Awesome Winter Wonderland Getaways in Wisconsin, Indiana, and Illinois for Holiday Break Vacations!

Welcome to Winter!  We can’t wait to spend our holiday break with friends and loved ones and exploring all of the adventures the season has to offer. There’s nothing as exhilarating as the crunch of fresh powder underfoot, and the brisk fresh air of the ski slopes or snowy trails. And, as always, please feel free to let us know your picks for winter getaways!  Your suggestions may make it into a future blog post!

 Whether you’re into the adrenaline rush of downhill skiing or snowboarding, wilderness trail hikes with snowshoes or cross-country skiing, or just a good ol’ fashioned sledding hill, we think you’re going to love the ideas we’ve got on our Winter Break Vacation destinations list.

Local Preserves & Trails for Snowshoeing, Sledding, Cross Country Skiing in Illinois and Wisconsin

• Lyons Woods Forest Preserve in Waukegan, IL
• Captain Daniels Wright Woods in Mettawa IL
• Adler Park in Libertyville, IL
• INdependence Grove Forest Preserve in Libertyville, IL
• Old School Forest Preserve in Libertyville, IL
• Lakewood Winter Sports Area in Wauconda, IL
• Moraine Hills State Park in McHenry, IL
• Illinois Beach State Park in Zion, IL
• Fort Sheridan Forest Preserve in Lake Forest, IL
• Captain DAniel Wright Woods Forest Preserve in Mettawa, IL
• Prairieview Education Center in Crystal Lake, IL
• Edward L Ryerson Conservation Area in Deerfield, IL
• Chiwaukee Prairie in Pleasant Prairie, WI
• Kenosha Silver Lake County Park in Salem, WI
• Richard Bong State Recreation Area in Kansasville, WI
• Parkside Cross-Country Ski Trail System in Kenosha, WI

The daredevils among us will love these destinations geared up for downhill skiing, snowboarding, and snowtubing!  These resorts are also one-stop-shopping on entertainment, dining, and plenty of other outdoor adventure fun beyond the expected. Check out our picks for best Ski and Snowsports Areas & Resorts worth the road trip!

Best Downhill Skiing and Winter Sports Destinations in Wisconsin, Indiana, and Illinois!

• Wilmot Mountain Ski Resort in Wilmot, WI
• Alpine Valley Resort in Elkhorn, WI
• Little Switzerland in Slinger, WI
• Fox Hill Ski Area in West Bend, WI
• The Mountain Top Ski and Adventure Center at Grand Geneva in Lake Geneva, WI
• Sunburst Ski Area in Kewaskum, WI
• Nutt Hill in Plymouth, WI
• Sundown Mountain Resort in Dubuque, IA
• Pines Family Ski Area in Valparaiso, IN
• Four Lakes Alpine Snowsports in Lisle, IL
• Snowstar in Andalusia, IL
• Norge Ski Club in Fox River Grove, IL
• Villa Olivia in Bartlett, IL
• Chestnut Mountain Resort in Galena, IL
• Gander Mountain in Antioch, IL
• Sagawau Environmental Learning Center in Lemont, IL

Looking to spend the break with quiet respite instead of being constantly on the move?  You’ll find all the rest and repose you’re craving on our Midwest Winter Getaways list.  We’ve found everything from charming cottages to log cabin retreats, so no matter your flavor or passion, you’ll have a blissful stay.

Peaceful Wintry Weekend Getaways in Wisconsin and Illinois

• Dragonfly Bed and Breakfast in Antioch
• Christmas House Bed and Breakfast in Racine, WI
• Manor on the Mile in Franksville, WI
• Lilac Cottage in Bowen Park
• Augustus Chetlain Home and Log Cabin Guest Houses in Galena
• Lombard Log Cabin in Four Seasons Park
• Kishauwau Cabins in Tonica
• Goldmoor Inn in Galena
• Copperstone Inn at Orchard Ridge Farms
• Starved Rock Cabins in Oglesby
• White Pines Inn at Mount Morris
• Grizzly Jack’s Grand Bear Resort
• Galena Cellars in Galena
• Chicago Athletic Association Hotel in Chicago
• Heartland Lodge in Nebo
• Big Sky Cabins in Alto Pass
• Nauvoo Log Cabins in Nauvoo
• Haagen Haus in Alton
• Timber Ridge Outpost in Karbers Ridge
• Pere Marquette Lodge in Grafton
• Peace of Earth Lodge in Rushville

If you prefer the staycation route, there’s also lots of fun things to do right here in Waukegan!  Check out our many local restaurants, cafes, and small businesses.  And let us know if you have a recommendation for a nearby activity, recommended accommodations for cozy winter getaways, and we may just feature it in an upcoming post!

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