Chicago is a bustling city with plenty to do and see, but sometimes you need to escape the urban sprawl and hit the open road. Luckily, there are plenty of fantastic road trip destinations within easy driving distance of the Windy City. Whether you’re looking for outdoor adventure, small-town charm, or big-city excitement, there’s a perfect road trip waiting for you.
1. Milwaukee, Wisconsin
Just a short 90-minute drive north of Chicago lies Milwaukee, Wisconsin’s largest city.
Known for its beer culture and stunning lakefront views, Milwaukee is an excellent destination for a quick getaway. Take a brewery tour at MillerCoors or Lakefront Brewery or visit the Harley-Davidson Museum to learn about the iconic motorcycle brand’s history. Don’t forget to grab some cheese curds – a Wisconsin staple!
2. Galena, Illinois
If you’re looking for small-town charm and beautiful scenery, head west to Galena, Illinois.
This historic town is known for its 19th-century architecture and picturesque downtown area. Take a hot air balloon ride over the rolling hills of Jo Daviess County or explore the quaint shops and galleries on Main Street.
3. Mackinac Island, Michigan
For a longer adventure (about 6 hours from Chicago), head north to Mackinac Island in Michigan’s Upper Peninsula. This car-free island is accessible only by ferry or plane and offers stunning natural beauty and plenty of outdoor activities such as hiking and biking trails around the island’s perimeter.
4. Indianapolis, Indiana
If you’re looking for big-city excitement without venturing too far from home (about 3 hours from Chicago), Indianapolis is an excellent option. Home to world-class museums like the Indianapolis Museum of Art and the Children’s Museum of Indianapolis as well as sporting events like the Indy 500 at the famous Indianapolis Motor Speedway, there’s something for everyone in this vibrant Midwestern city.
5. Door County, Wisconsin
Located about 4 hours north of Chicago, Door County is a popular summer destination for Midwesterners. With charming small towns like Fish Creek and Ephraim, beautiful beaches along Lake Michigan, and plenty of outdoor activities like kayaking and hiking, Door County is the perfect place to unwind and reconnect with nature.
No matter where your road trip takes you from Chicago, make sure to pack plenty of snacks, drinks, and good music – the journey is just as important as the destination!