The 17 best day trips from Chicago

Chicago has enough cloud-poking towers, rockin’ live-music clubs and world-class museums to keep you occupied for weeks. But just beyond city limits, you can also scale sand dunes at a national park, rev a Harley and amble around wineries.

Here are 17 easy day trips that are no more than three hours away from Chicago.

1.5 hours away or less:

1. Encounter the thought-provoking Illinois Holocaust Museum

Travel time: 25 minutes

The Illinois Holocaust Museum is the third-largest Holocaust Museum in the world, after those in Jerusalem and Washington, DC. Besides its haunting Nazi-era rail car and videos of survivors' stories from WWII, the venue contains thought-provoking art about genocides in Armenia, Rwanda, Cambodia and other countries. The special exhibitions are particularly impressive.

How to get to the Illinois Holocaust Museum from Chicago: By car, take I-94 – the 18-mile trip takes about 25 minutes. On public transportation, take the Union Pacific North (UP-N) train at Ogilvie Transportation Center to Davis Street/Evanston. Catch the 208 bus at the Davis and Maple stop and get off at Golf Rd and Woods Dr. It's a two-minute walk to the museum. The trip takes a little over an hour.

2. Explore Evanston, one of the top college towns in the US

Travel time: 40 minutes

Evanston is Chicago’s neighbor to the north, a lakefront town of sprawling old houses, artisan shops and bookish cafes where college students caffeinate. Check out the quirky American Toby Jug Museum, with 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, an eye-popping 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. Otherwise, wander among the boutiques, brewpubs and brioche-laden bakeries like Hewn that pepper the walkable downtown.

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

3. Shop local in Andersonville

Travel time: 25 minutes

On the north side of Chicago lies the eclectic neighborhood of Andersonville. Known for its Swedish heritage and artistic flair, the charming urban neighborhood has a diverse food scene and an intriguing collection of independently-owned shops.

Discover the area’s Swedish roots at the Swedish American Museum or browse the rotating vendors at Andersonville Galleria selling everything from home goods and pet gear to jewelry and apparel. Those interested in the more eccentric side of Andersonville shouldn’t miss the curious collection at Wooly Mammoth and the mesmerizing Chicago Magic Lounge. As the home of one of Chicago’s largest LGBTQ+ communities, Pride in Andersonville integrates Swedish culture for a one-of-a-kind twist on the annual summer celebration.

How to get to Andersonville from Chicago: If traveling by car, take 41 north for a scenic jaunt up the Lake Michigan coast. Using public transit, take Chicago’s L train on the Red Line to Bryn Mawr station. Another option is the 147 Bus toward Howard stopping at Sheridan & Berwyn.

4. See the home of modernist architecture in Oak Park

Travel time: 45 minutes

Architect Frank Lloyd Wright lived in the leafy suburb of Oak Park, next door to Chicago, for 20 years. Fans come from all over the world to tour his home and studio where he developed the famous Prairie style, as well as to gawp at his Unity Temple – named a UNESCO World Heritage site in 2019 – that’s considered to be the first modern-style building.

Ernest Hemingway is Oak Park’s other famous son. He was born in a sprawling Victorian home just a few blocks from Wright’s pad. It’s 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 public transit system. Take the Green Line L train from downtown to Oak Park station, from which everything is within a mile's walk.

5. Visit iconic film locations in the North Shore neighborhoods

Travel time: 1 hour

It’s easy to see why the filmmakers behind the Christmas classic Home Alone chose the suburbs of Winnetka for the McCallisters’ residence. Even though the house at 671 Lincoln is a private address, you can stop by for a quick photo. Home Alone wasn’t the only major film to feature areas around the North Shore either. Movie buffs can spot locations across Winnetka and neighboring Glencoe in other iconic films from the legendary John Hughes, including Ferris Bueller’s Day Off and Sixteen Candles.

The area also offers plenty of natural wonders to explore. The sprawling 385-acre Chicago Botanic Garden is a must-visit near Glencoe with 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 from hiking and boating to cross-country skiing.

How to get to the North Shore neighborhoods from Chicago: Take the UP-N to Winnetka or Glencoe from Chicago. If heading out to Skokie take the 1-94.

6. Spot prairie bison near historic Joliet

Travel time: 1 hour 20 minutes

Joliet is a haven for history buffs. While in town, you can learn about acclaimed musicians at the Illinois Rock & Roll Museum, tour the magnificent Rialto Square Theater or brave the halls of the Old Joliet Prison. For a historic bite, head to 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 guided or self-guided tour.

How to get to Joliet from Chicago: By car, travel just over an hour along I-55 or I-57 to I-80 into the city. Amtrak operates a train to Joliet with two daily morning departures from Chicago Union Station for an hour-long trip.

7. Get into nature at Indiana Dunes National Park

Travel time: 1 hour, 30 minutes

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. Rugged beaches beckon, and sweet 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, these are in Indiana Dunes State Park, a pocket within the national park.) Biking, paddling and winter snowshoeing are other fun activities available in the park.

How to get to the Indiana Dunes National Lakeshore from Chicago: South Shore Line commuter trains make the 80-minute trip several times daily from downtown Chicago to Dune Park station. By car, the 50-mile trip takes one to two hours, depending on traffic.

8. Admire Harleys and artwork in Milwaukee

Travel time: 1 hour, 30 minutes

Milwaukee is Wisconsin's largest city, and it's a rollicking day trip from Chicago. Stop by the Harley-Davidson Museum to gawk at hundreds of motorcycles, including Elvis’s custom-built hog. Harleys were invented in Milwaukee, hence the big bike love. The Milwaukee Art Museum drops jaws with its kinetic “wing” that soars open and shut, as well as its outsider art and Georgia O’Keeffe paintings.

During baseball season, Miller Park 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 besides New Orleans. Friendly neighborhood taverns pop up on almost every corner. Champion’s shows 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 the I-94 for the roughly two-hour trip.

9. Tour the lakeside hamlets of Harbor Country

Travel time: 1 hour, 30 minutes

Harbor Country comprises several lakeside hamlets just over the Michigan border, where Chicagoans retreat for a taste of small town life. New Buffalo is the most resort-y of the bunch, where 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 where you can browse Elm Street’s galleries and design shops. Antique stores and folksy delis abound in Union Pier, Lakeside, Harbert and Sawyer. Warren Dunes State Park near Sawyer offers outdoor adventures along 6 miles of hiking trails. Several wineries, such as Tabor Hill, surround the communities and 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, the times aren’t convenient for day trips, and you’ll need your own wheels to access the other towns.

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

Travel time: 1 hour, 30 minutes

Old-money Chicagoans fled to Geneva Lake in the late 1800s to escape the urban heat and chill in the true-blue, 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 just as 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 – right through their front lawns! – for 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 two hours by car.

11. Enjoy family-friendly fun in Naperville

Travel time: 1 hour, 30 minutes

The vibrant western suburb of Naperville toes the line between small town charm and bustling urban center. Beyond crowd-pleasing attractions like escape rooms, arcades and movie theaters, Naperville is home to the DuPage Children’s Museum where kids can explore educational, interactive exhibits to spark their curiosity and imagination. The Morton Arboretum connects visitors with nature as they wander the diverse gardens. The whimsical Children’s Garden is ideal for energetic kids who love to climb, splash and dig.

A visit to Naperville isn’t complete without a stroll along the Naperville Riverwalk. Following the DuPage River, this 1.75 mile path weaves among downtown hot spots, parks, fountains, playgrounds and the watery wonderland of Centennial Beach. Note: the beach is open seasonally and requires an admission fee ranging from $14-16 per day for non-residents.

How to get to Naperville from Chicago: Via public transit, take the Burlington Northern Santa Fe (BNSF) train to Naperville station (just 5 minutes walk to the Children’s Museum and 15 minutes from downtown). By car, take I-55 S.

2 to 3 hours away

12. Discover outdoor adventures in La Salle County

Travel time: 2 hours

Just under two hours from downtown Chicago, three beautiful state parks await with stunning rock formations, cascading waterfalls and spectacular overlooks. Nestled in La Salle County, you’ll find Starved Rock State Park, Matthiessen State Park and Buffalo Rock State Park each with 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, taking 1-80 W.

13. Experience the “City of Gardens” in Rockford

Travel time: 2 hours

Once nicknamed “the Forest City” for its verdant neighborhoods, Rockford blends history, culture and art among its numerous natural attractions. Its new moniker, the “city of gardens,” is best exemplified by the transportive 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 landscape.

The Klehm Arboretum & Botanic Garden just south of downtown Rockford 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 just 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.

How to get to Rockford from Chicago: The fastest route is by car via 1-90. Amtrak service runs hourly from Union Station to Rockford.

14. Show some school spirit in South Bend, Indiana

Travel time: 2 hours

Just north of South Bend, the Fighting Irish of Notre Dame draw thousands to the scenic university campus. Established in 1842, the school is rich in history and tradition. In addition to the raucous atmosphere of game day, the University of Notre Dame is home to must-visit landmarks from the shining Golden Dome of the main building to the towering Word of Life Mural (also known as Touchdown Jesus) and the Grotto of Our Lady of Lourdes.

Along with touring the campus, South Bend offers tons of free things to do. The Raclin Murphy Museum of Art on Notre Dame’s campus and the South Bend Museum of Art are free to visit, and when the sun goes down, the South Bend River Lights are a must-see spectacle downtown. While downtown, grab a unique brew at Revenant Coffee Bar located inside the Dainty Maid Food Hall, then keep the Irish spirit alive at Fiddler’s Hearth with classic pub fare, a cold pint (or two) and live music.

How to get to South Bend from Chicago: A road trip by car will get you to South Bend from Chicago in just under 2 hours along I-90. The South Shore line runs from downtown Chicago to the South Bend Regional Airport. Amtrak runs from Union Station to the west side of South Bend.

15. Savor the simple life in Shipshewana, Indiana

Travel time: 2 hours, 30 minutes

The heart of Indiana’s Amish Country, Shipshewana is the hub for LaGrange County’s Amish community to shop and socialize. Learn about Amish-Mennonite history and beliefs at the Menno-Hof Museum, then immerse yourself in the town’s culture while taking a traditional buggy ride, visiting nearby farms and admiring the craftsmanship of local artisans.

The self-guided Off the Beaten Path tour map can be picked up at the Shipshewana Visitor’s Center and showcases colorful barn quilts and small businesses around LaGrange County. If you’d rather do your shopping all in one place, the Midwest’s largest flea market is in Shipshewana with hundreds of vendors hawking their wares on Tuesdays and Wednesdays from May to September. Be sure to come hungry so you can sample traditional Amish cuisine and handcrafted baked goods.

How to get to Shipshewana from Chicago: Take I-90 E. Greyhound also offers service to Shipshewana via Barons Bus. The bus takes just over 3 hours.

3 hours away or more

16. Celebrate Dutch culture in Holland, Michigan

Travel time: 3 hours

On the shores of Michigan’s Lake Macatawa the fairy tale-like town of Holland transports visitors to the Old World with its colorful tulips, twirling windmills and classic Dutch architecture. Embrace the European charm with a bike ride along the town’s paved paths or a stroll down the cobblestone sidewalks of downtown where you can peruse dozens of local shops and eateries.

Immerse yourself in Dutch culture with a tour of the DeZwaan Windmill or a stop inside the Holland Museum. Nelis’ Dutch Village is an interactive theme park celebrating the history and traditions of the Netherlands. If you’re visiting in May, the Veldheer Tulip Gardens are in full bloom with acres of vibrant flowers. The Big Red Lighthouse is a beloved icon in Holland with the best views from the north pier in Holland State Park.

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

17. Spend a day (or more) exploring Madison, Wisconsin

Travel time: 3 hours

There’s so much to see and do in Madison that you might want to turn your day trip into a weekend getaway. The city abounds in art, history, culture, entertainment and nature. Sandwiched between Lake Monona and Lake Mendota, Downtown Madison is home to the Wisconsin State Capitol, the free Chazen Museum of Art, the Madison Children’s Museum and Allen Centennial Garden.

With a broad range of global flavors and farm-to-table eateries, the diverse culinary scene will delight adventurous foodies from the Asian-inspired Ahan to produce-forward Mint Mark. Just beyond the heart of downtown, the Olbrich Botanical Gardens hosts live music, interactive exhibits and educational events among specialty gardens with seasonal and international influences.

If you’re headed to Madison for the weekend, journeying about an hour north with stops at Devil’s Lake State Park and the Wisconsin Dells adds even more fun and fascinating activities to your getaway. Explore 30 miles of hiking trails at Devil’s Lake along with sweeping views from the quartzite bluffs, then make your way to the Wisconsin Dells for year-round family entertainment from waterparks and ski resorts to scenic tours and live theater.

How to get to Madison from Chicago: Amtrak runs a 3 hour and 35 minute bus ride between Union Station and Madison hourly. Drive time by car is just under 3 hours via I-90 W.