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The 18 best day trips from Chicago

Hit the road on these easy day trips from Chicago, where affordable fun awaits busy city dwellers

Photograph: Courtesy of Visit Milwaukee
By Time Out Chicago editors |
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Caught with a bad case of wanderlust and a short supply of vacation time? Look around the Midwest and you'll discover that Chicago is a launching spot for a host of fun, fast escapes. The best day trips from Chicago are filled with awe-inspiring nature, destination-worthy eats and plenty of beer—so be sure to bring a designated driver. Whether you're looking for a Labor Day getaway or a break from the best things to do in Chicago, there are plenty of amazing cities and towns to explore in Wisconsin, Illinois, Indiana and Michigan. Plus, you'll find some of the best hiking near Chicago along the way. Gas up the car (or buy your train ticket) and hit the road on one of the best day trips from Chicago.

RECOMMENDED: The best Chicago staycation ideas

The best day trips from Chicago

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Photograph: John Karpinsky

Milwaukee, WI

Getting to the Cream City requires a painless drive, but if you plan to fully indulge, ditch the car and hop on the BYOB-friendly Amtrak, which will deposit you in the heart of the city in an hour and a half. Start your day with a stack of pancakes and a round of mimosas at SweetDiner. Meander around the Historic Third Ward and hop into home decor shops like Cream City Restoration and Inspired. Seek refuge and treats at the Milwaukee Public Market, where you’ll find a hodgepodge of the city’s best vendors, including blends from Spice House, seafood from St. Paul Fish Company, hand-dipped chocolate from Kehr’s Candies and vino from Thief Wine Shop & Bar. Before catching a train home, walk off the day with a trek along to Lakeshore State Park, a unique 22-acre urban oasis that juts out from the shoreline. —Morgan Olsen

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Virtue Farms
Photograph: Virtue Farms

Fennville, MI

Many Chicagoans wait until fall to venture up to western Michigan’s fruit belt. But there’s a compelling argument to be made for hitting the area a couple of months earlier, when the countryside is tranquil and stone fruits like peaches and cherries are ripe for picking. The petite town of Fennville is a great base for tasting the region’s sweet bounty in a host of iterations. Start off with a slice or two of the good stuff at local favorite Crane’s Pie Pantry, a bakery-restaurant housed in an antiques-strewn converted barn. From here, a five-minute drive will deliver you to the timbered cider houses that anchor idyllic Virtue Farms, founded by former Goose Island brewmaster Greg Hall. Finally, make your way to Salt of the Earth for wood-fired breads and seasonal dishes centered around ingredients sourced within a 50-mile radius. —Cate Huguelet

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South Bend History Museum, Indiana
Photograph: Peter Ringenberg

South Bend, IN

There’s more to South Bend than Fighting Irish football. Check out the city’s cultured side with an afternoon visit to the History Museum, a stately Victorian mansion that was once home to the family of local industrialist and inventor James Oliver. From there, browse the local bounty at the South Bend Farmers' Market, where you can shop everything from artisan breads and doughnuts to farm-fresh fruits and veggies. When hunger strikes, head to Café Navarre, an upscale dining spot housed in a repurposed '20s-era bank. —CH

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Evanston, IL

If you're short on time but craving a day away from the city, hop on the Purple Line and head to Evanston. The sweet college town is located just a few miles north of Chicago, which means you can explore the day away and still be home for dinner. Start the morning at the otherworldly Baha'i House of Worship, an architectural gem located a few miles north, in Wilmette. Wander the pristine grounds before stepping inside the functioning temple, one of the oldest of its kind in the world. Up next: Fill up on colorful macarons, cakes and doughnuts at Bennison's Bakery before checking out the latest exhibit at the Block Museum of Art, a free and inspiring art museum on the campus of Northwestern University. Don't get back on the train without grabbing an expertly crafted tipple at cocktail lounge Ward Eight. —MO

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Christopher Klinge

Madison, WI

Located on an isthmus between two lakes, Madison is a city that’s filled with beautiful sights—in addition to all the cheese and beer you’ve heard so much about. Begin your visit with a scenic tour of the college town on two wheels. You can rent a bike from dozens of BCycle stations, allowing you to make 30-minute trips. The Capital City trail winds around Lake Monona (the smaller of the two lakes) and provides plenty of picturesque stops for an Instagram of the skyline. Now onto that cheese and beer. To drink like a local, head for the Malt House, a “craft beer oasis” that dates back to the Civil War-era and boasts taps from local brewers like New Glarus and Central Waters. Head for Capitol Square to visit Fromagination, where you’ll find artisanal Wisconsin cheeses and knowledgeable cheese mongers to help you make a decision. Take an evening to visit the Terrace at Memorial Union, a lakefront space where you can enjoy brats, beer and live music during the summer months. —Zach Long

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Greenbush Brewery, Harbor County, Michigan
Photograph: Greenbush Brewery Co.

Harbor Country, MI

Just across the Indiana border, Michigan’s lakeside “Harbor Country” is only an hour and a half drive from downtown Chicago. Start at the north end, in Sawyer, where Greenbush Brewing Co. is rapidly taking over the wee main drag, with the original Taproom and the Annex and beer garden across the street both serving Greenbush’s craft brews (we’re partial to the StarChicken IPA). Up next, take the Red Arrow Highway down the lakeshore for great shopping, like hunting through the Harbert Antique Mall or perusing the high-end goods at furniture store Lovell & Whyte. Head back inland to the artsy community of Three Oaks to finish your day at Journeyman Distillery. A $12 tour and tasting nets you samples of 18 different spirits made in the converted corset factory. Plan to sit down for a meal at the distillery’s new Staymaker restaurant afterward; you’ll need some food before getting back on the road to Chicago. —Kris Vire

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Anderson Japanese Gardens
Courtesy: Rockford Area Convention & Visitors Bureau

Rockford, IL

Situated less than 100 miles northwest of Chicago, Rockford is a surprisingly plentiful road trip destination for families. If the kids are in tow, start the day with a visit to the Discover Center Museum, with more than 300 hands-on exhibits focused on everything from flight and art to color and electricity. For a dose of fresh air and nature, wander the grounds on a docent-led tour at Anderson Japanese Gardens, a breathtaking oasis that's filled with towering trees, waterscapes and beautiful blossoms. Everyone in the car will find something to love at Prairie Street Brewing Company, where bar food is elevated through dishes like Korean street tacos, Nashville hot chicken and a wild mushroom wrap. Pick up a few cans of Screw City Light—with notes of fresh-baked bread—to take home and extend your day trip. —MO

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Photograph: courtesy Cedarburg Chamber of Commerce

Cedarburg, WI

Located just 20 miles north of Milwaukee, Cedarburg is an ideal place to wind down and take things slow. The charming small town is brimming with old-world architecture, friendly Midwesterners and culture galore. If you can, plan your trip around one of the town’s seasonal events, with options including CedarBrew Fest, Strawberry Festival and A Cedarburg Christmas—all of which offer ample opportunities to meet local vendors and sample their wares. While you’re not rubbing elbows with the close-knit community at a street fest, make time to walk around the Cedarburg Art Museum, which hosts exhibitions from Wisconsin artists inside a former home that was designed in 1898. If wine bars are more your scene, enjoy a tour and a glass of vino at Cedar Creek Winery, where you can sip syrah, pinot grigio, riesling and more. On your way out of town, make one last stop at Amy’s Candy Kitchen to grab a hand-crafted caramel apple for the road. —MO

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Photograph: Jamie DiVecchio Ramsay

Kankakee County, IL

The Kankakee River has been a treasured area for centuries, occupied by the Illini and Miami tribes in the 17th century. Kankakee River State Park surrounds the river for about 11 miles, totaling to 4,000 acres of protected land. It’s a popular spot for fishing, canoeing, hiking and mushroom hunting. Frank Lloyd Wright fans can visit the B. Harley Bradley House, built in 1900 and billed as the architect’s first Prairie Style home. In the summer, Bears fans can catch a practice at the team’s training camp on the campus of Olivet Nazarene University—KV

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Frank Lloyd Wright Home and Studio
Photograph: James Caulfield

Oak Park, IL

You can't call yourself a Frank Lloyd Wright fanatic until you've spent the day in Oak Park, where you'll find the famed architect's home and studio as well as a smattering of other Prairie-style abodes he designed. If it's your first time, book a 10-stop, two-hour tour through the Frank Lloyd Wright Trust. Now that you've worked up an appetite, grab brunch or dinner at Maya del Sol, where margaritas flow like water and the ceviche is tops. If you have time for one last stop, grab a seat at Kinslahger Brewing Company, a small but mighty taproom pouring lagered brews. —MO

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Frederik Meijer Gardens & Sculpture Park
Photograph: Courtesy Experience Grand Rapids

Grand Rapids, MI

Summer and fall are peak seasons to visit Grand Rapids, but you’d do best to plan ahead and book your visit during ArtPrize, an international art competition in September and October when art is displayed in museums, bars, public parks and hotels. Regardless of when you go, Grand Rapids has you covered on the beer front with dozens of breweries—so be sure to bring a designated driver. First stop: Brewery Vivant for French and Belgian lunch fare. A quick 10-minute drive will put you in the middle of downtown, where you should find parking and hoof it a while. Stop in Madcap Coffee for a post-beer pick me up as you wander south to Grand Rapids darling Founder’s Brewing for your second pint of beer. Finally, grab your car and head to Sovengard for dinner complete with warm, modern vibes and ridiculously photogenic Scandinavian dishes. —Elizabeth Atkinson

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Starved Rock
Photograph: Kathy Casstevens/Starved Rock Lodge

Oglesby, IL

It may not be the mighty Colorado, but Oglesby’s Vermillion River offers the best rafting you’re liable to find within a quick jaunt from Chicago. A 9.5-mile run with Vermillion River Rafting will shoot you over 14 rapids, most of them class I and II. After you’ve handed over your paddle, hop in the car and head up the road to Starved Rock Lodge, where you can catch your breath and lunch on casual fare like burgers or a strawberry pecan salad at the Back Door Lounge. When you feel sufficiently refreshed, hit the hiking trails at adjacent Starved Rock State Park to spot dramatic waterfalls and explore cool glacial canyons. —CH

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New Glarus, WI

You only need to head as far north as Kenosha to snag a case or two of Spotted Cow, Moon Man or one of New Glarus Brewing’s other beloved, only-in-Wisconsin beers (and we’ve been known to drive up to the Mars Cheese Castle for just that purpose). But there are good reasons to make the longer trek to the village of New Glarus, not least to visit the brewery itself. There you can take a self-guided tour of the family-owned operation, sample the wares in the tasting room ($8 for a flight of three or a pint of one, and you can take home the glass) and outfit yourself in the gift shop. But New Glarus, a 19th-century Swiss settlement that still prides itself on its chalet-style look and old-world charm, has more to offer than just (very good) beer. Explore the full range of Swiss heritage at the Swiss Center of North America and see if you have a little Switzerland in you. For the full effect, visit the village during one of its annual events, like June’s Polkafest or September’s Wilhelm Tell Festival and Oktoberfest celebrations. Finish your day by filling up on fondue and wiener schnitzel at Glarner Stube, or have a final New Glarus pint and a flight of Wisconsin cheese with the locals at Puempel’s Olde Tavern. —KV

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Baumgartner’s Tavern
Photograph: Courtesy Green County Tourism

Monroe, WI

If your cheese preferences run to the pungent, you’ll find yourself in good company in charming Monroe, Wisconsin, gateway to a region populous with cheesemakers specializing in varieties like Swiss and nostril-tingling Limburger. For some context, begin your day at the National Historic Cheesemaking Center, where you’ll get a crash course in south central Wisconsin’s cheesy history. Next, continue up the road to the Swiss chalet-style complex that houses Emmi Roth, whose nutty Grand Cru Surchoix took home top honors at the 2016 World Championship Cheese Contest. When you’re ready for lunch, make your way to the unapologetically old-school Baumgartner’s Tavern on Monroe’s pleasant courthouse square and order the infamous specialty: a slab of Limburger on rye crowned with raw red onion shavings. For a chaser, stroll around the block to Minhas brewery. —CH

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Holland, MI
Photograph: Dan Irving

Holland, MI

Once a stronghold of Calvinist separatists who arrived here from the Netherlands in the mid-19th century, the town of Holland continues to celebrate its Dutch heritage. To go Dutch for the day, start off with a breakfast of flaky, almond paste-filled bankets and house-roasted coffee at deBoer Bakkerij. Afterward, head across town to Veldheer Tulip Gardens, where 5 million of the eponymous flowers explode into bloom each spring. When hunger hits, make your way downtown for lunch and a beer at New Holland Brewing, one of the Midwest’s best-loved brewpubs. (Not sure what to sip on? Look for limited-release variations on brewery fave Dragon’s Milk, a bourbon barrel-aged stout, featuring quirky ingredients like maple coffee and peanut butter.) Make a dent in the calorie count with a leisurely stroll around Windmill Island Gardens, a picturesque park centered around a 250-year-old Dutch windmill purchased by Holland residents in the 1960s. —CH

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Lake Geneva, WI
Photograph: Courtesy Visit Lake Geneva

Lake Geneva, WI

Lake Geneva has long been an accessible weekend destination for wealthy suburban Chicago families. But no matter your budget, a quick retreat to this idyllic vacation town is sure to be a blast. The town rests on Geneva Lake, an 8-square-mile body of water made for summertime fun. First things first: Get out on the water. Rent a kayak or paddleboard, or take a wake surfing private lesson at Gage Marine. If you can’t get your sea legs, trek a portion of Lake Geneva’s 21-mile circumference on the Geneva Lake Shore Path and gawk at the century-old mansions the rest on the lakefront shore. When you’re hungry, Egg Harbor Café and Simple Cafe, both in the town center, offer delicious, no-fuss diner eats. If you’re feeling spendy, Baker House, a 19-century mansion-turned-hotel, offers a popular champagne brunch with waterfront views. —Grace Perry

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Slagel Family Farm, Fairbury, Illinois
Photograph: Slagel Family Farm

Fairbury, IL

Observant Chicago foodies may have noticed a couple of names popping up over and over again in the menu sourcing notes that have become de rigueur in these locavore-obsessed times: Kilgus Farmstead (for dairy) and Slagel Family Farms (for a range of meats). Turns out, our favorite chefs’ favorite suppliers sit just a three-mile hop from each other in the central Illinois town of Fairbury. On an hour-long tour of Kilgus, you’ll get acquainted with the farm’s herd of sweet, doe-eyed Jersey cows, learn the ins and outs of milking, and sample freshly spun soft-serve. Bring a cooler and hit the on-site store for Kilgus dairy and meat as well as goods like eggs and honey from nearby producers. Slagel has teamed up with Chicago chefs from spots like Bad Hunter and Publican to put on a program of farm dinners throughout the summer. After an interactive tour and a butchering demo, you’ll retire to a picturesque barn for the main event, a family-style, BYOB meal prepared by the guest chef. —CH

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Michigan City, Indiana
Photograph: Courtesy Indiana Office of Tourism Development

Michigan City, IN

Michigan City: The tiny strip of land keeping Indiana from being completely landlocked. If you’re car-less, this small city is a perfect option for a day trip from Chicago. Hop on the Amtrak at Union Station and you’ll be in Michigan City in just over an hour. Or, take the South Shore Line and you can hop off right at the Indiana Dunes National Lakeshore, 15 miles of gorgeous sand dunes on the southern shore of Lake Michigan. Michigan City proper, too, is filled with great things to do. Stroll through Washington Park all the way out to the Old Light, one of the earliest lighthouses built on Lake Michigan. Hungry? Walk over to Shoreline Brewery, a gem of a microbrewery with a rotating selection of 12 beers on tap and tasty pub grub. You can also sample local flavors at Fiddlehead, which partners with other La Porte country businesses to serve high-quality comfort food. —GP

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