Southern Wisconsin Ski 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 $4,200 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 Ski hotel deals in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
The Pfister Hotel

The Pfister Hotel

Downtown Milwaukee
CA $860
per person
Nov 20 - Nov 23
found 8 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Milwaukee (MKE)
9.6/10 Exceptional! (2,229 reviews)
The staff was wonderful and helpful. They were always available when you needed something extra.

Reviewed on Sep 1, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,436
per person
Oct 2 - Oct 6
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
Thanks for service

Reviewed on Sep 2, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,407
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,156
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

Downtown Milwaukee
CA $1,726
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Milwaukee (MKE)
9.8/10 Exceptional! (2,661 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Southern Wisconsin
View all trips

5* Ski holidays in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,407
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $2,173
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The staff was so kind and helpful. Great location and dining options. The room was spotless and comfortable

Reviewed on Aug 30, 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
CA $2,512
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.8/10 Exceptional! (1,013 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Southern Wisconsin
View all trips

3 Night Ski holidays in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,407
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,620
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
Thanks for service

Reviewed on Sep 2, 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
CA $1,633
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,339 reviews)
Love staying at the Emily! Everyone is always so friendly and helpful and the loft style rooms are super comfortable and spacious. The neighborhood has the best food and coffee of every type within walking distance and many clubs as well including Garcia's and Broken Hearts.

Reviewed on Aug 31, 2026

Don't see what you're looking for?
See all available trips from Columbus to Southern Wisconsin
View all trips

4 Night Ski holidays in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,436
per person
Oct 2 - Oct 6
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
Thanks for service

Reviewed on Sep 2, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,698
per person
Nov 4 - Nov 8
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Freehand Chicago

Freehand Chicago

Downtown Chicago
CA $2,050
per person
Oct 9 - Oct 13
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
7.8/10 Good! (3,328 reviews)
The room was very small and the lighting was very bad. I’ve stayed in other “affordable lifestyle” hotels before. In order for ‘small’ to work, it has to be very well thought out and designed. This king room was not. Two very dim light fixtures in the main room, neither of which illuminated the full length mirror area. Only one working outlet, far from the bed and nightstands. (There was a nonfunctional one slightly closer. Also the AC remote’s batteries were so drained you could barely see the LCD characters. I reported both to the front desk twice to no avail.) Nowhere to set the ironing board. Very dim lighting at the bathroom mirror. I could barely tell what I was doing as I was getting ready. It was just not a functional room. That said, the aesthetic is nice, and the lobby and common spaces were lovely. But I would have rather had a bland, functional room where I could see myself in the mirror and plug in my phone.

Reviewed on Sep 2, 2026

Don't see what you're looking for?
See all available trips from Columbus to Southern Wisconsin
View all trips

Plan the ultimate ski vacation in Southern Wisconsin

What are some benefits when booking ski vacations in Southern Wisconsin?

If you're interested in skiing, there's nothing quite like a ski vacation. These trips are designed to allow you to enjoy being on the slopes and relax in tranquil and convenient accommodations at the end of the day. Amenities on ski trips can be pretty upscale, so it's easy to relax in a hot tub or at a spa in between your skiing excursions. Plus, they can put you right next to the slopes. You'll even find a variety of different vacation types available whether you're looking for family friendly, cheap, or even last minute ski vacations.

How can I book the best ski vacation in Southern Wisconsin?

It is most important to implement the ski filter in your search when trying to find a ski vacation that will make you happy. Using the filter will automatically remove any entries that don't offer the skiing opportunities you want. After that, you'll need to think about what specifically you want from Southern Wisconsin, and think about the time of year that's best to visit.

How can I find cheap ski vacations?

Cheap ski vacations are readily available in Southern Wisconsin with some as cheap as CA $860. You can see the cheapest options by sorting your accommodation choices by price, which automatically puts the least-expensive results at the top of the list. You may also want to consider an accommodation with a kitchen, so you can cook instead of eating out.

Can I book ski packages?

Yes, ski packages are readily available throughout Southern Wisconsin. All you have to do is put in your travel dates and see what's available. When you book a ski package, you may be able to enjoy discounts with savings of up to 28 when you book your accommodation and your flight together.

What should I consider when booking family ski vacations?

The key to a successful family ski vacation is ensuring that your family is kept happy and entertained. Consider what your family members are interested in and the kind of vacation they want. If they have little skiing experience, for example, you may want to opt for an accommodation that offers ski lessons or a kid's club. Various slope difficulties may be essential in providing opportunities for everyone at Southern Wisconsin.

Can I book all-inclusive ski vacations in Southern Wisconsin?

Yes, all-inclusive ski trips are available and may be precisely what you're looking for. All you have to do is include the filter for all-inclusive stays, and your search results will only show the accommodations that provide this handy feature that allows you to plan your entire trip to Southern Wisconsin in advance.

What's the best time of year to plan a ski trip?

The apparent answer to when you should plan a ski trip is in winter, but other details are important too. If you book for Southern Wisconsin's high season around January and February, you'll likely find increased prices. It's generally best to opt for the early or late season in December and April, as prices tend not to be quite as high.

How can I find the best deals on ski packages in Southern Wisconsin?

When you're looking for cheap ski vacations, there are a few factors you can take advantage of to help get the best deals. Travelling during the off-season can be cheaper since there's more availability. However, the beginning and end of the season tend to be the most affordable for skiing.

Can I book a ski vacation that's fully refundable?

Being fully refundable is a feature you'll find on several accommodation packages in Southern Wisconsin. You can even search for it explicitly using a filter for full refundability.

Why should I book a ski vacation package with Expedia?

When you book with Expedia, you'll find everything you need for cheap ski vacations, luxury ski vacations and everything in between in one central location. You may even be able to enjoy discounts for booking your accommodation and your flight together with savings of up to 28. With Expedia Rewards, you can earn points towards your next booking.

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.