A tiered wooden staircase down to the sand at Indiana Dunes National Park. Jon Lauriat/Getty Images
The Windy City attracts visitors from all over the world and no wonder – it's packed with fun things to do, from an incredible live music scene and out-of-this-world dining to museums packed with cultural gems. Wandering through Chicago's neighborhoods and hitting up local bars and restaurants just reminds visitors that they can keep coming back without ever getting bored.
But even with all this to offer, it's worth venturing beyond the city limits to unearth treasures away from the bustling urban streets. In less than 2 hours, you can be whisked away to rolling sand dunes in a national park, acres of vineyards at renowned wineries and charming small towns with the warmest of welcomes. These are the best day trips from Chicago.
1. Shop local in Andersonville
Travel time: 25 minutes
How to travel: by train or bus
Another delightful northern neighbor is electic Andersonville. Known for its Swedish heritage and artistic flair, this charming 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 that sell everything from home goods and pet gear to jewelry and apparel. If you like your day trips with a side of eccentricity, don't miss the curious collection at Wooly Mammoth and the mesmerizing Chicago Magic Lounge. As the home of one of Chicago’s largest LGBTIQ+ 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.
2. Explore Evanston, one of the top college towns in the US
Travel time: 40 minutes
How to travel: by train
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 (Hewn is a hot favorite) 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. See the home of modernist architecture in Oak Park
Travel time: 45 minutes
How to travel: by train
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.
4. Visit iconic film locations in the North Shore neighborhoods
Travel time: 1 hour
How to travel: by train
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. And Kevin's famous home defence wasn’t the only major film to feature the North Shore. Movie buffs can tour locations across Winnetka and neighboring Glencoe that feature in iconic films from the legendary John Hughes, including Ferris Bueller’s Day Off and Sixteen Candles.
The area also offers plenty of natural icons to explore. Take a wander through the sprawling 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: Take the UP-N to Winnetka or Glencoe from Chicago.
5. Spot prairie bison near historic Joliet
Travel time: 1 hour and 20 minutes
How to travel: by train
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 the I-55 or I-57 before joining the I-80 into Joliet.
6. Get into nature at Indiana Dunes National Park
Travel time: 1 hour and 30 minutes
How to travel: by train
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 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 one to two hours, depending on traffic.
7. Admire Harleys and artwork in Milwaukee
Travel time: 1 hour and 30 minutes
How to travel: by train
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, 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 besides New Orleans. Friendly neighborhood taverns pop up are on almost every corner, but 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.
8. Tour the lakeside hamlets of Harbor Country
Travel time: 1 hour and 30 minutes
How to travel: by car
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.
9. Walk a section of the 21-mile Geneva Lake Shore Path
Travel time: 1 hour and 30 minutes
How to travel: by car
Old-money Chicagoans fled to Geneva Lake in the late 1800s to escape the urban heat and relax 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.
10. Experience the “City of Gardens” in Rockford
Travel time: 1 hour and 40 minutes
How to travel: by car
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 pristinely 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 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 the I-290 W and then the I-90 W.
11. Discover outdoor adventures in La Salle County
Travel time: 2 hours
How to travel: by car
Just under two hours from downtown Chicago, you'll find three beautiful state parks 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 the I-80 W.