17 top day trips from Chicago

Chicago boasts impressive skyscrapers, lively music venues, and renowned museums that can keep you busy for weeks. However, just outside the city, you can also hike up sand dunes at a national park, ride a Harley, and explore local wineries.

Here are 17 convenient day trips, all within three hours of Chicago.

1.5 hours away or less:

1. Visit the insightful Illinois Holocaust Museum

Travel time: 25 minutes

The Illinois Holocaust Museum ranks as the third-largest Holocaust Museum globally, following those in Jerusalem and Washington, DC. In addition to its poignant Nazi-era rail car and survivor video testimonies from WWII, the museum features thought-provoking art addressing genocides in Armenia, Rwanda, Cambodia, and more. The special exhibitions are particularly noteworthy.

Getting to the Illinois Holocaust Museum from Chicago: By car, take I-94 – the 18-mile drive takes around 25 minutes. For public transport, take the Union Pacific North (UP-N) train from Ogilvie Transportation Center to Davis Street/Evanston. Then, catch the 208 bus at the Davis and Maple stop and get off at Golf Rd and Woods Dr. The museum is a short two-minute walk from there. The entire trip takes just over an hour.

2. Discover Evanston, one of the premier college towns in the US

Travel time: 40 minutes

Evanston lies just north of Chicago, a charming lakeside town filled with historic homes, artisan boutiques, and cozy cafes where college students fuel up on coffee. Be sure to visit the quirky American Toby Jug Museum, boasting the largest collection of character-shaped jugs in the world (think ceramic pitchers shaped like Barack Obama, Mick Jagger, and R2-D2), as well as the stunning Baha’i House of Worship, a beautiful temple nestled in serene gardens.

Both attractions are free, allowing you to save some cash for renting a sailboat, kayak, or stand-up paddleboard at the Northwestern University Sailing Center to enjoy the sparkling waters of Lake Michigan. Alternatively, explore the walkable downtown filled with unique shops, brewpubs, and delightful bakeries like Hewn.

How to reach Evanston from Chicago: Chicago's L trains provide service to Evanston. During peak weekday hours, take the Purple Line directly from downtown Chicago or ride the Red Line to Howard station and transfer to the Purple Line. The journey takes about 40 minutes, with trains departing approximately every 10 minutes.

3. Support local businesses in Andersonville

Travel time: 25 minutes

Nestled on Chicago's north side, the vibrant neighborhood of Andersonville is celebrated for its Swedish heritage and artistic spirit. This charming urban area features a diverse culinary landscape and a fascinating array of independent shops. 

Explore the neighborhood’s Swedish roots at the Swedish American Museum or check out the ever-changing vendors at Andersonville Galleria, offering everything from home decor to pet supplies, jewelry, and clothing. For those curious about the quirky side of Andersonville, the eclectic collections at Wooly Mammoth and the enchanting Chicago Magic Lounge are must-sees. As one of Chicago's largest LGBTQ+ communities, Pride in Andersonville combines Swedish culture for a unique twist on the annual summer festivities. 

How to reach Andersonville from Chicago: If you're driving, take 41 north for a picturesque ride along the Lake Michigan coastline. For public transport, catch the Red Line of Chicago’s L train to Bryn Mawr station. Alternatively, you can take the 147 Bus heading toward Howard, which stops at Sheridan & Berwyn.

4. Explore the hub of modernist architecture in Oak Park

Travel time: 45 minutes

Architect Frank Lloyd Wright resided in the lush suburb of Oak Park, just next to Chicago, for two decades. Enthusiasts from around the globe visit his home and studio, where he pioneered the iconic Prairie style, and admire his Unity Temple—designated a UNESCO World Heritage site in 2019, it is regarded as the first modern-style building.

Another notable figure from Oak Park is Ernest Hemingway. He was born in a grand Victorian house just a few blocks away from Wright's residence, which now operates as the Hemingway Birthplace Museum, offering insights into the early life of the famous author.

How to travel to Oak Park from Chicago: It’s an easy trip via Chicago’s public transit system. Simply take the Green Line L train from downtown to Oak Park station, from where everything is within a mile's walk.

5. Explore famous film sites in the North Shore neighborhoods

Travel time: 1 hour

It’s no wonder the filmmakers of the holiday classic Home Alone selected the Winnetka suburbs for the McCallister family home. While the house at 671 Lincoln is privately owned, you can still stop by for a quick photo op. Winnetka isn’t the only North Shore area featured in notable films; movie enthusiasts can also spot locations from other John Hughes classics like Ferris Bueller’s Day Off and Sixteen Candles across Winnetka and nearby Glencoe. 

The region also boasts plenty of natural attractions to discover. The expansive 385-acre Chicago Botanic Garden near Glencoe is a must-see, offering beautiful walking and biking paths, wildlife viewing, engaging exhibitions, and creative workshops. Skokie Lagoons serves as a year-round haven for nature lovers, featuring activities like hiking, boating, and cross-country skiing.

How to reach the North Shore neighborhoods from Chicago: Take the UP-N train to Winnetka or Glencoe. If you’re heading to Skokie, you can take I-94. 

6. Observe prairie bison near historic Joliet

Travel time: 1 hour 20 minutes

Joliet is a treasure trove for history enthusiasts. While you’re there, explore the Illinois Rock & Roll Museum, tour the stunning Rialto Square Theater, or venture into the Old Joliet Prison. For a taste of history, visit Joe’s Hot Dogs, a local institution serving classic fare since 1953. 

After exploring the town, head about 20 minutes south to Midewin National Tallgrass Prairie. Once part of the Joliet Army Ammunition Plant, this area has been transformed into a natural prairie habitat. This protected landscape is home to 18 endangered or threatened species, including a small herd of bison. Bring your binoculars and visit the Welcome Center or Iron Bridge Trailhead for guided or self-guided tours to spot bison in their pastures.

How to reach Joliet from Chicago: If you’re driving, it takes just over an hour via I-55 or I-57 to I-80 into Joliet. Amtrak also offers train service to Joliet, with two daily morning departures from Chicago Union Station, making for an hour-long trip.

7. Immerse yourself in nature at Indiana Dunes National Park

Travel time: 1 hour, 30 minutes

The Indiana Dunes National Park features rustling grasses, bird-filled marshes, and white-pine forests along a vast stretch of Lake Michigan's shoreline, making it feel miles away from the city. Explore rugged beaches and charming hiking trails that wind through the sand and woodlands.

Take on the 3 Dune Challenge, a scenic 1.5-mile trek to the park’s highest dunes: Mt. Jackson, Mt. Holden, and Mt. Tom (which, to add some confusion, are located in Indiana Dunes State Park, a section of the national park). The park also offers biking, paddling, and winter snowshoeing for outdoor enthusiasts.

How to reach Indiana Dunes National Lakeshore from Chicago: The South Shore Line commuter trains run several times daily, making the 80-minute journey from downtown Chicago to Dune Park station. If you're driving, the 50-mile trip typically takes one to two hours, depending on traffic conditions.

8. Discover Harleys and art in Milwaukee

Travel time: 1 hour, 30 minutes

Milwaukee, the largest city in Wisconsin, offers an exciting day trip from Chicago. Visit the Harley-Davidson Museum to marvel at hundreds of motorcycles, including Elvis’s custom hog. Milwaukee is the birthplace of Harleys, so it's no surprise that the city has a deep appreciation for these iconic bikes. The Milwaukee Art Museum impresses with its stunning kinetic “wing” that opens and closes, along with its collection of outsider art and Georgia O’Keeffe masterpieces.

During baseball season, Miller Park is the go-to spot for enjoying beers, bratwursts, and the quirky sixth-inning sausage race featuring people in giant sausage costumes. Milwaukee is renowned as a drinker’s paradise, boasting more bars per capita than any other U.S. city except New Orleans. You'll find friendly neighborhood taverns on nearly every corner, with Champion’s embodying the local spirit.

How to get to Milwaukee from Chicago: Amtrak operates seven daily trains to downtown Milwaukee, taking about 90 minutes. If you prefer driving, follow I-94 for a roughly two-hour journey.

9. Explore the lakeside villages of Harbor Country

Travel time: 1 hour, 30 minutes

Harbor Country features a collection of lakeside villages just beyond the Michigan border, where Chicagoans escape for a slice of small-town charm. New Buffalo stands out as the most resort-like spot, perfect for catching waves at the public beach followed by a drink at the Beer Church.

Three Oaks is a quirky village known for its farm and arts scene, offering galleries and design shops along Elm Street. In Union Pier, Lakeside, Harbert, and Sawyer, you’ll find antique shops and quaint delis. For outdoor enthusiasts, Warren Dunes State Park near Sawyer has 6 miles of hiking trails. Nearby wineries, including Tabor Hill, provide delightful tasting experiences.

How to reach Harbor Country from Chicago: It’s a 90-minute drive east from downtown Chicago via I-90 and I-94. While Amtrak services New Buffalo, the schedule may not be ideal for day trips, so having your own transportation is recommended to explore the other towns.

10. Stroll along a section of the 21-mile Geneva Lake Shore Path

Travel time: 1 hour, 30 minutes

In the late 1800s, affluent Chicagoans flocked to Geneva Lake to escape the city heat and enjoy its crystal-clear, spring-fed waters. It remains a popular retreat, and while the shoreline is sometimes referred to as “the Hamptons of the Midwest,” visitors from all walks of life are warmly welcomed.

This inclusivity is particularly clear on the Lake Shore Path, a 21-mile public trail that winds through the properties along the water’s edge—often right past their front lawns! Don’t miss a boat tour with the Lake Geneva Cruise Line, and be sure to stop by the classic Cheese Box for delicious aged cheddar, havarti, and other Wisconsin delights.

How to reach Geneva Lake from Chicago: A car is necessary for this day trip. Lake Geneva, the primary town on Geneva Lake, is located 80 miles northwest of Chicago. Simply take I-94 north to Wisconsin Highway 50 west. The drive typically takes between 90 minutes and two hours.

11. Discover family-friendly adventures in Naperville

Travel time: 1 hour, 30 minutes

The lively western suburb of Naperville perfectly blends small-town charm with a vibrant urban feel. In addition to popular attractions like escape rooms, arcades, and movie theaters, Naperville is home to the DuPage Children’s Museum, where kids can engage with interactive, educational exhibits designed to ignite their curiosity. The Morton Arboretum invites visitors to connect with nature through its stunning gardens, and the playful Children’s Garden is perfect for energetic kids who love to climb, splash, and dig.

No trip to Naperville is complete without a walk along the Naperville Riverwalk. This 1.75-mile path follows the DuPage River, weaving through downtown attractions, parks, fountains, playgrounds, and the delightful Centennial Beach. Please note: the beach operates seasonally and charges an admission fee of $14-16 per day for non-residents.

How to reach Naperville from Chicago: If you prefer public transit, take the Burlington Northern Santa Fe (BNSF) train to Naperville station, which is just a 5-minute walk from the Children’s Museum and 15 minutes from downtown. If driving, head south on I-55.

2 to 3 hours away

12. Experience outdoor adventures in La Salle County

Travel time: 2 hours

Located less than two hours from downtown Chicago, La Salle County boasts three stunning state parks featuring impressive rock formations, cascading waterfalls, and breathtaking overlooks. These parks include Starved Rock State Park, Matthiessen State Park, and Buffalo Rock State Park, each offering unique attractions and experiences.

Starved Rock, famous for its scenic trails and canyons, is the most frequented of the state parks. Matthiessen offers a variety of activities, including archery, horseback riding, mountain biking, and cross-country skiing. At Buffalo Rock, you can spot a pair of bison grazing and enjoy expansive views of the Illinois River from two observation decks along the River Bluff Trail. If you prefer a break from nature, nearby towns like Utica, La Salle, Ottawa, or Oglesby offer charming mom-and-pop restaurants, unique museums, and a delightful small-town atmosphere.

How to reach La Salle County from Chicago: The easiest way to visit the state parks is by car via I-80 W.

13. Discover the “City of Gardens” in Rockford

Travel time: 2 hours

Once known as “the Forest City” for its lush neighborhoods, Rockford combines history, culture, and art amid its many natural attractions. Its new title, the “city of gardens,” shines through in the serene Anderson Japanese Gardens. Designed by Hoichi Kurisu, these gardens beautifully blend stone, water, and plants, creating a peaceful retreat for visitors to enjoy as they wander through the meticulously designed landscape.

Just south of downtown Rockford, the Klehm Arboretum & Botanic Garden boasts themed gardens, a dedicated children’s garden, and accessible walking trails. For those seeking a more rugged outdoor experience, Rock Cut State Park offers year-round activities just 20 minutes northeast of the city. Additional attractions include the Rock Men and the gardens within Sinnissippi Park, as well as Beyer Stadium, the historic home of the Rockford Peaches.

How to travel to Rockford from Chicago: The quickest route is by car via I-90. Amtrak services operate hourly from Union Station to Rockford.

14. Embrace school spirit in South Bend, Indiana

Travel time: 2 hours

Just north of South Bend, the Fighting Irish of Notre Dame attract crowds to their picturesque campus. Founded in 1842, the university is steeped in history and tradition. Beyond the vibrant game day atmosphere, visitors can explore iconic landmarks like the gleaming Golden Dome of the main building, the impressive Word of Life Mural (affectionately known as Touchdown Jesus), and the serene Grotto of Our Lady of Lourdes.

In addition to exploring the campus, South Bend boasts a variety of free activities. Both the Raclin Murphy Museum of Art and the South Bend Museum of Art welcome visitors at no charge. As night falls, the South Bend River Lights create a dazzling display downtown. While you're there, stop by Revenant Coffee Bar inside the Dainty Maid Food Hall for a distinctive brew, then enjoy the Irish ambiance at Fiddler’s Hearth, where you can savor classic pub dishes, enjoy a pint (or two), and catch some live music.

Getting to South Bend from Chicago: A scenic drive along I-90 will take you to South Bend in just under 2 hours. Alternatively, the South Shore Line connects downtown Chicago to the South Bend Regional Airport, and Amtrak services run from Union Station to the west side of South Bend.

15. Embrace the simple life in Shipshewana, Indiana

Travel time: 2 hours, 30 minutes

Situated in the heart of Indiana’s Amish Country, Shipshewana serves as a central hub for LaGrange County’s Amish community, where shopping and socializing abound. Discover Amish-Mennonite history and traditions at the Menno-Hof Museum, then dive into the local culture with a traditional buggy ride, visits to nearby farms, and the chance to admire the craftsmanship of local artisans.

Pick up the self-guided Off the Beaten Path tour map at the Shipshewana Visitor’s Center to explore colorful barn quilts and charming small businesses across LaGrange County. If you prefer a one-stop shopping experience, visit the Midwest’s largest flea market in Shipshewana, where hundreds of vendors showcase their goods every Tuesday and Wednesday from May to September. Come with an appetite to enjoy traditional Amish dishes and freshly baked treats.

Getting to Shipshewana from Chicago: Take I-90 E. Greyhound also provides service to Shipshewana through Barons Bus, with a travel time of just over 3 hours.

3 hours away or more

16. Experience Dutch culture in Holland, Michigan

Travel time: 3 hours

Nestled along the shores of Lake Macatawa in Michigan, the enchanting town of Holland invites visitors to experience Old World charm with its vibrant tulips, spinning windmills, and traditional Dutch architecture. Enjoy a leisurely bike ride along paved paths or wander the cobblestone streets of downtown, where a variety of local shops and dining options await.

Dive into Dutch heritage by touring the DeZwaan Windmill or visiting the Holland Museum. Nelis’ Dutch Village offers an interactive experience celebrating the Netherlands' rich traditions. If you happen to visit in May, the Veldheer Tulip Gardens showcase stunning fields of colorful blooms. The iconic Big Red Lighthouse provides breathtaking views from the north pier at Holland State Park.

Getting to Holland from Chicago: Amtrak’s Pere Marquette line connects Union Station to Holland in 3 hours. By car, the journey takes just under 3 hours via I-90 E to I-196 N.

17. Discover Madison, Wisconsin for a day (or more)

Travel time: 3 hours

With so much to explore in Madison, you might find yourself extending your day trip into a weekend escape. The city is rich in art, history, culture, entertainment, and natural beauty. Nestled between Lake Monona and Lake Mendota, Downtown Madison features highlights like the Wisconsin State Capitol, the free Chazen Museum of Art, the Madison Children’s Museum, and the Allen Centennial Garden.

Food lovers will revel in Madison's diverse culinary scene, offering everything from Asian-inspired dishes at Ahan to farm-fresh options at Mint Mark. Just a short distance from downtown, the Olbrich Botanical Gardens hosts live music, interactive exhibits, and educational events set amidst specialty gardens influenced by seasonal and international themes.

If you’re planning a weekend in Madison, consider a short drive north to visit Devil’s Lake State Park and the Wisconsin Dells. At Devil’s Lake, you can hike 30 miles of trails with stunning views from quartzite bluffs, while Wisconsin Dells offers year-round family fun with water parks, ski resorts, scenic tours, and live theater.

Getting to Madison from Chicago: Amtrak provides an hourly bus service that takes 3 hours and 35 minutes from Union Station to Madison. By car, the drive is just under 3 hours via I-90 W.