The 10 best day trips from Chicago

Chicago all but bursts with fun things to do, from an incredible live-music scene and out-of-this-world dining to priceless cultural treasures and countless neighborhoods that express this city’s one-of-kind character and charm.

Yet it doesn’t take long to find even more to do in the wider region, with parks, historic buildings, sand dunes and even other great cities all within a 2-hour trip of the Loop. If you’re game to explore beyond the city limits, here are 10 fantastic day trips from Chicago.

1. Explore the terrific college town of Evanston

Travel time: 40 minutes
How to travel: By “L” (metro)

Chicago’s neighbor to the immediate north, Evanston is a lakefront town of sprawling old houses, artisan shops, bookish cafes and (of course) the sprawling campus of Northwestern University. After you’ve strolled NU’s stately quads, check out the quirky American Toby Jug Museum, which has the world’s largest collection of character-shaped jugs (think Barack Obama, Mick Jagger and R2-D2 as ceramic pitchers); and the Baha’i House of Worship, a grandiose temple surrounded by peaceful gardens.

Both are free – which leaves money in your pocket to rent a sailboat, kayak or stand-up paddleboard at the Northwestern University Sailing Center and get out on glimmering Lake Michigan. Back on land, you can have a wander among the boutiques, brewpubs and brioche-laden bakeries (Hewn is a favorite) that abound in the walkable downtown.

How to get to Evanston from Chicago: Chicago’s “L” trains serve Evanston. During weekday peak times, take the Purple Line direct from downtown Chicago, or the Red Line to Howard station then switch to the Purple Line. It’s about a 40-minute trip, with departures every 10 minutes or so.

2. See some of Frank Lloyd Wright’s most important work in Oak Park

Travel time: 45 minutes
How to travel: By “L” (metro)

For 20 years, master architect Frank Lloyd Wright lived in the leafy suburb of Oak Park, next door to Chicago. Today, fans come from all over the world to tour his home and studio (1889), where he developed his famous Prairie style. Nearby Unity Temple (1905–08) is a seminal building in the development of modern architecture, and was named to UNESCO World Heritage List in 2019.

Born in a sprawling Victorian home just a few blocks from Wright’s pad, Ernest Hemingway is Oak Park’s other famous son. The site is now maintained as the Hemingway Birthplace Museum and gives a peek at Papa’s formative years.

How to get to Oak Park from Chicago: It’s a simple excursion via Chicago’s L. Take the Green Line train from the Loop to Oak Park station; the town’s attractions are all within a mile’s walk.

3. Visit iconic film locations on the North Shore

Travel time: 1 hour
How to travel: By Metra (commuter rail)

It’s easy to see why the filmmakers behind the Christmas classic Home Alone were drawn to the suburb of Winnetka, with its tidy streets and vibe of low-key affluence. Even though 671 Lincoln is a private residence, you can stop by for a quick photo of the home of the McCallister family – so bravely defended from burglars by Kevin. Other filmmakers have been inspired by the North Shore, too – especially John Hughes, who filmed much of Ferris Bueller’s Day Off and Sixteen Candles in Winnetka and nearby Glencoe and Highland Park.

The area also offers plenty of natural beauty to explore. Take a wander through the 385-acre Chicago Botanic Garden near Glencoe to enjoy the scenic walking and biking trails, wildlife viewing opportunities, thought-provoking exhibitions and innovative workshops. Skokie Lagoons offers a year-round retreat for nature enthusiasts, with activities such as hiking, boating and cross-country skiing.

How to get to the North Shore from Chicago: From Chicago’s Ogilvie Transportation Center, take the UP-N Metra line to Winnetka or Glencoe.

4. Spot prairie bison near historic Joliet

Travel time: 1 hour 20 minutes
How to travel: By train or by car

Joliet is a haven for history buffs. Head to the Illinois Rock & Roll Museum to learn all about acclaimed icons of the music industry, tour the magnificent Rialto Square Theater or brave the halls of the Old Joliet Prison. Take a break from all the sightseeing and grab a bite to eat at Joe’s Hot Dogs, a local favorite that’s been serving up classics since 1953.

After spending some time in town, make your way about 20 minutes south to Midewin National Tallgrass Prairie. Once part of the Joliet Army Ammunition Plant, the landscape has since been restored into a natural prairie habitat. The protected lands are home to 18 endangered or threatened species, including a small herd of bison. Bring your binoculars and head to the welcome center or Iron Bridge Trailhead to scan the pastures for bison on a self-guided tour.

How to get to Joliet from Chicago: Amtrak operates an hour-long train to Joliet, with two daily morning departures from Chicago Union Station. Alternatively, you can drive just over an hour along I-55 or I-57 before joining I-80 into Joliet. 

5. Admire Harleys and artwork in Milwaukee

Travel time: 1 hour 30 minutes
How to travel: By train or by car

Ninety miles up the Lake Michigan shoreline, Milwaukee makes for a rollicking (if ambitious) day trip from Chicago. With the arguable exception of Miller Brewing Company, Harley-Davidson is the city’s most famous brand: stop by the Harley-Davidson Museum to gawk at hundreds of motorcycles, including Elvis’ custom-built hog. Nestled in a lakefront park, the Milwaukee Art Museum has a kinetic, Santiago Calatrava–designed exterior “wing” that soars open and shut, dazzling visitors. Inside, the collection of outsider art and Georgia O’Keeffe paintings also impress.

During baseball season, American Family Field is the place to be for beers, bratwursts and the oddball sixth-inning foot race between people dressed in giant sausage costumes. Milwaukee has a reputation as a drinker’s paradise, with more bars per capita than anywhere in the US save New Orleans. Friendly neighborhood taverns pop up on almost every corner; Champion’s might be the best example of the local spirit.

How to get to Milwaukee from Chicago: Amtrak runs seven trains daily to downtown Milwaukee, with a journey time of 90 minutes. By car, take I-94 for the roughly 2-hour trip.

6. Get into nature at Indiana Dunes National Park

Travel time: 1 hour and 30 minutes
How to travel: By train or by car

Rustling grasses, bird-filled marshes and white-pine forests fill a whopping stretch of Lake Michigan shoreline at Indiana Dunes National Park, which feels a world away from the big city. Here, rugged beaches beckon, while hiking trails meander up the sand and through the woodlands.

Try the 3 Dune Challenge, a view-tastic 1.5-mile climb to the park’s highest dunes: Mt Jackson, Mt Holden and Mt Tom. (Just to confuse you, they all lie within Indiana Dunes State Park, fully within the borders of the national park.) Biking, paddling and winter snowshoeing are other fun activities available in this natural treasure.

How to get to the Indiana Dunes from Chicago: South Shore Line commuter trains make the 70-minute trip several times daily from downtown Chicago to Dune Park station. By car, the 50-mile trip takes 1 to 2 hours, depending on traffic.

7. Tour the lakeside hamlets of Harbor Country

Travel time: 1 hour 30 minutes
How to travel: By car

An easy drive across the top of Indiana and just over the border into Michigan, Harbor Country comprises several lakeside hamlets where Chicagoans retreat for a taste of small-town life. In popular New Buffalo, you can catch a wave at the public beach and follow it up with suds at the Beer Church.

Three Oaks is a bohemian farm-and-arts village; be sure to browse the galleries and design shops along Elm St. Antique stores and folksy delis abound in Union Pier, Lakeside, Harbert and Sawyer. Warren Dunes State Park near Sawyer offers outdoor adventures along its 6 miles of hiking trails. Several wineries in the area, such as Tabor Hill, offer tastings.

How to get to Harbor Country from Chicago: Harbor Country is a 90-minute drive east from downtown Chicago via I-90 and I-94. While Amtrak stops in New Buffalo, train times aren’t convenient for day trips, and you’ll need your own wheels to access the other towns.

8. Walk a section of the 21-mile Geneva Lake Shore Path

Travel time: 1 hour 30 minutes
How to travel: By car

Old-money Chicagoans fled to Geneva Lake, Wisconsin, in the late 1800s to escape the urban heat and relax in the pristine, spring-fed water. It’s still high on the getaway list, and while the mansion-strewn shoreline is sometimes called “the Hamptons of the Midwest,” visitors of more modest means are most welcome.

Nowhere is this more evident than on the Lake Shore Path, the 21-mile public trail that goes through all water’s-edge properties – like, through their front lawns! – affording close-up views of the mega estates. Taking a boat ride with Lake Geneva Cruise Line is a must, as is a trip to the old-school Cheese Box for hunks of aged cheddar, havarti and other Wisconsin-made goodness.

How to get to Geneva Lake from Chicago: You need a car for this day trip. Lake Geneva, the main town on Geneva Lake, is 80 miles northwest of Chicago. Take I-94 north to Wisconsin highway 50 west. The trip takes 90 minutes to 2 hours by car.

9. Savor nature in Rockford, the “City of Gardens”

Travel time: 1 hour 40 minutes
How to travel: By car

Once nicknamed the “Forest City” thanks to its verdant neighborhoods, Rockford combines history, culture and art with numerous natural attractions. More recently known as the “City of Gardens,” Rockford’s jewel is the impossibly beautiful Anderson Japanese Gardens. Designed by Hoichi Kurisu, the gardens are a masterful arrangement of stone, water and plants, inspiring tranquility in all who meander the beautifully curated landscapes.

Just south of downtown Rockford, the Klehm Arboretum & Botanic Garden features themed specialty gardens, a children’s garden and easy walking trails. For a more rustic nature experience, Rock Cut State Park offers year-round outdoor activities 20 minutes northeast of the city. Other attractions worth checking out include the Rock Men and gardens in Sinnissippi Park – as well as a different kind of park, Beyer Stadium, former home of the Rockford Peaches (the inspiration for the team in A League of Their Own).

How to get to Rockford from Chicago: The fastest route is by car via I-290 W and then I-90 W. 

10. Discover outdoor adventures in La Salle County

Travel time: 2 hours
How to travel: By car

In LaSalle County, just under 2 hours from downtown Chicago, a trio of beautiful state parks serves up stunning rock formations, cascading waterfalls and spectacular overlooks. Starved Rock State Park, Matthiessen State Park and Buffalo Rock State Park each has its own unique features and attractions.

Known for its trails and canyons, Starved Rock is the most popular of the bunch. Mattheissen offers a diverse range of activities, from archery and equestrian trails to mountain biking and cross-country skiing. A pair of bison can be seen grazing in Buffalo Rock, along with sweeping views of the Illinois River from two observation decks along the River Bluff Trail.

If you don’t want to spend the entire day in the woods, check out the nearby towns of Utica, La Salle, Ottawa or Oglesby for mom-and-pop restaurants, niche museums and plenty of small-town appeal.

How to get to La Salle County from Chicago: Visiting the state parks is easiest by car, via I-80 W.