The Best Day Trips Around Chicago, IL

The Chicago area offers a wide variety of delights, but restless residents may crave an escape from the familiar hustle and bustle. Fortunately, the surrounding area features several delightful destinations perfect for a memorable day trip. We’ve rounded up several outstanding options for relaxation and entertainment within a few hours of Chicago.

Holland, Michigan

by Erik Cooper is licensed with CC BY 2.0

About two-and-a-half hours from Chicago, Holland, Michigan, is a charming destination that feels a world away. This city’s rich Dutch heritage is evident everywhere you turn. The Windmill Island Gardens are built around a 250-year-old Dutch windmill. The gardens feature dozens of flowers, including 100,000 tulips that put on a stunning display each spring. The Windmill Island Gardens also feature an antique Dutch carousel, a Little Netherlands village, and a “Four Columns” street organ from Amsterdam.

Holland may seem small and quaint, but there’s plenty to do. Get a taste of the Netherlands with a fresh loaf of Dutch currant bread from deBoer’s Bakkerij, sample cask-poured stouts at New Holland Brewing, or visit the Big Red Lighthouse. If you visit in springtime, you can partake in the Tulip Time Festival and view over five million blossoms at the Veldheer Tulip Gardens. This is truly a breathtaking place to go.

Gurnee, Illinois

Gurnee, Illinois, just an hour from Chicago, offers a diverse range of attractions. Top among them is Six Flags Great America, which offers thrill rides, family rides, and live entertainment. For watery fun, head to the Great Wolf Lodge, which features an 80,000-square-foot indoor/outdoor water park and a 40,000-square-foot adventure park with a climbing wall, ropes course, arcade, and more.

If you have a sweet tooth, you won’t want to miss the Chocolate Sanctuary, which features a fascinating menu that incorporates chocolates in several unexpected places. You’ll find cocoa-candied bacon on the Sanctuary burger, chocolate vinaigrette atop the Sanctuary chopped salad, and a cacao nib crust on the salmon. You’ll never look at chocolate the same way again.

Milwaukee, Wisconsin

Just 90 minutes from Chicago, Milwaukee is accessible by car and via Amtrak. This historically German city has several brewpubs and microbreweries that do an admirable job of keeping its heritage alive. The Milwaukee Public Market is a must for foodies, offering an abundance of ethnic artisan products and ready-to-eat delights from shops such as the West Allis Cheese & Sausage Shoppe, St. Paul Fish Company, The Green Kitchen, and C. Adam’s Bakery.

You can work off some of your indulgences at the 22-acre Lakeshore State Park. Adjacent to the park, you’ll find the Henry W. Maier Festival Grounds, which hosts many of the annual events the city is known for. Dubbed Festival City, Milwaukee always seems to have something going on. You’ll find German Fest in July, Irish Fest in August, Indian Summer Festival in September, and much more. Check the calendar before your visit so you don’t miss a thing.

Michigan City, Indiana

Michigan City is just about an hour and 15 minutes from Chicago via car or Amtrak. Indiana Dunes National Park is one of the city’s prime highlights, offering 15 miles of sandy shoreline along Lake Michigan. Swimming and sunning are popular summer diversions, but this park also offers plenty of other highlights. If you’re tired of Chicago’s hiking trails, you can explore 50 miles of new routes throughout the park. Visitors can also explore historic 19th-century buildings or take the kids to the park’s Nature Play Zone.

Washington Park offers a picturesque stretch of shoreline that’s perfect for a picnic. The nearby Washington Park Zoo and Old Lighthouse Museum provide additional entertainment. For lovely views and lakefront delights, this is a wonderful place to visit.

Oak Park, Illinois

Just 30 minutes from Chicago, Oak Park is an excellent choice when you want a shorter drive and plenty of time to enjoy your destination. This historical area features the homes of both Ernest Hemingway and Frank Lloyd Wright. These have given rise to attractions like the Frank Lloyd Wright Home & Studio and Ernest Hemingway Birthplace and Museum. Taking in the sights, you’ll also see several homes and buildings designed by architect George W. Maher.

Oak Park is the type of place that you’ll always want to visit hungry. Treat yourself to fine dining at Rustico, where you can enjoy gourmet delights, such as salmon in caperberry brown butter sauce or black truffle and potato gnocchi with wild mushrooms. For something more casual, hit Firecakes for small-batch, scratch-made donuts, or sample the brews at Kinslahger Brewing Company. Whatever you’re craving, you’re sure to find something in this town to satisfy.

Cedarburg, Wisconsin

When you want a quiet escape from the bustle of Chicago, head to Cedarburg, just two hours away. This quaint destination has a distinctly small-town atmosphere, but that doesn’t mean that there’s a shortage of things to do. The historic Hilgen & Schroeder Mill Store houses the Cedarburg Visitor Center as well as the Cedarburg History Museum. For a taste of the town’s current culture, head to the Cedarburg Cultural Center, where you can find local art, live music, and theatrical performances.

Enjoy rustic dining at The Farmstead, a quaint restaurant housed in a 150-year-old farmhouse. One of the newest establishments in town, the Union House is located in a similarly historic building, first constructed in 1883. Here, you’ll enjoy tapas-style dining that lets you sample several savory delights, including bourbon meatballs, baked goat cheese, garlic shrimp, BBQ pork ribs, and more.

Make sure you stop by Amy’s Gourmet Apples for a sweet treat to complete your day. Carmel apples get a whole new flavor here with a second coating of decadence in the form of white, milk, or dark Belgian chocolate over the caramel and embellishments, such as sprinkles or sea salt, on top.

Do you know of other outstanding road trip destinations around Chicago? Share your recommendations with our team at Gurnee Podiatry & Sports Medicine. We love having the best suggestions in town for our clients.