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4 Best Weekend Getaways from Chicago


Nashville's nightlife lit by neon signs
Hi, I'm Alex!

Alex is a writer who has lived all over the US. More recently, he's found himself in Rhode Island, and he thinks he'll stay for a while.

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Chicago is one of the largest cities in the US, with a bustling economy, renowned museums, and an iconic skyline dotted with unique architecture and landmark buildings. But even with all the amazing things to do in this much-visited city, it’s still nice to get out of dodge for the weekend and explore the surrounding areas in the midwest. And, with indoor activities limited, it’s time to get creative on how to spend a weekend until we get back on our feet. Here’s a guide to the best weekend getaways from Chicago.


Louisville, Kentucky

Louisville's Big Four Pedestrian Bridge has amazing city views. Photo: Mitch Boehn / Unsplash

Drive time from Chicago: 4.5 hours / 300 miles (500 kilometers)

Louisville (pronounced by locals as “Loo-vill”) is a friendly city known for the Kentucky Derby race at Churchill Downs. A gathering for those to see and be seen (just look at those hats), the world-famous horse race brings tens of thousands of visitors to town each year. But it wouldn’t be a party without some good old fashioned Kentucky whisky—or Bourbon, to be specific. Yes, this area of the US is where the real-deal Bourbon is produced—similar to the Champagne region of France. Book a tour at one of the many distilleries in the area to taste first-hand why this Kentucky export is imbibed across the world. Just don’t forget to chase it with water.

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Traverse City, Michigan

Traverse City is flanked by beautiful freshwater beaches. Photo: Dennis Buchner / Unsplash

Drive time from Chicago: 5 hours / 310 miles (500 kilometers)

Up and around the “mitten” of Michigan, you’ll find this small lakeside city. Flanked by beautiful freshwater beaches on Lake Michigan and rolling vineyards, Traverse City is on the adjacent side of Lake Michigan from Chicago, yet feels worlds apart. The lake access makes for outdoor activities, like kayaking and paddleboarding, but the real takeaway is the region's wine vineyards. Yes, Michigan wine. With picturesque lake views, travel to the area’s five wineries along the Old Mission Peninsula and get a taste for the mitten terroir.

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Madison County, Iowa

The rolling farmlands and covered bridges are a sight to behold. Photo: Kelcy Gatson / Unsplash

Drive time from Chicago: 5.5 hours / 375 miles (600 kilometers)

City slickers may deem rural Iowa as “the middle of nowhere,” but Hollywood seems to have a different take. Known for idyllic covered bridges and rolling farmland, Madison County, Iowa, became famous for its depiction in the ‘90s film Bridges of Madison County —and for good reason. The covered bridges are sights to behold and tours are available to hit all the spots from the movie (Meryl Streep sighting not included). Or if you’re a sports film fan, maybe you’ll recognize the iconic house and field from Field of Dreams in Dyersville. These are landmarks of rural America, and a beautiful getaway from the hustle and bustle of the city.

Find things to do in Iowa

Nashville, Tennessee

Nashville's known for its vibrant nightlife with music flowing out of every bar. Photo: Baruch Moskovits / Unsplash

Drive time from Chicago: 7 hours / 475 miles (765 kilometers)

It always seems like a good time to visit Nashville. It’s one of America’s most musical cities and everywhere you turn, there may be a rowdy wedding party or outdoor concert. You can’t visit this city without paying homage to its country music heritage, or by visiting the famous Grand Ole Opry to play pretend superstar. Or get a taste for the city’s culture by touring all of the iconic mural art found around town. Finish off your weekend with some authentic southern barbecue before heading back north, of course.

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Hi, I'm Alex!

Alex is a writer who has lived all over the US. More recently, he's found himself in Rhode Island, and he thinks he'll stay for a while.

Keep exploring
See all Chicago tours
332 tours & tickets
Things to do in Chicago
See all things to do in Chicago
Know Before You Go: Visiting Chicago in Winter
Know Before You Go: Visiting Chicago in Winter