews) Nise staff and room Reviewed on Feb 8, 2026 [](https://expedia.ca/Wisconsin-Dells-Hotels-AmericInn-By-Wyndham-Wisconsin-Dells.h969964.Hotel-Information) ![AmericInn by Wyndham Madison WI](https://images.trvl-media.com/lodging/1000000/990000/981000/980986/31982ce2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### AmericInn by Wyndham Madison WI 1754 Thierer Rd Madison WI - 15 min drive from University of Wisconsin-Madison Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ... 6.6/10 (262 reviews) Loved the breakfast, loved the nice view of the snow outside very clean 10/10 worth the stay☺️ Reviewed on Feb 13, 2026 [](https://expedia.ca/Madison-Hotels-AmericInn-By-Wyndham-Madison-WI.h980986.Hotel-Information) ![AmericInn by Wyndham Black River Falls I-94 on ATV Trail](https://images.trvl-media.com/lodging/1000000/860000/856300/856209/845a315a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### AmericInn by Wyndham Black River Falls I-94 on ATV Trail I-94 at Exit 116/Hwy. 54 East Black River Falls WI - 5 hours drive from University of Wisconsin-Madison Book a stay at this business-friendly hotel in Black River Falls. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our ... 7/10 Good! (598 reviews) Staff was great but we didn’t get the suite we reserved and they only had two tv channels working. Reviewed on Nov 13, 2025 [](https://expedia.ca/Black-River-Falls-Hotels-AmericInn-By-Wyndham-Black-River-Falls-I-94-On-ATV-Trail.h856209.Hotel-Information) [See all 3,708 properties in Southwest Wisconsin](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6059824) 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.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 the Dominican Republic ](https://www.expedia.ca/lp/theme-vacations/all-inclusive-vacations/50/Dominican-Republic) ## More Vacations Ideas [Flights to Southwest Wisconsin ](https://expedia.ca/Cheap-Flights-To-Southwest-Wisconsin.d6059824.Travel-Guide-Flights)[ Southwest Wisconsin Hotels ](https://expedia.ca/Southwest-Wisconsin-Hotels.d6059824.Travel-Guide-Hotels)[ Southwest Wisconsin Vacation Rentals ](https://expedia.ca/Southwest-Wisconsin-Vacation-Rentals.d6059824.Travel-Guide-VacationRentals)[ Southwest Wisconsin Car Rentals ](https://expedia.ca/Car-Rentals-In-Southwest-Wisconsin.d6059824.Car-Rental-Guide)[ Southwest Wisconsin Vacations ](https://expedia.ca/Southwest-Wisconsin.d6059824.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. Scan the QR code with your device camera and download our app