Day Trips from Chicago by Train, Bus, or Car: Midwestern Hidden Treasures
Chicago is an incredible city, but sometimes, a quick escape is just what you need. Fortunately, the Midwest is packed with hidden treasures, all within a few hours of the Windy City. Whether you’re looking for historic towns, scenic landscapes, or charming small cities, you can get there by train, bus, or car—no hassle required.
From quaint waterfront towns to outdoor adventures and cultural gems, these day trips promise a refreshing break from city life. Pack a bag, grab your favorite road trip playlist, and get ready to explore some of the best getaways just outside Chicago.
Milwaukee, Wisconsin – Beer, Art, and Lakefront Views
Just 90 minutes by train on the Amtrak Hiawatha, Milwaukee is a fantastic mix of big-city culture and small-town charm. Stroll along the Milwaukee RiverWalk, explore the stunning Milwaukee Art Museum, and grab a fresh pint at one of the city’s famous breweries like Lakefront Brewery. If you’re visiting in summer, don’t miss Summerfest, one of the largest music festivals in the world.
For a more relaxed vibe, head to the Historic Third Ward, filled with boutique shops and cozy cafés. If you’re a baseball fan, catch a Milwaukee Brewers game at American Family Field. Milwaukee’s blend of culture, food, and lakefront scenery makes it one of the easiest and most rewarding day trips from Chicago.
Starved Rock State Park – Breathtaking Canyons and Waterfalls
Just a 90-minute drive southwest, Starved Rock State Park is a paradise for nature lovers. With 18 scenic canyons, gorgeous waterfalls, and miles of hiking trails, it’s a perfect spot to escape the city’s hustle. Visit in spring or after heavy rain to see the waterfalls at their most impressive.
Pack a picnic or stop by The Lodge Restaurant for a hearty Midwestern meal after your hike. If you prefer a more relaxed experience, take a guided boat tour on the Illinois River, where you might spot bald eagles soaring overhead.
Holland, Michigan – Dutch Charm on Lake Michigan
Just under three hours by car, Holland, Michigan, feels like stepping into a European village. Famous for its Tulip Time Festival in May, this town bursts into color with millions of blooming tulips. Even outside the festival, you can explore the charming downtown area, with boutique shops and Dutch-inspired eateries.
For a beach day, head to Holland State Park, where you’ll find stunning views of Big Red Lighthouse and Lake Michigan’s sandy shores. Don’t forget to stop by Windmill Island Gardens, home to an authentic 250-year-old Dutch windmill.
Oak Park, Illinois – Frank Lloyd Wright and Literary Legends
A quick 20-minute train ride on the Green Line takes you to Oak Park, a town rich in architectural and literary history. Visit the Frank Lloyd Wright Home and Studio, where the legendary architect developed his groundbreaking designs. Take a self-guided walking tour to admire the many Prairie School-style homes scattered throughout the neighborhood.
Oak Park is also the birthplace of Ernest Hemingway. Stop by the Hemingway Birthplace Museum to learn about his early years before heading to one of the town’s cozy cafés for a relaxing afternoon.
Lake Geneva, Wisconsin – A Waterfront Escape
Less than two hours by car, Lake Geneva is the perfect spot for a scenic lakefront getaway. The highlight is the Geneva Lake Shore Path, a 26-mile walking trail offering stunning views of historic mansions and crystal-clear waters. If you’re not up for the full hike, even a short stroll along the path is breathtaking.
For a unique experience, take a Lake Geneva Cruise to learn about the area’s fascinating history while soaking in the views. In the winter, the town transforms into a cozy holiday retreat, with festive markets and ice castles.
Michigan City, Indiana – Beaches, Shopping, and History
Just an hour by train on the South Shore Line, Michigan City is an easy escape with a little bit of everything. Spend the day at Indiana Dunes National Park, where you can hike scenic trails or relax on the sandy beaches along Lake Michigan.
If shopping is more your style, check out the Lighthouse Place Premium Outlets for some great deals. Before heading back, stop by Washington Park Lighthouse, a historic landmark offering some of the best sunset views in the area.
Galena, Illinois – A Historic Gem with Small-Town Charm
A three-hour drive west brings you to Galena, a beautifully preserved 19th-century town known for its rich history and charming downtown. Wander through the Main Street boutiques, visit the former home of Ulysses S. Grant, and explore the scenic hills and vineyards surrounding the area.
Wine lovers will enjoy a tasting at Galena Cellars Winery, while outdoor enthusiasts can kayak on the Galena River or hike in Horseshoe Mound Preserve for breathtaking views. Galena’s slower pace and timeless charm make it a wonderful retreat from city life.
Springfield, Illinois – Lincoln’s Legacy and More
Hop on an Amtrak train for a three-hour ride to Springfield, the hometown of Abraham Lincoln and a must-visit for history buffs. The Abraham Lincoln Presidential Library and Museum is an interactive and engaging way to learn about one of America’s greatest leaders.
Take a tour of Lincoln’s Home National Historic Site, then grab a classic horseshoe sandwich—a local favorite. If time allows, stroll through the Illinois State Capitol, which boasts stunning architecture and fascinating history.
Rockford, Illinois – Gardens, Museums, and Outdoor Fun
Just an hour and a half by car, Rockford offers a mix of nature, culture, and family-friendly attractions. Visit the stunning Anderson Japanese Gardens, one of the most beautiful Japanese gardens in the U.S., or explore the Discovery Center Museum, perfect for kids and curious adults.
If you’re an art lover, don’t miss the Rockford Art Museum, showcasing a mix of contemporary and regional works. Wrap up your day with a scenic walk along the Rock River Recreation Path before heading back to the city.
