9 of the Best Road Trip Destinations from Chicago

best road trips from Chicago
Traverse City, MI
best road trips from Chicago
Traverse City, MI

There is something innately American about road trips. In our country’s early years, pioneers embarked on travels through the Wild West, romanticizing ideas of adventure and opportunity. Today, nothing facilitates our preoccupation with the open road like a powerful car and a gracious speed limit. On the welcome path is a weekend pass to follow our own purgatives, freed from our daily routine.

Take your place among a throng of adventure hungry drivers this weekend. There’s a route out there waiting for you. Here are my favorite road trip paths from Chicago.

(Of course, you could just stay home and make it a staycation type of weekend. Totally up to you, boo.)

best road trips from Chicago
Mackinac Island, MI

Indiana Dunes National Lakeshore (1 hour)

Sand dunes as tall as buildings and a spacious sandy beach provide a welcome retreat from the concreate jungle of ChiCity. Come here to hike up and then tumble down the dunes, swim Lake Michigan, fire up the grill, and campout.

There isn’t a whole lot more to do here, however. If you’ve got the time, drive a little farther to one of the other options below.

Geneva, IL & St. Charles, IL (1 hour)

These two towns are, in a word, quaint. If you’re visiting one, you may as well stop by the other.

In St. Charles, the streets are lined with old-fashioned homes; some lived in, others converted into equally antiquated stores. It’s a great city to arrive to by Metra and tour by bike.

Geneva is a picturesque place, big on al fresco dining along the Fox River. Work rats come here to overdose on suburban living before scurrying back to their loft apartments in the big city.

What to do in Milwaukee this weekend
Milwaukee, WI

Milwaukee, WI (1.5 hours)

“The way Chicago views Milwaukee can best be compared to how we as a nation view Canada. ‘It’s extremely cold way, way up there. The people, who are refreshingly friendly, talk funny and smile too much. It’s basically the miniature version of us, right?’”  – Where Chicago Goes: 48 Hours in Milwaukee.

For Chicagoings.com’s Where Chicago Goes series, I recently partnered with Milwaukee’s tourism board to create a full and detailed guide of the city for any Chicagoans who may wander there from time to time. See that complete guide here.

Lake Geneva, WI (1.5 hours)

For all those new to the Midwest, no. This is not the same as Geneva. This is LAKE Geneva. The difference? Still quaint, this is actually a resort town, built for tourism. Enjoy golfing, horseback riding, strolls along the beach, and anything else you imagine your parents might be into – or, perhaps, your grandparents. True, Lake Geneva wasn’t built for Millennials but we love the less crowded waters which are perfect for sailing.

best road trips from Chicago
Mackinac Island, MI

Madison, WI (2.5 hours)

This is a college town. Period. It breathes Badgers. It eats Badgers. It sleeps Badgers. The state capital quivers with excitement (truly, it shakes a bit) on game day. Unlike the obnoxious dopes you’ll find littered around the streets of other school-centric cities, Madison people are kind of charming – in fact, they’re really charming.

Chris Farley was born here. The Onion was born here. You’re already in Madison’s debt based on the weight of those two things alone. Get up there and show your appreciation with a weekend full of brats and beer – and Badgers!

Saugatuck, MI (2.5 hours)

Full disclosure: I’ve never been here but I hear it has the absolute best beach in the Midwest. Rent a boat and hop in the water. When you’re done, take a tour at the Saugatuck Brewing Company.

Door County, WI (4 hours)

The peninsula of Door County is a romantic little thumb of an oasis that deserves all of the attention it receives, and a little more. Known for its sweet wines, there’s really no better place to shoot the breeze with the one you love in the Midwest. Enjoy a fish boil along the water and make the night even sweeter with a slice of Door County cherry pie. Fresh cherries from one of the town’s orchards are everywhere and in everything here.

best road trips from Chicago
Traverse City, MI

Traverse City, MI (5 hours)

For the distance you have driven, you shall be rewarded. In Traverse City you’ll find the best of every getaway destination mentioned above, and then some. It has fresh cherries, high sand dunes, beautiful waters, kitschy antiques, and a charmingly hospitable group of residents. What’s more, Mediterranean style vineyards are peppered with mansions and homes turned bed and breakfasts. This is where we come to feel the farthest away from our real lives.

Mackinac Island, MI (6.5 hours + 30 minute ferry)

If you’re running from the law, a demanding workload, or you just want to feel like you’ve completely fallen off the planet into a hole unbound by time or space, come to Mackinac. The town is aggressively historic. No cars. No real hotels. No problems. Stay at one of the island’s many B&Bs (but do your research first!) and call a cab to the coast. The cabs are, of course, all horse and buggy driven because everything here is super cute for no reason. During the right season, fresh lavender is everywhere and Mackinac Island literally smells like romance. Oh, don’t forget to bring home some fudge.