Title: Golf Vacations in Southern Wisconsin 2026 | Expedia.ca ![](https://images.trvl-media.com/place/2325/f29f5e3d-0eb0-45b8-94f1-06284f8af3d0.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southern Wisconsin Golf Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Evae - ## 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 Golf hotel deals in Southern Wisconsin 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 $666 per person Apr 8 - Apr 11 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Very nice and staff was amazing! Reviewed on Jan 25, 2026 ![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Orrington / Evanston Downtown Evanston CA $753 per person Apr 13 - Apr 17 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 7.6/10 Good! (1,002 reviews) Courteous staff, good breakfast selection, Reviewed on Jan 23, 2026 ![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 $774 per person Apr 8 - Apr 11 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Clean room and amenities Reviewed on Jan 8, 2026 ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/7e178380_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Downtown Chicago CA $882 per person Feb 24 - Feb 28 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 8.6/10 Excellent! (2,008 reviews) The room was clean. The staff was very nice. They even held on to our stuff on our last day after check out so we could explore the town luggage free! Reviewed on Jan 23, 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 $920 per person Mar 13 - Mar 16 found 24 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Property was clean, welcoming, pet friendly Reviewed on Jan 18, 2026 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/2026-02-25/2026-03-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Golf 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 $874 per person Mar 13 - Mar 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The room was boring thought it would be cleaner updated for the price best part was the view 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 $1,328 per person Apr 8 - Apr 11 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) First time there. Staff was helpful and they provided excellent memorable service Reviewed on Jan 20, 2026 ![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 $1,107 per person Mar 8 - Mar 11 found 20 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Staff was wonderful. Reviewed on Jan 25, 2026 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/2026-02-25/2026-03-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Golf holidays in Southern Wisconsin 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 $666 per person Apr 8 - Apr 11 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Very nice and staff was amazing! Reviewed on Jan 25, 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 $1,136 per person Mar 8 - Mar 11 found 20 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) First time there. Staff was helpful and they provided excellent memorable service Reviewed on Jan 20, 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 $732 per person Apr 22 - Apr 25 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Property was clean, welcoming, pet friendly Reviewed on Jan 18, 2026 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/2026-02-25/2026-03-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Golf holidays in Southern Wisconsin 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 $698 per person Apr 13 - Apr 17 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Very nice and staff was amazing! Reviewed on Jan 25, 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 $1,270 per person Mar 7 - Mar 11 found 20 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The room was boring thought it would be cleaner updated for the price best part was the view Reviewed on Jan 24, 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 $851 per person Apr 13 - Apr 17 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Property was clean, welcoming, pet friendly Reviewed on Jan 18, 2026 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/2026-02-25/2026-03-04/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Discover the ultimate golf vacation from Southern Wisconsin with Expedia #### What are some benefits when booking golf vacations from Southern Wisconsin? Booking a golf vacation means putting golf at the centre of your entire experience. Not only will you be able to enjoy easy access to the greens, but you'll often have access to all the equipment you need as well. Plus, golf stays tend to be on the more luxurious end of the spectrum, so you're likely to have some other high-end amenities as well. #### How can I find the best golf vacations in Southern Wisconsin? The best way to find golf vacations in Southern Wisconsin is to take advantage of numerous search filters. You can look for golf stays specifically, with additional filters available for certain courses in some destinations. Plus, if you travel during the off-season in , you may even be able to get high-end stays at a discount. #### Are there cheap golf packages available? Yes, you'll find prices as low as CA $666, but the overall price depends on several factors. The time of year you travel to Southern Wisconsin and the amenities you opt for can play a role in the cost of your package. Some package deals offer discounts of up to 31, but that's just a general trend rather than a guarantee. #### Can I book golf and spa vacation packages? Golf is often considered a luxury activity, so it's only natural that it be paired with other high-end experiences. You can implement the spa filter to sort for properties that have spa facilities, which can be especially useful for resting and rejuvenating in between games. #### How can I find luxury golf vacations in Southern Wisconsin? A lot of golf vacations are already luxurious given the nature of the game, but there are a few things you can do to push it as far as it can go. Use search filters to highlight only 5-star properties to ensure you're getting the best of the best. Business-class flights are available as well in most cases. #### Can I book an all-inclusive golf vacation in Southern Wisconsin? In many cases, yes. There's even a search filter for all-inclusivity, so you can sort for all-inclusive stays specifically. Even when an all-inclusive experience that matches your needs isn't available, you may be able to find some half-board options. This is also one of the best ways to find luxury golf vacations. #### Why should I book golf packages including flights? When you book your flight and your accommodations together, you can enjoy some serious savings compared to what you'd find booking separately. We're your one-stop shop for all your travel needs, and convenience is just the beginning when booking golf vacations from Southern Wisconsin with us. #### Should I book a last-minute golf vacation? Booking last-minute to Southern Wisconsin shouldn't be your first choice, but if you like to travel spontaneously, there are a few benefits to enjoy. Occasionally, you may be able to save money by booking last-minute, as accommodations are interested in filling their last few vacancies as fast as they can. The deals aren't guaranteed, however, so keep that in mind when planning. Sometimes, accommodations will simply be sold out. #### Can I book a golf vacation that is fully refundable? Yes, you'll find several options that are fully refundable among our packages in Southern Wisconsin. You can even filter for fully refundable stays specifically. Just remember to check out each accommodation's policy specifically to make sure your booking qualifies. #### Why should I book my golf trip with Expedia? When you book with Expedia, you can enjoy a one-stop shop for all your travel needs. You can search through a massive collection of packages and potentially unlock discounts by booking your flight and accommodations together. Even more discounts may be available for Expedia Rewards members, such as special deals and the ability to earn points to put toward discounts on future bookings. ## 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 Golf Vacation Destinations > - [Golf vacations in Mexico ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/117/Mexico) > - [Golf vacations Myrtle Beach ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/601685/Myrtle-Beach) > - [Golf vacations in Portugal ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/147/Portugal) > - [Golf vacations in Thailand ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/178/Thailand) > - [Golf vacations in Belek ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/6034717/Belek) > - [Golf vacations in Las Vegas ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/178276/Las-Vegas) > - [Golf vacations in Scotland ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/11219/Scotland) > - [Golf vacations in Tenerife ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/6047194/Tenerife) > - [Golf vacations in the Caribbean ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/6022969/Caribbean) > - [Golf vacations in Lanzarote ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/282/Lanzarote) > - [Golf vacations in Italy ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/86/Italy) > - [Golf vacations in Turkey ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/183/Turkey) > - [Golf vacations in Vilamoura ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/11395/Vilamoura) > - [Golf vacations in Ireland ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/84/Ireland) > - [Golf vacations in the Dominican Republic ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/50/Dominican-Republic) > - [Golf vacations in the United Kingdom ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/190/United-Kingdom) > - [Golf vacations in Hawaii ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/213/Hawaii) > - [Golf vacations in Algarve ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/182215/Algarve) > - [Golf vacations in Cyprus ](https://www.expedia.ca/lp/theme-vacations/golf-vacations/45/Cyprus) ## 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. Scan the QR code with your device camera and download our app