Four Fabulous Family-Friendly Resorts in Wisconsin and Illinois for Winter Getaways

Dec 16, 2024

Winter is finally here, and we’re ready to kick back, relax, and immerse ourselves in the season with our favourite people. What better way to enjoy your holiday breaks and winter vacations than taking a trip to the finest Ski and Snowboarding Resorts in the Midwest! Whether you’re a beginner or a seasoned pro, looking for something exhilarating or some good ol’ fashioned family friendly fun, these four fantastic winter destinations in Illinois and Wisconsin are sure to capture your attention. Check it out!

Four Fabulous Family-Friendly Resorts in Wisconsin and Illinois for Winter Fun

Chestnut Mountain Resort in Galena, Illinois

If you’re looking for family-friendly fun, this 220 acre park is a stellar option! Skiers and winter sports enthusiasts of all skill levels are welcome here. There are lots of opportunities to enjoy professional instruction to learn the basics in skiing or snowboarding, so you won’t miss out on a thing. There are 19 different ski-slopes to choose from, which means plenty of excitement and adrenaline for the seasoned skiing enthusiast. Elite snowboarders will rejoice to see the Farside Terrain Park offers more than 25 rails and different snow features to test your skills and tricks. Don’t have your own gear? No problem! There is an available rental shop as well as the fantastic Mountainside Outfitters, host to all the hottest gear and brands. Feeling hungry? Stop by the wonderful restaurant called The Summit for Breakfast, Lunch, and Dinner for a diverse menu with locally sourced options.

Ski Snowstar Winter Sports Park in Andalusia, Illinois

There’s more family fun to be had in Illinois with a 28-acre terrain park, 15 ski lanes, and 11 snowtubing hills! You can select group or individual lessons and can opt in for a package that includes equipment rentals as well; if you’ve got time to spare, there are also some fantastic Bunny & Kids camps to learn “boot camp” style, with a max of 30 students per class. There are also four very affordable eateries on site, allowing you to refuel between excursions so you can recharge: The Lodge, Peak’s Tavern, Fireside Lounge, Snack Shack. The ski slopes offer 15 trails across 28 acres and a 790 foot summit for exhilarating downhill skiing and snowboarding. The snowboarding terrain offers numerous opportunities to test your abilities with tubes, wall rides, jumps and more!

Cascade Mountain in Portage, Wisconsin

This family owned and operated park (since 1977!) sprawls across 175 acres! There’s a 900 foot long snow-tubing shoot, plus 48 trails for skiing and snowboarding. While this mountain does offer lessons, the slopes are best suited to the intermediate to advanced snowsports enthusiast, as many of the trails are quite challenging to navigate. For youth skiers with some experience, the mountain offers a Junior Racing program available to ages 6 through 18 where they can level up their skills. However, beginners and the snowsports averse will rejoice to find they won’t get left behind in the powder – The brand new Polar Park area offers opportunities for sledding, snow angels, snowball fights, and other winter fun (and it’s the only area of the park where sledding is allowed!) You can even rent a ski-in/ski-out cabin for the day that comfortably seats and heats up to 8 people for a break with your very own firepit and personal storage, perfect for lunch breaks with pals.

Granite Peak in Wausau, Wisconsin

This park is situated at the second-highest point in the state of Wisconsin, and has been a winter family favorite since the 1930s! The park covers more than 200 acres and offers 2 terrain parks, 1 learning park, 7 lifts, and infinite opportunities for fun in the snow. Choose from one of the 68 trails available to all different skill levels and find the perfect winter sports experience tailored just for you. And you simply must try the absolutely impressive 10,000 square foot Sundance Chalet, a restaurant offering Live Music, an outdoor deck, two immense fireplaces, 16 Midwest craft beer options, specialty signature cocktails, and 6 fire pits. Stop by the bar for a cocktail and appetizer, explore full menu service at Apres Ski, or grab a pizza and some pretzels at The Patio Pizza Shack. If that’s not enough excitement, you can swing on to the downtown area of Wausau and explore farm to table restaurants, local cafes, craft breweries, local shopping, and more.

Other wonderful winter sports resorts of note in the Midwest: