7 Perfect Weekend Road Trips from Chicago

7 Perfect Weekend Road Trips from Chicago

Even the most loyal city folk among us sometimes yearn for fresh air, open road and the charm of a small town.

Chicago is, no doubt, one of the best cities in the world and Windy City natives will most certainly be the first to tell you that.  We love our expansive lake views, our glorious skyline, our funky neighborhoods and our deep dish pizza.  But we’re not immune from a little urban overload once in a while.

And more often than not the cure is simply a few days away, preferably somewhere we can get to in just a few hours in the car.

Fortunately, there are a wealth of beautiful towns with interesting culture within a few hundred miles of The Loop.  So, choose a weekend, play hooky on Friday, leave right after rush hour dies down and be somewhere new in time for lunch.

  1. Door County, Wisconsin

Drive Time:  4 Hours

Claim to Fame:Sometimes referred to as the “Cape Cod of the Midwest,” this quaint and beautiful area is home to a whopping 12 lighthouses, all of which were built in the 19th century and beautiful to behold any time of the year.

Don’t Miss:Check out their local wineries and the bustling cherry trade.  The area is known for the tart fruit so try your hand at cherry picking in the late summer and early fall or just enjoy the many cherry treats while you’re there.

  1. Lake Geneva, Wisconsin

Drive Time:  1.5 Hours

Claim to Fame:The beautiful lake town has long been an upscale retreat for wealthy Chicago dwellers the likes of Hugh Hefner, William Wrigley Jr., and many other big industry barons looking to escape the city.

Don’t Miss:Beautiful, luxurious and pampering resorts and spas abound in Lake Geneva so head here when you’re ready to splurge on high end accommodations that come with the best in amenities.  Try the Grand Geneva or Geneva Ridge and stock up on your rest and relaxation.

  1. Saugatuck-Douglas, Michigan

Drive Time:  2.5 Hours

Claim to Fame:There are a couple actually – the pristine Oval Beach on Lake Michigan made it toCondeNaste Traveler Magazine’s list of the 25 best shorelines in the world and Saugatuck was just recently named the Best Small Coastal Town in the whole country by USA Today.

Don’t Miss:The area is known for its thriving art community, so be sure to check out some of the galleries as well as the historic Oxbow artists’ residency and the regular gallery stroll events with live music.  And if art isn’t really your scene, then head to one of the acclaimed wineries or local craft beer maker,  Saugatuck Brewing Company.

  1. Galena, Illinois

Drive Time:  3 Hours


Claim to Fame:Named by Trip Advisor as one of America’s Top 10 Charming Small Towns, Galena is all about the cobblestone streets and lovely, historic mansions.  In fact, over 85% of its buildings from the 19th century have made it to the National Register of Historic Places.  History buffs will also appreciate the fact that Galena is home to a former residence of Ulysses S. Grant.

Don’t Miss:In the winter, the area’s many hills make it perfect for skiing and in the summer, be sure to check out the picturesque views overlooking the Mississippi River.

  1. Traverse City, Michigan

Drive Time:  5 Hours

Claim to Fame:This Western Michigan beach town has become well known as a food and wine lover’s paradise.  Its 30 wineries, 16 microbreweries and many gourmet restaurant is what made Bon Appetit Magazine name Traverse City in its Top 5 Foodie Towns.

Don’t Miss:Balance out your food & wine tour with some breathtaking nature in nearby Sleeping Bear Dunes National Park and a show or a tour at the Interlochen Center for the Arts.

  1. New Glarus, Wisconsin

Drive Time:  2.5 Hours

Claim to Fame:Though the town calls itself “America’s Little Switzerland,” it’s probably better known for the New Glarus Brewing Company, a microbrewery that’s so micro it’s not distributed anywhere outside of Wisconsin.  That’s why many visitors bring back a few six-packs of the brewery’s most popular brew, Spotted Cow, whenever they visit.

Don’t Miss:  For a fun step back in time and a look into the town’s European roots, check out the Swiss Historical Village.

  1. Starved Rock State Park, Illinois

Drive Time:  1.5 Hours

Claim to Fame:Just a hop, skip and a ride from the bustling Chicago streets is a natural paradise that seems like worlds away from city life.  The park is known for its secluded hiking trails, striking canyons and gorgeous waterfalls.

Don’t Miss:Reward yourself for all that rigorous hiking with a slight change of pace at one of the area’s wineries, like August Hill or Illinois River.

Though we sometimes think of Chicago being the only star of the Midwest, it’s easy to see that there are many other noteworthy destinations that are just up the road.  And they’re all absolutely ideal for a quick jaunt and a much-needed respite from the chaos of city life.


About the Author:  Jay Deratany is a proud Chicagoan who loves exploring the Midwest whenever he can.  His favorite destination is the Saugatuck-Douglas area of Michigan – in fact, he loves it so much that he decided to open a hotel there.  The Kirby is housed in a historic Victorian mansion that used to be a well-loved Saugatuck Bed and Breakfast, but it’s been revamped as a luxury boutique hotel and gourmet restaurant.  To learn more & make a reservation, visit www.thekirbyhotel.com.



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