The 9 Best Road Trips to take from Chicago in 2019

Enough time for a getaway but too brief to travel too far, three-day weekends were made for road trips. No matter where you call home, but especially here in the Midwest, 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 prerogatives, freed from our daily routine.

In my 20’s, road trips were all about parties and making new friends. These days I’m all about romance and relaxation. Whatever you’re looking for, there’s a route out there waiting for you. Here are 9 of the best road trips to take from Chicago, in order of distance.

The 9 Best Road Trips to take from Chicago in 2019

Indiana Dunes National Lakeshore (1 hour)

Dunes as tall as buildings and a spacious sandy beach provide a welcome retreat from the concrete jungle. A constant war between winds and waves create these unique formations naturally. The result is a landscape unlike any in the world, and it’s only an hour’s distance from Chicago. Invite a few friends for a cookout and beach games, or hike up and then tumble down the dunes, swim Lake Michigan, and campout.

Got more time? Drive a little farther to Geneva.

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

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

By design, St. Charles is lined with historic homes; some lived in, others converted into tchotchke shops. Get here by Metra (Chicago’s commuter train) and tour by bike. Pick up a few yellowed books and refined home goods.

Geneva is picturesque, big on al fresco dining along the Fox River. It’s pride, though, is Fabyan Windmill, an authentic, working Dutch windmill first erected in the 1850s before it was relocated, restored, and reassembled in Geneva.

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 admittedly friendly people talk funny and smile too much. It’s basically the miniature version of us, right?”  – Where Chicago Goes: 48 Hours in Milwaukee.

Milwaukee’s my hometown, but my 10-year-old self would barely recognize it these days. Thanks to prohibition era lounges, farm-to-table restaurants, popular brewery tours and festivals, the city’s cooler than I remember.

Tour the Harley Davidson Museum. Even if you’re not into motorcycles, you’ll be captivated by the history and artisanship.

Featured in everything from Victoria’s Secret commercials to blockbuster films, the Milwaukee Art Museum is just as seductive outside as the art it holds inside. Designed by Spanish architect and sculptor Santiago Calatrava, it resembles both a bird and a boat, sitting on Lake Michigan with pride and majesty. The “wings” even flutter on schedule.

Don’t miss a lively tour at Lakefront Brewery. There’s beer, bangers, and gut-busting tour guides.

In the center of it all is the Milwaukee River, where you can watch the folk above while floating on a kayak without a care in the world. I recommend the Milwaukee Kayak Company.

Lake Geneva, WI (1.5 hours)

Not to be confused with the Geneva mentioned above, this is Lake Geneva. The difference? Still quaint, Lake Geneva is 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. No one built Lake Geneva for the under-35-year-olds, but I love the less crowded waters which are perfect for sailing.

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 charming and welcoming.

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 the attention it receives, and a little more. There’s no better place to canoodle with the one you love than in a town famous for sweet wine. Enjoy a fish boil along the water and make the night even more delicious with a slice of Door County cherry pie. Fresh cherries from one of the town’s orchards are everywhere and in everything here.

Traverse City, MI (5 hours)

For the distance you have driven, you shall be rewarded. Traverse City is a pill made of the best from each destination above. It has fresh cherries, high dunes, beautiful waters, kitschy antiques, and a charmingly friendly group of residents. What’s more, Mediterranean-style vineyards are peppered with mansions and homes turned into bed and breakfasts. Here is where I come to feel the farthest away from home.

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

If you’re running from the law, a demanding workload, or you 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 smells like romance. Oh, don’t forget to bring home some fudge.