The 5 Best Midwest Stops Sandwiched Between Chicago And Indianapolis

Midwestern road trips aren't usually the ones that people are writing home about. They're often overlooked for other great American traverses, like California's Pacific Coast Highway or Colorado's Million Dollar Highway. But, middle America's highways were built to connect a series of vibrant towns that bridged the east coast to the west, which brought a mixture of influences and cultures to its cherished small-town destinations. They've now grown to be well-known tourist attractions, particularly those sandwiched between Chicago and Indianapolis.

The commute between these two reputable cities takes anywhere from 3 to 3.5 hours one way, making it easy to fit in a side-destination on a day trip. And, if you have the time, many of these Midwest stops are worth a day or two of exploration.

While there are dozens of interesting roadside attractions along the way, these five key cities are worth checking out, ideal for a quick lunch or a side trip in and of themselves. These stop-worthy destinations are either along the path to Chicago or Indianapolis or a short detour off the main route, giving you the most touristic exposure without pulling you too far off the highway.

Chesterton, Indiana is your first stop out of Chicago, about an hour's drive south of the city, and it only adds about 20 minutes to the overall commute. Coming from Indianapolis, the town is just over a 2.5-hour drive away. It's a reasonable distance for road trippers who want to spend an afternoon or longer in the tight-knit, artsy town. Chesterton is home to only 15,000 full-time residents, but the locale feels dense, vibrant, and touristic to visitors. The town's center features rows of boutique shops, retro toy outfitters, and Amish furniture makers, all within walking distance.

Yesterday's Treasures Antique Mall is a great place for visitors to meet locals, with 75+ vendors in a 20,000-square foot venue where you'll find handcrafted goods, vintage gems, and rare collector's items. The Chesterton European Market brings commerce outdoors with curious items for sale alongside freshly-cooked and baked goods. Artists and art lovers should peek into the Chesterton Art Center, a town staple that always features a rotating roster of exhibitions and creative workshops for all skill levels and ages.

One of Chesterton's biggest draws is its easy access to the Indiana Dunes National Park, a protected shoreline and forest with 16,000 acres of natural beauty, 50 miles of dune trails, and 15 miles of scenic Lake Michigan views. This stunning attraction is a less than 10 minute drive from town and is the perfect stop between Chesterton and Chicago for those looking to stretch their legs.

Indiana's wildly underrated beach town, Michigan City, gets its name from the great lake, not the state itself. It is a scenic stop just over an hour from Chicago, and under three hours from Indianapolis. The shoreside town is a popular starting point for adventures at Indiana Dunes National Park, and a drive to its boundaries takes less than 10 minutes.

Washington Park is the star attraction of the town itself, housing the historic Michigan City Lighthouse, a swimmable beach, and an active marina. One visitor states that the park is ideal for those hoping to catch a meal from the waters, mentioning they've: "seen people have good luck catching salmon there! Bring salad shrimp & good fishing!"

Outside its stunning natural attractions, the town itself has plenty to explore, with a history stretching back to 1836 when its commercial district was first incorporated. The Elston Grove Historic District, Haskell and Barker Historic District, and Franklin Street Commercial Historic District take visitors back in time with stately 19th century architecture, some of which are on the National Register of Historic Places. Modern attractions include artistic hotspots, like the Canterbury Theatre and Lubeznik Center for the Arts. Families can enjoy a variety of museums, such as the HEROS: Superhero Museum and Hesston Steam Museum.

Culver has gained its reputation as the Cape Cod of the Midwest for good reason. The quaint town is approximately halfway between Chicago and Indianapolis, about two hours from either city, making it the perfect midpoint stop on your drive. While this road trip destination is inland, it sits on Lake Maxinkuckee, a popular spot for paddle boarding, kayaking, and various marina services, located in the heart of downtown.

One of the best ways to explore the town is by bike, so if you're carrying any on your vehicle en route to Chicago or Indianapolis, make sure to take advantage of the 10-mile city loop that hugs the beach and passes through maple-dappled forests. Popular museum stops include the Crisp Visual Art Center and Culver Academy Museum, with one featuring an expansive art collection and the other reflecting Culver's past through rare artifacts.

Culver's Main Street is nestled along Lake Maxinkuckee's shore, with direct access to the public beach and its many festivals, such as the annual Culver Winter Fest. While strolling the town's center, check out local favorites, like the eclectic boutique, The Collective, and the walk-in Earthwerks Ceramics Studio. For a bite to eat, visit Lakehouse Grille or Lake Max Beach Bar for year-round waterfront views.

As the home of Purdue University, Lafayette is a one of the fastest-growing metro areas in America, with plenty of entertainment for travelers making their way along I-65. The commute is just under 2.5 hours from Chicago and approximately 1.5 hours from Indianapolis. Though the town only boasts a population of about 4,600 people, the bustling Purdue University regularly brings in crowds when class is in session.

The city is brimming with art, and with a Public Art Trail guide in hand, visitors can tour over 125 works that are easily accessible by foot, bike, or car. There's also a burgeoning, fairly walkable beer scene in town, with locales like People's Brewing Company & Taproom and Brokerage Brewing Company cultivating people-first spaces that are great for meeting fellow tourists and Lafayette residents alike.

For a quick burst of excitement for young travelers and families, stop by Malibu Jack's indoor amusement park, the largest in the state, open rain or shine. The Columbian Park Zoo is another popular family stop, with stand-out exhibits, like the Butterfly Garden and Penguin Cove. From there, explore the additional 40 acres of Columbian Park, featuring an outsized playground, event-filled amphitheater, and trail system within its parameters.

Considered by many to be Indiana's most charming small town, Zionsville contrasts the hustle and bustle of Indianapolis with its quaint charm and stunning green spaces. It's about half an hour away from Indianapolis and just under three hours away from Chicago. Its Main Street clusters unique shops, cozy restaurants, markets, and cafés for visitors to enjoy during a day trip or longer. 

The town is a popular autumn destination, featuring the annual Zionsville Fall Festival with vendors, amusement rides, and live music. For more laid-back leaf peeping, the 80-acre Starkey Nature Park offers hiking trails, fishing opportunities, and amenities, like picnic tables, in its densely wooded bottom land. For a quicker road trip stop, the Zionsville Nature Center is an excellent, family-friendly choice, with a strong curation of wildlife exhibits and regular educational workshop opportunities. 

If you're traveling with your clubs on hand, consider a nine-hole round at Zionsville's Golf Course, open to guests in the warmer months. For cultural options, artistically-inclined travelers can stop by a handful of galleries featuring the works of local creatives, such as Out of the Blue and the co-operatively-owned Art in Hand gallery. History buffs will enjoy the quirky Antique Fan Museum, a unique collection of over 2,000 fans dating back to the 1890s. The Sullivan Munce Cultural Center is a great spot for learning about the town's unique history, paired with genealogy research and local art.

All references and recommendations in this article were meticulously researched and vetted by our team to ensure complete accuracy and help travelers plan their trip smoothly. We consulted with online business directories for the most recent information about local commerce. Municipal government and local tourism boards provided details on major attractions in the area, ranging from natural landmarks to downtown districts. 

We then reviewed dozens of tourism insights and recommendations from Reddit, we pulled the most useful comments for consideration when deciding the best five destinations to recommend. Most importantly, we verified that each stop actually qualified as a convenient side trip between Chicago and Indianapolis, making sure that all above-mentioned towns were easily accessible on a day drive between the two major cities.