Get us in your inbox

Devil's Lake State Park
Photograph: Shutterstock

The most secluded getaways from Chicago

Escape Chicago at these cozy secluded getaways located throughout the Midwest.

Emma Krupp
Written by
Sarah Medina
Emma Krupp

Living in the city is great, but it's natural to want to journey to a place that's a bit more secluded from time to time. If your budget precludes you from jetsetting around the world, that doesn't mean you have to stay hunkered down. Instead of pining for a lakeside cottage, might we suggest a Midwestern weekend getaway from Chicago? We rounded up a list of the most incredible remote destinations throughout the region, perfect for holing up for a few days. Go hiking along Lake Michigan or book an extra cozy Airbnb cabin near Chicago in Wisconsin or Michigan. Pack up a car and take a roadtrip to visit the most secluded getaways from Chicago. 

RECOMMENDED: Discover more of the best day trips from Chicago

Secluded getaways from Chicago

The Saugatuck and Douglas region is mostly famous for its summertime attraction, which makes sense: With 10 spectacular miles of Lake Michigan shoreline, the sparking beaches make for a perfect summer getaway. But when winter rolls around—and the summer tourists retreat—the town takes on a new snowy sheen. Hit the slopes at nearby ski resorts like Bittersweet or Timber Ridge, book a horse-drawn sleigh ride or explore the beauty of snow-covered sand at Saugatuck Dunes State Park. At night, post up at home with a few takeaway pints from Saugatuck Brewing Company. Who ever said summer was the best season, anyway? 

Known as the “Cape Cod of the Midwest,” Door County is made up of more than a dozen small towns located on a beautiful 75-mile peninsula surrounded by the shimmering waters of Lake Michigan and Green Bay. With 53 public beaches, five state parks, and 300 miles of shoreline, there's plenty of space to get away from it all. In winter, marvel at the frozen expanses of Cave Point County Park or try cross country skiing along snow-covered forest paths. 


Sand and solitude are what you'll find at this national park in Indiana which features 15,000 acres of gorgeous nature. For hikers, there are 50 miles of trails over the park's namesake dunes but you'll also encounter wetlands, prairies, rivers and forests perfect for snowshoeing and spotting animal tracks in the snowfall. The park includes 15 miles of the southern shore of Lake Michigan; make a visit during winter months to avoid summer crowds along the beach. 

The stunning beaches of Sleeping Bear Dunes National Lakeshore should be on every Midwesterner's bucket list. The Lakeshore offers 35 miles of scenic coastline, forests and dunes in northern Michigan. For best results, wait for a weekend when the massive Dune Climb is dusted with snow, when visitors are permitted to sled down its steep expanses. Hardier folks can also try their hand at wintertime camping, which is available year-round at the Platte River Campground. 


Famous for its lakes, cranberries and the site of a notorious FBI shootout, Manitowish Waters is made up of 10 lakes and more than 4,200 acres of Wisconsin’s Northwoods. The crystal-clear waters offer an abundance of water sports, while the area in general is prime for ice fishing, bird watching, hiking, biking, and cross country skiing. Once dinner calls, head to Little Bohemia, where you can still see the bullet holes from the 1934 shootout between gangster John Dillinger and the FBI.

The city of Baraboo's claim to fame might be Circus World Museum (this is the hometown of the Ringling brothers), but you're here for Devil’s Lake State Park, located just south of the city. The largest state park in Wisconsin offers numerous hiking trails but also a number of areas for rock climbing (for visitors of any skill level), as well as eight miles of bike trails and more than 400 campsites. Come winter, it also has the best hill sledding around. 

NOTE: An annual park sticker or trail pass is required to visit state parks and trails. Buy before you go: passes are not available for purchase at the parks. Parks may also limit entrance based on capacity. 


Hoosier National Forest, in the hills of south central Indiana, offers rolling hills, back-country trails, and rural crossroad communities across 203,000 acres. Try your luck on Two Lakes Loop Trail, which features exciting rock formations, babbling rivers, and multiple campsites along the lakes. 

Need more travel inspiration?

    You may also like