The Best Midwest Winter Getaways

Coastal lifestyle magazines often get the Midwest wrong. There’s almost always a portrait of farmers and hectares upon hectares of corn fields and images of a frozen Chicago. And sure, the sweet yellow crop may be Iowa’s single largest export, and yes, Chicago can and does get incredibly cold in the winter, but throughout the Great Lakes region, there is history to explore and an infinite number of outdoor recreation opportunities.

It’s a theme that Chicago-area residents are well versed in — adventure awaits in any direction you decide to drive.

And just like the thousands of towns scattered throughout the region, there is something for everyone. Those looking for a thrill will find miles upon miles of groomed cross-country skiing paths in Door County, Wisconsin. But say you just want some much-needed rest and relaxation — you can get that too. Here are just a few of our favorite sites for adventure, small town charm, and relaxation within a few hours’ drive from downtown Chicago.

Photo by Wilmot Mountain

Sites for the adventure-seekers:

Looking for some outdoor fun and exploration in serene environs? Pack your hard-shell coat and gloves and head north towards Sturgeon Bay in Door Country, Wisconsin for some of the best cross-country skiing within reach of the Chicago area. Some of the best locations include the 48-mile-long Ahnapee State Trail, which stretches from Sturgeon Bay to Kewaunee, and the Crossroads at Big Creek and Door County Land Trust nature preserves.

If downhill skiing is more your speed, consider a trip to Wilmot Mountain Resort in Wilmot, Wisconsin. It may not be Vail, but with 23 trails and seven lifts spanning 120 acres, Wilmot Mountain is the closest thing a Midwesterner gets to the true spirit of Alpine skiing and snowboarding. They even have snow tubing, which is a blast for all ages. And then there’s the recently remodeled base lodge, perfect for warming up before the next lift.

Winter hiking may sound like an oxymoron, but in reality, steady cardio activity combined with cooler temps can make for a quite comfortable experience. That, and you can expect to see far fewer crowds at popular attractions such as Starved Rock State Park in Utica, Illinois. Filled with unique geological features such as miniature canyons and waterfalls, this outdoor attraction is a staple for those living in and around the Chicago area. Bring your camera to capture breathtaking images of frozen waterfalls.

Photo from

Escape to cozy small-town charm:

The Midwest is full of picturesque small towns with historic main streets that appear as though they’ve been trapped in amber over the last 100 years. One of these historic towns is Galena, Illinois, located about a three-hours’ drive from downtown Chicago. The main drag feels almost like a European-style mountain town with rows of Victorian-era buildings brushing shoulders down a gently winding road. And a light dusting of snow adds even more charm to this already enchanting place.

Lovers of classic Americana will appreciate Three Oaks, Michigan. With less than 2,000 residents, this village is truly a small town by definition, but there’s plenty to see and do. The quaint downtown boasts numerous independent shops and cozy restaurants. And then there’s the Journeyman Distillery where spirits such as gin and whiskey are produced and poured for tourists’ enjoyment.

Small towns in Wisconsin have a specific kind of charm. Towns like Cedarburg have a distinct European flavor with sturdy, stone-clad buildings and gristmills. And fortunately for today’s visitors, much of the historic center of Cedarburg remains in-tact and thriving. Take a step back in time and explore this town’s collection of over 200 buildings listed on the National Register of Historic Places.

Photo from Grand Geneva

Places ripe for rest and relaxation:

Maybe you’re just looking to get away from the city and have a weekend of quiet relaxation. One of the more premier resort destinations within reach of the Chicago area is the American Club in Kohler, Wisconsin. The grand century-old Tudor-style manor which houses the resort harkens to the wealth and glamour of The Great Gatsby era — and rightfully so. Guests can expect to be pampered at the hotel’s spa and enjoy gourmet room service.

Even closer to the Chicago area is the Grand Geneva Resort in Lake Geneva, Wisconsin. You can either choose your own adventure or let the resort do all of the planning by choosing one of its many different package deals. There’s also special holiday and winter-specific programming and events.

Written by AJ LaTrace
AJ LaTrace is a freelance writer, editor, and photographer covering Chicago real estate, architecture, and neighborhoods. His work has been featured in Chicago magazine, Time Out Chicago, Michigan Avenue Magazine, Curbed Chicago, Block Club Chicago, and others.