Resort info on ski vacation packages

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Windy City Ski and Snowboard offers ski vacation packages on several different Midwest ski resorts. We can offer packages to Cascade Mountain, Chestnut Mountain, Devil’s Head Resort and Granite Peak. You can find out which one of these ski areas is best for your level and recreational needs on our website. You can see details… read more

Ski vacation packages available as gift cards

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After one of the hottest summers on record, a ski vacation is the very thing we all need. If you have a friend or family member that is hankering after the slopes, a gift card for Windy City Ski & Snowboard could hit the spot. Maybe you know somebody who recently moved from the ski… read more

Bus Trips Might Be the “Key To Winter Happiness”

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We know our bus trips to the Midwest’s best ski resorts are fantastic! But maybe you need more convincing. Head over to our testimonials page to see what others have to say about our bus and ski trips, and how Windy City Ski holds the key to winter happiness! And if you want to read… read more

Which Ski Trips Are Right For You?

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Have you started to dream about your 2012-2013 ski trips? Now is the time to start thinking about which trip is right for you! Windy City Ski offered a variety of ski trips. If you just want to hit the slopes for a day, our buses will drive you up in the morning and take… read more

Calendar for 2012-2013 Ski Vacation Packages Coming Soon!

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Summer is slowly rolling out, making way for cooler temperatures and hopefully snow! Many are predicting an early fall this year, and we’re hoping for an early winter, as well. We can’t wait for the snow to start falling so we can get back out on the slopes. We’re betting you can’t wait, either! The… read more

Ski Vacation Packages Bring the Best Slopes to You

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When you live in the city, going on vacation can almost seem like a chore. And with our fast-paced, Chicago lives, few people need vacations like we do. Unfortunately, going on vacation can sometimes seem like it generates more stress than it alleviates. There are concerns with bookings, planning, and most of all travel. Thankfully,… read more

Ski Bus Trips Make Travel Easy

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Winter brings many things: the promise of fresh powder, the fun and excitement of a perfect ski or snowboard run on your favorite slope, and unfortunately, less-than-stellar driving conditions. We all know how poor driving conditions can turn an otherwise lovely trip into a nightmare of stress and anxiety. As unfortunate as snowy roads may… read more

Planning Ski Trips to Escape the Summer Heat

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There has been a recent upswing in the amount of Chicago locals planning ski trips. Though we’re still several months from prime ski season, folks in the Midwest have been planning ahead in an attempt to free their minds from the oppressive summer heat waves. Purchasing ski trip packages in advance can allow for increased… read more

Windy City Ski’s Last Ski Bus Trip

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Join Windy City Ski on our last ski trip of the season to Devils Head on March 24.  Ride with us on our luxury bus -relax eat, drink and watch a movie!!! Then ski or snowboard and enjoy a fun and relaxing ride home.  We would like to thank all our passengers this season who… read more

Chestnut Mountain, Ski, Snowboard Trip & Transportation

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Plan on going riding with Windy City Ski to Chestnut Mountain on March 17. Chestnut is the Midwest snowboarding haven for boarders and skiers alike, Chestnut Mountain Resort’s terrain park, the Farside, is the largest of its kind in the Midwest. The Farside has more than 25 rails and features and is served by its… read more

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