Southeast Wisconsin Ski Vacations

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Top Ski vacation packages in Southeast Wisconsin

Price found within the past 48 hours. Click for updated prices.
Lodge Geneva National

Lodge Geneva National

$421
per person
Nov 25 - Nov 28
just found
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.8/10 Excellent! (1,412 reviews)
The Craft de Italia Restaurant menu at Lodge Geneva National was very limited. I ordered the pork tenderloin with asparagus. The tenderloin was tasty but was too salty. The asparagus was inedible. It was unchewable. My wife said that it is just a decoration. Then why put it on a food plate. The price of the selection was high enough that it could have included a potato and/or a vegetable. I do not recommend this restaurant. The connected restaurants at nearby Geneva National are too inconvenient to go to, especially at night. The outside pool, bar and fire pit are excellent. The room also was very good.

Reviewed on Sep 19, 2026

Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

Save 100% on your flight
$766
per person
Oct 22 - Oct 25
found 13 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
8.8/10 Excellent! (1,006 reviews)
Just the food has less vegetarian options in the restaurant.

Reviewed on Sep 16, 2026

Destination Geneva National

Destination Geneva National

$566
per person
Oct 22 - Oct 25
found 13 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
9/10 Wonderful! (538 reviews)
The Staff went above and beyond. Had dinner Saturday night at the Hunt Club. Which was excellent. I woke up Sunday morning and realized that I left my credit card at the restaurant. The Hunt Club does not open until 4:00pm. The hotel staff found someone who had access to the Hunt Club and went and got my card. After I had breakfast at the golf course restaurant on was on my way home at 10:00am.

Reviewed on Sep 19, 2026

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3 Night Ski vacations in Southeast Wisconsin

Price found within the past 48 hours. Click for updated prices.
Lodge Geneva National

Lodge Geneva National

$421
per person
Nov 25 - Nov 28
just found
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.8/10 Excellent! (1,412 reviews)
The Craft de Italia Restaurant menu at Lodge Geneva National was very limited. I ordered the pork tenderloin with asparagus. The tenderloin was tasty but was too salty. The asparagus was inedible. It was unchewable. My wife said that it is just a decoration. Then why put it on a food plate. The price of the selection was high enough that it could have included a potato and/or a vegetable. I do not recommend this restaurant. The connected restaurants at nearby Geneva National are too inconvenient to go to, especially at night. The outside pool, bar and fire pit are excellent. The room also was very good.

Reviewed on Sep 19, 2026

Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

Save 100% on your flight
$766
per person
Oct 22 - Oct 25
found 13 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
8.8/10 Excellent! (1,006 reviews)
Just the food has less vegetarian options in the restaurant.

Reviewed on Sep 16, 2026

Destination Geneva National

Destination Geneva National

$566
per person
Oct 22 - Oct 25
found 13 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
9/10 Wonderful! (538 reviews)
The Staff went above and beyond. Had dinner Saturday night at the Hunt Club. Which was excellent. I woke up Sunday morning and realized that I left my credit card at the restaurant. The Hunt Club does not open until 4:00pm. The hotel staff found someone who had access to the Hunt Club and went and got my card. After I had breakfast at the golf course restaurant on was on my way home at 10:00am.

Reviewed on Sep 19, 2026

Don't see what you're looking for?
See all available trips from Columbus to Southeast Wisconsin
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4 Night Ski vacations in Southeast Wisconsin

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Hartford WI

Super 8 by Wyndham Hartford WI

$447
per person
Nov 5 - Nov 9
found 7 hours ago
Roundtrip non-stop flight included
Memphis (MEM) to Milwaukee (MKE)
6/10 (518 reviews)
Candlewood Suites Milwaukee Airport by IHG

Candlewood Suites Milwaukee Airport by IHG

$625
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Milwaukee (MKE)
8.6/10 Excellent! (487 reviews)
Crowne Plaza Milwaukee Airport by IHG

Crowne Plaza Milwaukee Airport by IHG

College Heights
$575
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Charleston (CHS) to Milwaukee (MKE)
7.8/10 Good! (1,098 reviews)
I use to go here at least once a year for an event and it has really gone downhill. As soon as you walk in the entrance smelled musty and damp. The free water was empty morning, noon, and night. I walked in my room the last night and saw a cockroach crawling on the night stand. I couldn’t sleep the rest of the night. The day I was leaving, the TV didn’t work. I called the front desk and they said maintenance would be right up. 30 minutes went by and I called again. The front desk said he’s coming right up. 30 mins later he said he had to stop at other rooms and is on his way. 25 more minutes goes by and he finally comes. He couldn’t fix it and said he would be right back and never came back. The only good thing was the food at the restaurant was served until 1am. I will never go back.

Reviewed on Sep 14, 2026

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Planning your Southeast Wisconsin ski vacation

What are some things I should consider when booking a Southeast Wisconsin ski trip package?

Yes, you want pristine powder and perfect runs, but take a moment to consider how close you want to be to the slopes, what extras you want from your resort, and—of course—how much après ski you intend to indulge in.

How can I find cheap Southeast Wisconsin ski packages?

Right now, ski trips start at just $421. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Southeast Wisconsin?

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Southeast Wisconsin. Book lessons so you can gear up to take on the rest of the mountain with confidence. Après awaits for all after an eventful day in the snow.

How much does a ski trip to Southeast Wisconsin cost?

Sensational ski trips to Southeast Wisconsin start from $421. Use the budget filter to find powder at your perfect price. As always, prices and availability are subject to change. Additional terms may apply.

When’s the best time of year to plan a ski trip to Southeast Wisconsin?

The best time to hit the slopes in Southeast Wisconsin depends on what you’re looking for. If you’re all about powder-packed pistes and brilliant blue-sky skiing conditions, aim for the middle of the season. Alternatively, if you’re willing to take a chance on start or end of season snow, you’ll bag much cheaper prices —just make sure there’s a spa or après bar to shelter in on white-out days.

Can I book Southeast Wisconsin ski packages with airfare?

Save money on your snow time by booking your accommodation, airfare, and car rental in a brilliant bundle. It’s both convenient and cash-flow friendly.

Can I book a Southeast Wisconsin ski trip with free cancellation and/or flexible dates?

Flexibility is always a bonus when you’re flying down the slopes—and it makes for an easier booking process, too. Check the payment option filter to find trips with free cancellation as well as buy now, pay later options.

Why should I book a ski package in Southeast Wisconsin with Expedia?

Simple search and fantastic filters make it easy to find, build, and book your dream Southeast Wisconsin ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.

Top Ski Southeast Wisconsin Hotels

Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

7036 Grand Geneva Wy Lake Geneva WI
  • 1 hour drive from American Family Field
Book a stay at this spa resort in Lake Geneva. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,000 reviews)
"Just the food has less vegetarian options in the restaurant."

Reviewed on Sep 16, 2026

Grand Geneva Resort & Spa
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way Lake Geneva WI
  • 1 hour drive from American Family Field
Book a stay at this spa aparthotel in Lake Geneva. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Timber Ridge Lodge and Waterpark
Holiday Inn Club Vacations at Lake Geneva Resort by IHG

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

7036 Grand Geneva Way Lake Geneva WI
  • 1 hour drive from American Family Field
Book a stay at this spa resort in Lake Geneva. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
Holiday Inn Club Vacations at Lake Geneva Resort by IHG
See all 2,479 properties in Southeast Wisconsin
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

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