Spring Road Trips & Getaways Around the Midwest

If you’re in the mood to stretch out, hit the open road, and get away for a few days — or even a few hours — you’re in good company. And you’re starting from the just right place. The Midwest is full of incredible sights and one-of-a-kind destinations, many of which are just a quick car ride away from Chicagoland. 

Ready to go exploring? Here is just a small state-by-state sampling of some of the amazing Midwestern destinations within driving distance of Chicagoland, from natural wonders to cosmopolitan cities and everything in between: 


You don’t have to leave the Prairie State to have an amazing adventure. Here are a few of the incredible Illinois destinations to try out this spring: 

  • Springfield, IL. About a three-hour drive from Chicagoland, the state capital of Illinois is full of fun things to see and do. In addition to seeing the state capitol building and the Illinois State Museum in person, visitors can get a crash course in all things Honest Abe, with the Lincoln Home, the Lincoln Presidential Library and Museum, and the Lincoln Monument. 
  • Galena, IL. Visiting Galena is like stepping back in time. A few hours west of Chicagoland, Galena offers some amazing historical architecture, year-round experiences, and vineyards galore, making it perfect for a weekend road trip out of the city. 
  • Starved Rock State Park. Just about an hour and a half outside of the city you’ll find one of the best outdoor experiences you’ll find throughout the Midwest. Starved Rock State Park boasts 13 miles of hiking trails that cover all sorts of terrain, including some of the area’s most stunning natural canyons and waterfalls. Check out the lush green trees in the spring, and head back in fall for the amazing leaf colors. 
  • Shawnee National Forest. Located in Herod, Illinois — about five hours south of Chicago — is Shawnee National Forest. A go-to destination for camping, hiking, and horseback-riding, Shawnee National Forest sprawls out over more than 289,000 acres of hickory forests, wetlands, and natural canyons. 

Chicagoland Day Trips


Illinois’s neighbor to the east, the Hoosier State is full of unique towns and perfect spring destinations: 

  • Indiana Dunes National Park. Indiana Dunes is a local favorite for a reason. Just a short drive out of Chicago, this Lake Michigan staple features amazing beaches, picture-perfect natural habitats, and a ton of Midwest history. Stop by for a quick day in the Great Outdoors, or go camping for the weekend. 
  • Columbus, IN. Immortalized in a film of the same name, Columbus is one of Indiana’s hidden gems. Located about four hours away from Chicago, Columbus is home to one of the most remarkable collections of modernist architecture you’ll find anywhere in the U.S., along with great parks, boutiques, scenic hotels, and restaurants. 
  • New Harmony, IN. Talk about tranquil. New Harmony is a historic town located along the Wabash River, about five hours away from Chicago. No visit to New Harmony would be complete with a stop at its picturesque labyrinths; the striking Roofless Church; or the charming natural scenes in nearby Harmonie State Park.
  • Bloomington, IN. The home of Indiana University Bloomington, this college town features great restaurants and a variety of museums for kids and art lovers. Even better, Bloomington is a great launchpad to head out into nature, with easy access to Morgan-Monroe State Forest, Hoosier National Forest, and the Cedar Bluffs Nature Preserve. 
  • Madison, IN. Located about five hours away from Chicago by car, this Ohio River town is a classic springtime destination, with a scenic and picturesque downtown and easy access to plenty of natural excursions. Don’t forget to add the charming and historic Lanier Mansion to your itinerary. 


Just a few hours west of Chicagoland, the Hawkeye State is definitely worth exploring. Here are a few of the springtime destinations to add to your road trip itinerary this year: 


Located just north of Illinois, Wisconsin is full of amazing natural vistas, bustling cities, and quaint and out-of-the-way towns in equal measure. How many of these destinations have you visited? 

  • Milwaukee, WI. What’s not to love about Milwaukee? Located about 90 minutes north of Chicago, this Wisconsin city boasts an astonishing and architecturally significant art museum, as well as a legendary market, tons of local history, great restaurants, multiple breweries, and amazing views of Lake Michigan. 
  • Lake Geneva, WI. Conveniently located about 80 miles northwest of Chicagoland, Lake Geneva is a classic spring and summer getaway. This resort town boasts endless activities and fantastic dining, along with watersports, hot air ballooning, and more. 
  • Horicon Marsh. Want to get up close and personal with wildlife? The Horicon National Wildlife Refuge, located about two and a half hours northwest of Chicagoland, has been called one of the nation’s best spots for birding. You’ll also spot small mammals and plenty of reptiles and amphibians while enjoying recreational activities such as fishing, biking, paddling, and cycling. 
  • Door County, WI. A four and a half mile drive from Chicagoland, Door County has been called the “Cape Cod of the Midwest.” This collection of picturesque small towns offers great dining and nightlife, while also putting you in the heart of nature — with hundreds of miles of shoreline, dozens of public beaches, five state parks, and amazing outdoor attractions. 


The Great Lakes State, Michigan offers springtime travelers plenty of wonderful things to see and do. Best of all? It’s all just a short trip away from Chicagoland! Try out these Michigan road trip destinations for a fun and unique spring adventure: 

  • Holland, MI. No, you didn’t get whisked away to Europe, thought it can be hard to tell the difference when you’re in Holland, Michigan. Located approximately two hours northeast of Chicago, Holland boasts an amazing old world lighthouse and windmill, and is the home of a much-beloved tulip festival, harkening back to the area’s Dutch roots. Enjoy some outdoor time in Holland State Park and the Windmill Islands Gardens. 
  • Traverse City, MI. Located on the far northeastern point of Michigan, about five hours away from Chicago by car, Traverse City has just about everything you could possibly want in a resort town, including plenty of gorgeous beaches, great restaurants, and even a world-renowned film festival. 
  • Ann Arbor, MI. Charming and bustling in equal measure, Ann Arbor is a prime weekend destination about four hours away from Chicagoland. Perhaps best known as the home of the University of Michigan, Ann Arbor is also a foodie’s delight, with plenty of breweries, sweet shops, and amazing local eateries. Don’t forget to stop by the Museum of Natural History or the Ann Arbor Hands-On Museum. 
  • Saugatuck, MI. About a two hour drive from Chicagoland, Saugatuck is nestled between Lake Michigan’s eastern banks and the picturesque Kalamazoo Lake. This means that lovers of all things aquatic are sure to find something to do; the area also boasts great hiking and outdoor exploration at Mt. Baldhead, as well as thriving dining and art scenes. 


Just southwest of Illinois is Missouri. They call themselves the Show-Me State, and you’d better believe there’s plenty to show off — historical sites, restaurants, natural areas, and everything in between:

  • Route 66. Have you ever heard of Route 66? This iconic American roadway helps connect Chicago to St. Louis, Missouri. A scenic drive and getaway in its own right, this famous journey also features plenty of amazing places to stop off, including the Chain of Rocks Bridge in Missouri, which is on the national register of historic places.
  • St. Louis, MO. A perfect weekend trip, St. Louis is just about five hours away from Chicago by car. In addition to the world-famous Gateway Arch, spend some quality time outdoors at the Missouri Botanical Garden and Forest Park. Feast on barbecue in the Soulard District, and do some exploring along the banks of the Mississippi River. 
  • Kansas City, MO. Seven hours away from Chicagoland by car, Kansas City is a fun escape, featuring plenty of amazing eats and wonderful attractions, including the Kansas City Zoo, the Nelson-Atkins Museum of Art, and the Worlds of Fun Amusement Park.

When Home Means More, You Need a Team With More to Offer

Home is about so much more than just four walls. Buying or selling a home is a big deal, and with everything we experienced in 2020, our homes have never been more important. That’s why your local Baird & Warner agent is with you at every step of the way, from finding the perfect home to connecting you with local experts in mortgage and title. Whether it’s the beginning of a story or the end of a chapter, we’re here to help — so you can get back to planning your next great adventure in no time.