Summary:
Waterfalls, storybook towns, incredible food, and more await just a short drive from Chicago.
Cities can sometimes feel like endless stretches of concrete — especially in the hot summer months — and Chicago is no exception. However, there is a whole world beyond the city limits. While it doesn’t always feel like it, there are numerous worthy escapes within a few hours’ drive of Chi-town: charming towns filled with ice cream parlors, lakeside cities boasting entirely different cultures, and beautiful natural landscapes featuring waterfalls and lush trees. Waterfalls! Outside Chicago!
The Windy City’s location is an advantage. Pack your car with picnic essentials, and perhaps some hiking gear just in case, as you venture forth. You are within driving distance of several remarkable and out-of-the-ordinary places that provide perfect road trip opportunities. Here are six of them:
Madison, Wisconsin
Imagine a state known for its beer and cheese catering to over 30,000 college students; this describes the earthly delights found in Madison, Wisconsin. This state capital could stand out for its unique geography — an isthmus surrounded by two large lakes that remains beautiful even in the cold Wisconsin winters. Nevertheless, its unmatched food scene truly sets it apart for a city of its size.
The streets boast an eclectic mix of professors, politicians, businesspeople, street performers, and health enthusiasts. If you ask the locals for their favorite dining spots, you’ll likely receive diverse recommendations reflective of the city’s 250,000-plus population, including American small bites at the renowned Mint Mark, tacos and margaritas at Canteen, and Lao-Thai noodles from Vientiane Palace.
Students often recommend craft beer establishments like The Malt House or Dotty Dumpling’s Dowry, which serves one of the best burgers in town. Pair this with Wisconsin beer from New Glarus alongside some fried cheese curds for an authentic Madison experience.
Madison is about two and a half hours away from Chicago.
Starved Rock State Park, Illinois
Yes, Illinois may not be recognized for its natural beauty compared to other states. However, a hidden gem exists near the Starved Rock State Park. Visitors expecting flat farmland will be pleasantly surprised to discover an incredible valley along the Illinois River, adorned with lush trees, majestic bluffs, and 14 stunning waterfalls.
Starved Rock is an ideal destination for camping, hiking, kayaking, and white-water rafting. After a day of physical activity, you can unwind at the Starved Rock Lodge.
For a taste of local flavor, the surrounding towns offer plenty. Charming Utica hosts the August Hill Winery, along with delightful antique shops, while the historic towns of Oglesby and Ottawa are filled with Americana featuring small museums, galleries, and excellent food. Be sure to check out Red Dog Grill in Ottawa and The Rootbeer Stand in Oglesby.
Starved Rock State Park is approximately an hour and a half from Chicago.
Allegan County, Michigan
Lake Michigan is vast. When the summer heat becomes oppressive, one might be tempted to plunge into the lake in Chicago. Nevertheless, consider visiting a series of lakeside towns in Michigan that offer truly unique attractions.
Douglas, Saugatuck, Holland, and Fennville (though not directly on the water) showcase small-town charm alongside city-sized amenities. Fennville is known for its apple orchards, vineyards, and berry farms, while Saugatuck and Douglas excel as two of the Midwest’s finest lakeside towns, featuring charming downtown areas and picturesque sand dunes. A home for art enthusiasts, Ox-Bow, founded by instructors from the School of the Art Institute of Chicago, remains an artist colony on Lake Michigan’s shores.
Further up the road lies Holland, where Dutch colonists brought their rich culture, architecture, and delightful pastries. Don’t miss DeBoer Bakkerij or Veldheer Tulip Gardens, which showcases beautiful tulips.
Fennville is located approximately two hours from Chicago.
Indianapolis, Indiana
Among many types of travelers, some are captivated by urban environments and seek out exciting city life. If you identify with this group, consider a road trip from Chicago to Indianapolis. This vibrant city, the 15th largest in America, boasts a vibrant population and a calendar full of festivals, parties, and pageantry — including the famous Indy 500.
Throughout the year, Indianapolis is bustling with activity, whether you’re experiencing the dynamic IndyFringe Festival in August and September or the Wine & Food Festival in June. Additionally, the city serves as a museum hub, featuring the world’s largest children’s museum, various art institutions, and small museums honoring its local favorites, including Kurt Vonnegut and President Benjamin Harrison.
A key attraction drawing visitors to Indianapolis is its thriving food scene, which has gained national attention. Trendy restaurants such as Bluebeard, Milktooth, Crispy Bird, and Oca contribute to its reputation as a culinary hotspot, alongside long-standing establishments like Workingman’s Friend that have fed countless locals for decades.
Indianapolis lies about three hours from Chicago.
Traverse City, Michigan
If you’re in search of a true getaway, look no further than northern Michigan — still within driving distance of Chicago yet providing a wilderness-infused escape for city dwellers. Traverse City serves as a gateway to remarkable sights with small-town charm and a welcoming atmosphere. Enjoy a glass of beer or wine at popular wineries and brewpubs, such as Mari Vineyards and Mackinaw Brewing Company, before venturing into the wild.
From Traverse City’s quaint streets, you can explore the Leelanau Peninsula or head west to Sleeping Bear Dunes National Lakeshore. Taking scenic M-22 allows you to experience both stunning locations. Sleeping Bear Dunes features incredible shorelines and breathtaking sunsets that compete with any found east of the Mississippi.
Continue your journey up M-22 to discover the small-town allure of the Leelanau Peninsula, where charming towns with populations under 1,000 dot the landscape. Explore dense forests, pick apples and berries at local farms, and don’t forget to grab a hearty sandwich from the Village Cheese Shanty in Leland, whose population is a modest 377.
Traverse City is approximately five hours from Chicago.
Galena, Illinois
In rare cases, a road trip can mean traveling not just over distances but also through time. This is true when you drive west from Chicago to Galena, consistently rated as one of the best small towns in the country. Galena has worked diligently to preserve its rich history, maintaining one of the most unspoiled historic town centers in America.
The town’s prosperity began in the mid-1800s when it benefited from government grants to mine precious minerals. Since then, it has dedicated efforts to preserving its architecture from that booming era. Visitors can explore the Galena Historic District, which includes more than 1,000 buildings, such as Ulysses S. Grant’s home, showcasing the Italianate style and now serving as a memorial to his legacy. Trolley tours guide visitors to significant historical and architectural sites, enhancing the town’s nostalgic charm.
While the best dining spots might not date back to 1850, they are certainly noteworthy. Consider Durty Gurt’s Burger Joynt, established in 2007, known for its impressively stacked burgers. It appears that everyone is keen on constructing their own legacy here.
Galena is approximately three hours from Chicago.
