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 seven easy day trips that are no more than two hours away from the Windy City.
1. Get outside 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 you 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 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.
2. Ogle 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 badass 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 a day to downtown Milwaukee, with a journey time of 90 minutes. By car, take the I-94 for the roughly two-hour trip.
3. 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. 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.
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. 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.
6. 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.
7. Visit 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 its 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.