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The best day trips from Chicago

Explore small-town breweries, bakeries and artisan shops when you embark on these easy day trips.

Emma Krupp
Edited by
Emma Krupp
Written by
Time Out Chicago editors
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Making big travel plans can be difficult (and not to mention expensive). Luckily, you don’t need a plane ticket or even a hotel reservation to indulge in a fun change of scenery—a simple day trip from Chicago is cheap and easy. Whether you’re looking to spend the day basking in the sun at beaches along Lake Michigan, hiking near Chicago through a state park or tasting your way through the best beer and cheese Wisconsin has to offer, these quick jaunts from Chicago are just a few hours away by car or train. Make plans to explore everything the Midwest has to offer on the best day trips from Chicago. 

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Best day trips from Chicago

Driving time from Chicago: One and half hours

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 The Home Market or fun specialty shops like MOD GEN. Seek refuge and treats at the Milwaukee Public Market, where you’ll find a hodgepodge of the city’s best vendors, including blends from The 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. 

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Morgan Olsen
Global Food & Drink Editor
Fennville, MI
Photograph: Virtue Farms

2. Fennville, MI

Driving time from Chicago: Two hours and 20 minutes

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 and winery housed in a 150-year-old barn. From here, a five-minute drive will deliver you to Virtue Farms, founded by former Goose Island brewmaster Greg Hall. Reserve a spot for a guided trail tour that includes a can of cider. Finally, make your way to Salt of the Earth for wood-fired pizza and seasonal dishes made from scratch with local and sustainable ingredients.

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South Bend, IN
Photograph: Peter Ringenberg

3. South Bend, IN

Driving time from Chicago: One hour and 45 minutes

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. 

Driving time from Chicago: Two and half hours

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 snapshot 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 cheesemongers to help you make a decision. Take an evening to visit the Terrace at Memorial Union, a lakefront space on the University of Wisconsin campus where you can enjoy brats, beer and live music during the summer months. 

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Gurnee, IL
Photograph: Courtesy Six Flags Great America

5. Gurnee, IL

Driving time from Chicago: One hour

Located right off I-94, the village of Gurnee is a shopping and entertaining hub that draws 23 million visitors each year—including plenty of nearby Chicagoans. Start your day by fueling up with the brunch buffet at The Chocolate Sanctuary, where you can pile your plate with housemade bagels with lox, shrimp cocktail and chocolate-dipped strawberries. Spend some time digesting while you stroll around Gurnee Mills, which hosts more than 160 stores selling everything from sporting goods to home decor. Thrill seekers won’t want to miss Six Flags Great America, where you’ll find high-speed roller coasters and intense drop rides. On a hot day, you’ll want to plunge down the water slides and splash around the wave pool at Hurricane Harbor. If you can resist indulging in funnel cakes or turkey legs at the park, save your appetite for Primo Italian American Cuisine, where the dinner menu features black truffle ravioli and beef wellington. If you come on a Friday, you can end your night with live music in The Parlor, Primo’s speakeasy-style lounge.

Oglesby, IL
Photograph: Kathy Casstevens/Starved Rock Lodge

6. Oglesby, IL

Driving time from Chicago: Two hours

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. Unwind from your nature adventures by grabbing a nostalgic treat at The Rootbeer Stand or check out the "farm to foam" Tangled Roots Brewery and Lone Buffalo brewpub in nearby Ottawa. 

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Harbor Country, MI
Photograph: Greenbush Brewery Co.

7. Harbor Country, MI

Driving time from Chicago: One and a half hours

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 you can visit the original taproom of Greenbush Brewing Co. Pair a pour of Star Chicken Shotgun IPA with some barbecue or Cajun fare. Up next, take the Red Arrow Highway down the lakeshore for great shopping, like hunting through the Harbert Antique Mall. Head back inland to the artsy community of Three Oaks to finish your day at Journeyman Distillery. A $13 tour and tasting nets you samples of 12 different spirits made in the converted corset factory. Plan to sit down for a meal at the distillery’s Staymaker restaurant afterward; you’ll need some food before getting back on the road to Chicago. 

Rockford, IL
Courtesy: Rockford Area Convention & Visitors Bureau

8. Rockford, IL

Driving time from Chicago: Two hours

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 Discovery Center Museum, which boasts more than 250 hands-on exhibits focused on everything from light and art to color and electricity. Online reservations are required, so grab your tickets before you hit the road. For a dose of fresh air and nature, wander through the Anderson Japanese Gardens, a breathtaking 12-acre oasis that's filled with winding pathways, koi-filled ponds, and colorful plants. 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, Cajun mac ‘n cheese and wild mushroom quesadillas. Pick up a few cans of Screw City Light—with notes of fresh-baked bread—to take home and extend your day trip. 

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Morgan Olsen
Global Food & Drink Editor
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Cedarburg, WI
Photograph: courtesy Cedarburg Chamber of Commerce

9. Cedarburg, WI

Driving time from Chicago: Two hours

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 the Wine & Harvest Festival and Oktoberfest—all of which offer ample opportunities to meet local vendors and sample their wares. When 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, head to Cedar Creek Winery, where you can sip your way through a $10 wine fight or enjoy a seasonal wine and cheese tasting for $25. 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. 

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Morgan Olsen
Global Food & Drink Editor
Kankakee County, IL
Photograph: Shutterstock

10. Kankakee County, IL

Driving time from Chicago: One and half hours

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 bicycling. Frank Lloyd Wright fans can visit the B. Harley Bradley House, built in 1900 and billed as the architect’s first Prairie Style home. Bring the kids to Perry Farm Park, which features a children’s museum, nature trails, playground, and picnic areas. 

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Oak Park, IL
Photograph: James Caulfield

11. Oak Park, IL

Drive time from Chicago: Half an hour

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 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. 

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Morgan Olsen
Global Food & Drink Editor

Driving time from Chicago: Three hours

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 poutine and a German- or Belgian-style beer. A quick 10-minute drive will put you in the middle of downtown, where you should find parking and hoof it a while. Stop at Madcap Coffee for a post-beer pick me up before heading to City Built Brewing for Puerto Rican snacks and a range of beers for every palate. Finally, grab your car and head to The Søvengård for a dinner complete with warm, modern vibes and ridiculously photogenic Scandinavian dishes. 

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Monroe, WI
Photograph: Courtesy Green County Tourism

13. Monroe, WI

Driving time from Chicago: Two and half hours

If your cheese preferences embrace the pungent, you’ll find yourself in good company in charming Monroe, Wisconsin, gateway to a region teeming 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, head to the Alp and Dell cheese store to browse more than 100 varieties of cheese, mostly from local producers, and all the wine, beer, and sausage you’d want to pair them with. When you’re ready for lunch, make your way to the unapologetically old-school Baumgartner’s Cheese Store & Tavern on Monroe’s pleasant courthouse square and order the infamous specialty: a slab of Limburger on rye crowned with mustard and sliced red onions. For a chaser, stroll around the block to Minhas brewery. 

Lemont, IL
Photograph: Courtesy The Forge: Lemont Quarries

14. Lemont, IL

Driving time from Chicago: One hour

The Village of Lemont developed as part of the construction of the canal linking the Illinois River and Lake Michigan, which also led to the discovery and development of the limestone quarries used to supply materials for iconic Illinois buildings like the Chicago Water Tower. Today, you can hop on the Metra and visit the Heritage Quarries Recreation Area, where you can walk, bike or fish along the I&M Canal (just be sure to look out for the many water birds drawn to the area). If you’re hoping for a bit more excitement, visit The Forge: Lemont Quarries. The adventure park features laser tag, a zipline and ropes courses for all ages and skill levels. Afterwards, head to the village’s historic downtown area to visit Pollyanna Brewing Company and try The Full Lemonty, their signature golden ale. You can also find the brewery’s beer on tap at Wooden Paddle, where you can watch your wood-fired pizza and other small plates being prepared before they hit your table.

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Holland, MI
Photograph: Dan Irving

15. Holland, MI

Driving time from Chicago: Two and a half hours

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 five 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, enriched with ingredients like cocoa nibs and peanut butter.) Wrap up your trip 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. 

Long Grove, IL
Photograph: Courtesy Buffalo Creek Brewing

16. Long Grove, IL

Driving time from Chicago: 45 minutes

Located 35 miles northwest of Chicago, Long Grove was founded in the 1800s by German farmers, and many of the town’s original homes and buildings are still standing. Try to visit Long Grove during one of its many delicious festivals such as Apple Fest or Strawberry Fest, when local chefs and other vendors flock to the historic downtown area to offer numerous versions of the spotlighted food. Stop by Buffalo Creek Brewing and have a beer in their Bavarian-style taproom or in the Biergarten, which hosts live music and food trucks during the summer. Before you hit the road, swing by Long Grove Confectionery to pick up some peanut brittle or their signature Giant Myrtle, made with roasted pecans or cashews topped with caramel and milk or dark chocolate.

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Lake Geneva, WI
Photograph: Courtesy Visit Lake Geneva

17. Lake Geneva, WI

Driving time from Chicago: One hour and 45 minutes

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 from Clear Water Outdoor, 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 that rest on the 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. 

Driving time from Chicago: 40 minutes

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 outdoor exhibition at the Block Museum of Art and taking a free art walk to see the 16 sculptures placed in public spaces on Northwestern University’s campus. Don't get back on the train without grabbing a brew from Temperance Beer Co. If you have the time, take a $10 brewery tour that includes samples and a souvenir pint glass. 

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Morgan Olsen
Global Food & Drink Editor
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Michigan City, IN
Photograph: Courtesy Indiana Office of Tourism Development

19. Michigan City, IN

Driving time from Chicago: One hour and 15 minutes

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 Park, 15 miles of gorgeous sand dunes on the southern shore of Lake Michigan. Michigan City proper, too, is filled with great things to do. Visit Washington Park where you can picnic on the beach or check out the lions, wolves, and other animals from around the world at the Washington Park Zoo. Hungry? Walk over to Shoreline Brewery, a gem of a microbrewery with a rotating selection of beers on tap and tasty pub grub. You can also sample local flavors at Fiddlehead, which serves high-quality comfort food including fried lake perch and grass-fed beef burgers. 

Galena, IL
Photograph: Jamie Loso

20. Galena, IL

Driving time from Chicago: Three hours

While this city on the Mississippi River might be best known for its resorts, you don’t need to stay the night to enjoy its mix of historical sites and outdoor activities. Start your day with brunch at Otto’s Place, where you can enjoy biscuits and gravy featuring housemade buttermilk biscuits and locally sourced sausage with a bloody mary or mimosa. Head across the Galena River to Nuts Outdoors and rent an electric bike to ride along the trails and into town. Take a tour of the city’s proudest attraction, the Ulysses S. Grant Home, which was gifted to the 18th president when he returned from fighting in the Civil War. If you want to learn more, you can visit the Galena & U.S. Grant Museum, which also features an offsite working blacksmith shop. That history is also on display at Galena Brewing Company, where you can sip Ult’s Dark oatmeal stout while listening to live music and feasting on a beer brat with sauerkraut and housemade mustard.

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Fairbury, IL
Photograph: Slagel Family Farm

21. Fairbury, IL

Driving time from Chicago: Two hours

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 Dove's Luncheonette and Gaijin to put on a program of farm dinners throughout the summer and fall. 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. 

New Glarus, WI
Photograph: Shutterstock

22. New Glarus, WI

Driving time from Chicago: Two and a half hours

Chances are you’ve already heard of New Glarus thanks the town’s eponymous brewery—which offers self-guided tours Monday through Friday and a lovely beer garden—but there are plenty of reasons to visit “America’s Little Switzerland” other than beer. This charming, walkable town features a variety of tempting shops, hearty restaurants and themed events celebrating the town’s Swiss history and culture like the Heidi Folk Festival and the Wilhelm Tell Festival in June. Be sure to grab a nut horn at the New Glarus Bakery, and get your fondue fix at the Chalet Landhaus restaurant. If you visit between May and October, don’t miss the seasonally-open Swissland mini golf course, featuring Alpine-themed obstacles and friendly goats. 

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Spring Green, WI
Photograph: Torey Byrne

23. Spring Green, WI

Driving time from Chicago: Three and a half hours

Despite boating a population just shy of 1,700 people, this town west of Madison has a lot going on. Most visitors are here to visit one of two sprawling complexes: Taliesin, the estate and studio of legendary architect Frank Lloyd Wright, or the infinitely weirder House on the Rock, the brainchild of artist Alex Jordan where curious travelers can explore rooms on rooms of infinity mirrors, dollhouses, nostalgic cars, circus ephemera and the world’s largest indoor carousel. When you’ve had your fill of architecture or funky assorted collections, grab scratch-made pizza and cocktails at the landmark Last Leaf Public House or get a taste of traditional Wisconsin hospitality at Arthur’s Supper Club. Theater buffs can take in a show at the American Players Theatre, whose incoming season includes American theater icons old (A Raisin in the Sun) and new (Tarell Alvin McCraney’s The Brothers Size).

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