Most Popular Day Trips from Chicago, Illinois

Have a few extra days in Chicago? Give yourself a break from the Windy City on some of the best day trips from Chicago, Illinois!

From charming towns like Michigan City to architectural hubs like Oak City to natural paradises like Lake Geneva, the area around Chicago is bursting with variety. All located just a couple of hours max from the city, these side trips can offer a reprieve from Chicago’s hustle and bustle and show you a different side of the Midwest.

Ready to explore more of the Great Lakes area? Throw some of these outstanding Chicago side trips into your itinerary.

Top-rated Chicago side trips

Lake Geneva, WI

Looking for a resort-style getaway just an hour and a half north of Chicago? The town of Lake Geneva in neighboring Wisconsin provides plenty of opportunities for family fun and activity.

Lake Geneva

Located on the shores of Geneva Lake, Lake Geneva used to be a playground for Chicago’s wealthiest residents. It’s now a popular vacation spot, filled with rentals, watersports, and relaxing spots.

Start by wandering along the Geneva Lake Shore Path. Take in the views of the tranquil lake, gaze across in envy at the lakeside mansions, or enjoy the majesty of the boats, bobbing atop the water. Grab a coffee from one of the independent cafes and bakeries in the town and enjoy the calming views.

Next up, it’s time to hit the water! Hire a kayak or jetski and spend a couple of hours zipping around Geneva Lake. Get your adrenaline pumping, and work up an appetite before heading back for a picnic on the beach.

Riviera Beach is one of the closest beaches to the amenities of the town and has a small green space with picnic benches and grills for barbecuing. It’s the perfect spot to wind down in Lake Geneva before heading back to the city.

Starved Rock State Park, IL

Have the urge to get lost in the wilderness? Located just an hour and a half southwest of Chicago is Starved Rock State Park, IL. And it’s an absolute paradise for nature lovers. With free entry and free parking, Starved Rock State Park is the perfect low-cost day trip, allowing you to focus on the beauty all around you.

Starved Rock State Park

Spanning over 2,630 acres, Starved Rock State Park features waterfalls, canyons, trails, and gorgeous woodland. Start by choosing a trail leading to one of the many waterfalls in the state park. As the park is on the Illinois River and is fed by melted glacial water, the waterfalls are in full flow after a rainy night or in the springtime when the glaciers heat up.

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Bring your camera and take a few snaps of the expansive vistas, flowing waterfalls, and deep canyons. Are wild animals more your thing? Keep your binoculars handy as bald eagles, deer, and plenty of migratory birds have been spotted throughout Starved Rock State Park.

Indiana Dunes National Park, IN

Want to spend some much-needed time at the beach? Grab your friends and family, and take the journey just under an hour across the state line to Indiana Dunes National Park, IN. Famous for its soft sands and biodiverse habitat, this park is a beach-bound side trip with a little something extra.

Indiana Dunes National Park, IN

Located on the southern shore of Lake Michigan, Indiana Dunes National Park spans a huge 15,000 acres, featuring 15 miles of beachy coastline. Bring a beach towel and lay out on the golden sands. Take a dip in the refreshing Lake Michigan waters. Learn more about the park’s vital ecosystem at the Paul H. Douglas Center for Environmental Education.

Are you a fan of hitting the trails? Work up a sweat with the park’s more than 50 miles of hiking trails. Whether you’re looking for winding forests, biodiverse wetlands, dusty dunes, or serene rivers, Indiana Dunes National Park delivers. Enjoy a day out in bountiful nature less than an hour away from the hustle and bustle of the Windy City.

Oak Park, IL

Don’t want to drive for miles but still want to get away from the city? Oak Park is a village in the Chicago suburbs, just nine miles away from the city center. What makes Oak Park so special? Not only was it the birthplace of a literary legend, but also features exquisite architecture by an expert in the field.

Oak Park

Jump on the L train and start exploring Oak Park at the Ernest Hemingway Birthplace Museum. The former home of the legendary writer, the Ernest Hemingway Birthplace Museum has been fully restored and reopened. Featuring memorabilia and artifacts from Hemingway’s life, including his childhood, it’s a must-visit for any literary buff.

More into architecture than literature? Just walking around Oak Park, it’s impossible to miss the trademark Prairie School style of Frank Lloyd Wright. Spend the afternoon roaming around the suburbs, noticing the subtle difference in each Frank Lloyd Wright-designed house.

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Take a guided tour of the iconic architect’s house and studio and learn more about how this incredible artist came to design an entire village in Illinois.

Michigan City, IN

Searching for that small-town vibe within easy reach of Chicago? Drive an hour and 20 minutes to the town of Michigan City, IN. Despite its name, the city is definitely in the state of Indiana, named after its perch on the southern shore of Lake Michigan.

Old Lighthouse Museum

This charming lakefront town of Michigan City has plenty to recommend itself, with plenty of tourist attractions to meet the needs of all kinds of visitors.

Start your visit at the Washington Park Zoo, located in the eponymous Washington Park. Stare in awe at the grizzly bears, tigers, alligators, wolves, and more. Learn more about these majestic creatures from the many plaques and knowledgeable guides. Get inspired by the conservation efforts and come away with a new appreciation for this popular tourist destination.

Move on to The Old Lighthouse Museum. Standing proudly on the Lake Michigan shoreline, The Old Lighthouse Museum educates and inspires visitors about local maritime history. Tour the museum, gaze out across the water, and climb up the spiral staircase to the lookout point.

Matthiessen State Park, IL

Want to strap on your hiking boots and visit a park that’s off the beaten path? Two hours away from Chicago, near Oglesby, is Matthiessen State Park, IL. Despite being close to Starved Rock State Park, Matthiessen State Park gets much fewer visitors, making it a small haven for hikers.

Matthiessen State Park

Matthiessen State Park is split into two key areas: Dells Point and Vermilion River. In either, you can enjoy sweating it out across a plethora of hiking trails. Trek towards waterfalls, wander across interesting and geologically significant rock formations or try to spot some native wildlife.

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After a couple of hours of hiking, horseback riding—or even cross-country skiing if you’re in season—finish up at one of the many picnic areas and shelters around Matthiessen State Park. With plenty of restrooms, parking lots, and even accessible hiking routes, this smaller but no less charming state park is a great alternative or add-on to Starved Rock State Park.

Milwaukee, WI

Want to keep that bustling city atmosphere, but want to visit somewhere new? Travel one hour 50 up the coastline of Lake Michigan to Milwaukee, the largest city in Wisconsin.


This thriving metropolis is full of family-friendly attractions and excursions. You could easily spend a few days here. However, if you’ve only got one day in Milwaukee, start it off with a bang at the huge Harley-Davidson Museum. Labeled as a campus, the Harley-Davidson Museum sprawls across 20 acres of waterfront land, complete with a museum, store, and dining options.

Don’t want to eat at the Harley-Davidson Museum? Refuel and set yourself up for the rest of the day at the Milwaukee Public Market in the Historic Third Ward area of Milwaukee. Indulge in delicious fresh seafood and fine local produce, settling into your industrial surroundings. Grab a bite to eat from one of the food vendors, or pick up supplies for a picnic at your next stop.

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With your picnic fodder in hand, wander across to Lakeshore State Park on the banks of Lake Michigan. Kick back on the pebble beach, have a paddle in the cooling waters, or take in the Milwaukee skyline before journeying back to Chicago.

Rockford, IL

Looking for some culture and horticultural excellence? The city of Rockford, IL, lies an hour and 50 minutes northwest of Chicago. The city is home to outstanding gardens, woodlands, and historic sites.

Rockford, IL

Rockford is nicknamed the Forest City. And with good reason. Begin your Rockford side trip at one of the city’s most beloved attractions: the Anderson Japanese Gardens. Covering 12 acres of landscaped gardens, the Anderson Japanese Gardens is an oasis of serenity, tranquility, and culture. Appreciate the plant life and botany on display, or sit and listen to the water features trickle.

Seeking water features with a little more adrenaline attached to them? Soar, splash and swim at Hurricane Harbor, Rockford’s premier water park. Part of the fun-filled Six Flags family, Hurricane Harbor offers a choice of 12 water slides, a wave pool, a lazy river, splash zones, and more!

All this activity got you feeling thirsty? Treat yourself to a local beer at the Prairie Street Brewing Company. With a taphouse that overlooks Rock River, Prairie Street Brewing Company has a wide range of beers designed to impress even the most snobbish beer expert.

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As the brewery also serves food, you can sit out on the deck, eat dinner, and watch the sun dip over the river before returning to the city.

South Bend, IN

Want to visit a local college town with a historic sporting pedigree? Just shy of two hours east, discover South Bend, IN. Home to the University of Notre Dame, South Bend is a must-visit for any college football fans.

South Bend, IN

Start your day out in South Bend at the gorgeous St Joseph River. Want to get the heart rate going? Opt to go tubing on this thriving river, taking in the city all around you as you float and ride atop the water.

Once you’ve dried off, educate yourself at the Studebaker National Museum. Formerly the manufacturer of classic cars, this museum now has plenty of vintage motors on display, complete with the fascinating history of the automotive industry in South Bend. If you’re a petrolhead, you can’t miss the Studebaker National Museum!

Finally, if you’re coming all the way to South Bend, you’re going to want to time it with a big football matchup. Join the legions of fans at the Notre Dame Stadium and cheer on the Notre Dame Fighting Irish football team. As the Fighting Irish are one of the most successful college franchises in the country, the atmosphere here is guaranteed to be electric!

Madison, WI

Looking for a foodie day out and don’t mind a longer drive to get it? Located two hours and 40 minutes northwest of Chicago is Madison, the capital of Wisconsin. In addition to all the history and political significance residing in this city, Madison is also home to an outstanding food and drink scene.

Capitol State Building Madison

Get your day going by strolling down the Capital City State Trail on Madison’s waterfront. Stop and appreciate the awesome convention center, Monona Terrace, designed by Frank Lloyd Wright.

Continue onwards towards the famous Capitol Building, easily recognizable by its giant domed structure. Learn about the way politics works at a state level while enjoying the impressive architecture.

All this walking and history must have worked up an appetite, right? Well, lucky for you, Madison is home to several James Beard award winners. Given to innovative chefs as they’re on the way up to chef superstardom, it’s a huge honor. Winners include Odessa Piper, whose restaurant L’Etoile specializes in farm-to-table cuisine. It was actually one of the first places to do so, thanks to the abundance of Wisconsin’s fresh produce.

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Madison is all about its food & drink scene, with festivals throughout the year, including Craft Beer Week, Great Taste of the Midwest, and the Isthmus Beer & Cheese Festival.

Love cheese curds? (And, let’s be honest: who doesn’t?) The Old Fashioned in Downtown Madison has the best in the whole state. That’s not us saying that: There was an actual vote! (And, yes, they’re that good.)


Ryan O'Rourke is a seasoned traveler and the founder & editor of Treksplorer, a fiercely independent guide to mid-range luxury travel for busy people. With over 20 years of extensive travel experience, Ryan has journeyed through over 50 countries, uncovering hidden gems and sharing firsthand, unsponsored insights on what to see & do and where to eat, drink & stay. Backed by his travel experience and in-depth research, Ryan’s travel advice and writing has been featured in publications like the Huffington Post and Matador Network. You can connect with Ryan on Twitter/X at @rtorourke.

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