Southern Wisconsin Golf Vacations

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Flight and Golf hotel deals in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $847
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Nice property overall Room was very nice Location excellent

Reviewed on Oct 19, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
CA $1,026
per person
Nov 25 - Nov 30
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,754
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
CA $1,815
per person
Dec 29 - Jan 1
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Victoria Resort and Bed & Breakfast

Victoria Resort and Bed & Breakfast

North Side
CA $1,785
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (154 reviews)
This is a lovely place to stay with great amenities and special touches. The breakfast was amazing! Highly recommend this gem just 2 blocks from the beach and easy bike ride to downtown. The owner is onsite and very friendly.

Reviewed on Oct 10, 2026

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5* Golf holidays in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
CA $1,614
per person
Dec 29 - Jan 1
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,003 reviews)
The service was truly outstanding. Every member of the staff was welcoming, professional, attentive, and genuinely committed to making our stay memorable. Our room was absolutely beautiful—spacious, impeccably maintained, elegantly designed, and extremely comfortable. The quality of the accommodations exceeded our expectations. The food was equally impressive, with delicious dishes, excellent presentation, and wonderful service. Every dining experience was a pleasure. What really sets this hotel apart is the combination of its beautiful property, exceptional hospitality, and the attention given to every little detail. It’s the kind of place that makes you feel genuinely appreciated as a guest.

Reviewed on Oct 19, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,754
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
CA $1,815
per person
Dec 29 - Jan 1
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
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3 Night Golf holidays in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $847
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Nice property overall Room was very nice Location excellent

Reviewed on Oct 19, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,754
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
CA $1,815
per person
Dec 29 - Jan 1
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Southern Wisconsin
View all trips

4 Night Golf holidays in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Downtown Chicago
CA $1,023
per person
Nov 25 - Nov 29
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.6/10 Excellent! (1,841 reviews)
I didn’t like the fact that they said I would get a discount on being a senior citizen. The party lied and price was more

Reviewed on Oct 20, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,833
per person
Nov 21 - Nov 25
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,046
per person
Dec 28 - Jan 1
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
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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 $847, 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 25, 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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.