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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.
  • Sep 9 - Sep 13

    Marriott Milwaukee West + Flight

    Waukesha
    4 nights
    3.5 star property
    9.2/10 - Wonderful (1,002 reviews)
    Roundtrip Dallas (DFW) - Milwaukee (MKE)
    DFW - MKENonstop MKE - DFW1 stop
    $601
    $521
    per traveler
    found 1 day ago
    Marriott Milwaukee West
  • Sep 9 - Sep 13

    The Iron Horse Hotel + Flight

    Fifth Ward
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,262 reviews)
    Roundtrip Dallas (DFW) - Milwaukee (MKE)
    DFW - MKENonstop MKE - DFW1 stop
    $959
    $709
    per traveler
    found 1 day ago
    The Iron Horse Hotel
  • Sep 11 - Sep 13

    Comfort Suites Lake Geneva East + Flight

    Lake Geneva
    2 nights
    2.5 star property
    8.4/10 - Very Good (1,008 reviews)
    Roundtrip New York (NYC) - Chicago (ORD)
    LGA - MDWNonstop MDW - LGANonstop
    $603
    $564
    per traveler
    found 1 day ago
    Comfort Suites Lake Geneva East
  • Sep 3 - Sep 6

    Embassy Suites by Hilton Milwaukee Brookfield + Flight

    Brookfield
    3 nights
    3.5 star property
    9.0/10 - Wonderful (1,326 reviews)
    "Staff was very friendly. We enjoyed our stay."
    Reviewed August 2, 2026
    Roundtrip Dallas (DFW) - Milwaukee (MKE)
    DFW - MKENonstop MKE - DFWNonstop
    $570
    $543
    per traveler
    found 16 hours ago
    Embassy Suites by Hilton Milwaukee Brookfield
  • Sep 11 - Sep 14

    avid hotel Milwaukee West Waukesha by IHG + Flight

    Pewaukee
    3 nights
    2.5 star property
    9.4/10 - Exceptional (746 reviews)
    Roundtrip Los Angeles (LAX) - Milwaukee (MKE)
    LAX - MKE1 stop MKE - LAX1 stop
    $616
    $588
    per traveler
    found 1 day ago
    avid hotel Milwaukee West Waukesha by IHG

Discover the most popular places to visit in Southeast Wisconsin

Top Ski Southeast Wisconsin Hotels

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.

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 $521. 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 $521. 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.