The best day trips from Chicago for an exciting adventure

Driving time from Chicago: One and a half hours

Reaching 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 Johnny cakes and a round of mimosas at Uncle Wolfie's Breakfast Tavern. 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 and vino from Thief Wine Shop & Bar. Before catching a train home, walk off the day with a trek to Lakeshore State Park, a 22-acre urban oasis jutting into the Milwaukee Bay.

Driving time from Chicago: Two and a half hours

Located on an isthmus between two lakes, Madison is a city that’s filled with beautiful sights—along with 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 State 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 your picks. Wrap up the evening with a visit the Memorial Union Terrace, a lakefront space on the University of Wisconsin campus where you can enjoy brats, beer and live music during the summer months. 

Driving time from Chicago: One and a half hours

Escape the crowded Chicago lakefront and head for the sandy shores of the Mitten State, where the water’s warmer and clearer. Soak up some rays and then stroll down Whittaker Street to peruse cute shops and art galleries. Book a spa treatment at The Harbor Grand Hotel for some rest and relaxation; adventurers can rent a kayak or paddleboard from Third Coast Paddling and go exploring along the Galien River. When you need to refuel, grab a seat on The Stray Dog Bar & Grill's bustling patio or sink your teeth into a big, juicy burger at Redamak’s. Make sure to save room for unique ice cream flavors, like Mackinac Island Fudge and Jacked Up Tennessee Toffee, at Oink’s Dutch Treat.

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: One hour and 45 minutes

Golden, sandy beaches and a picturesque shoreline attract visitors to St. Joseph and its twin city Benton Harbor. You can spend an entire day on the water with a rental from Blue Water Boat Rentals, or walk over to the St. Joseph Lighthouses, where guided tours are available every Saturday. If you’re hungry, you won’t have to wander far for good grub, as Silver Beach Pizza—located inside a century-old train depot—slings dependable tavern-style pies. Oenophiles, hit up a variety of vineyards and tasting rooms along the Lake Michigan Shore Wine Trail for some fine Midwestern pours.

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 private wake surfing lesson at Gage Marine. If you can’t find 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 19th-century mansion-turned-hotel, offers a popular champagne brunch with waterfront views.

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 Greenbush Brewing Co. taproom. 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 $15 tour and tasting scores you samples of 13 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.

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 the picking. The petite town of Fennville is a great base for tasting the region’s 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 there, a five-minute drive will land you at Virtue Cider, founded by former Goose Island brewmaster Greg Hall. Make sure to reserve a spot for a guided tasting of four cider styles. Finally, make your way to Salt of the Earth for wood-fired pizza and seasonal dishes made with local and sustainable ingredients.

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 with a sweet treat at Gurnee Donuts, where you can grab ube donuts on weekends. Take some time to 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 a pitstop at 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 a tomahawk ribeye. Those visiting on a Friday can end the night with live music in The Parlor, Primo’s speakeasy-style lounge.

Driving time from Chicago: Three hours

Summer and fall are peak seasons to visit Grand Rapids, but you’d best 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 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 creole bites and a range of beers for every palate. Finally, grab your car and head to Butcher's Union for a dinner complete with prime cuts of beef and pours of whiskey.

Driving time from Chicago: Two and a half hours

Once a stronghold of Calvinist separatists who arrived 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 the Veldheer Tulip Gardens, where over 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 most 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 the Windmill Island Gardens, a picturesque park centered around a 250-year-old Dutch windmill purchased by the city's residents in the 1960s.

Driving time from Chicago: Three hours

With outdoor fun along the Mississippi River, historical sites aplenty, boutique shops, art galleries and imaginative trolley tours, it’s easy to see how Galena would be a favorite for many visitors. Start your day with burritos and mimosas at Otto’s Place, then 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 Uly’s Dark Chocolate Oatmeal Stout while listening to live music and feasting on a bison burger or a giant pretzel with beer cheese and house mustard.

Driving time from Chicago: Two and a half hours

Chances are you’ve already heard of New Glarus thanks to the town’s eponymous brewery—which offers free self-guided tours Tuesday through Saturday and a lovely beer garden—but there are plenty of reasons to visit “America’s Little Switzerland” besides 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 annual Heidi Folk Play Festival. 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 minigolf course, featuring Alpine-themed obstacles and friendly goats.

Driving time from Chicago: One hour and 15 minutes

Fair Oaks, Indiana, is more than just an exit off the long stretch of Indiana’s notoriously uneventful I-65. Under a beaconing silo, Fair Oaks Farms offers a chance for city dwellers to learn, explore and taste the heartland’s agricultural roots. Eat lunch or dinner at farm-to-table spot Farmhouse Restaurant or pack your own picnic and explore the grounds. While most educational attractions and activities—like storytime and learning how to milk a cow—are family-friendly, you don’t have to be a kid to get excited about spotting cows, pigs, chickens and other livestock, and all ages will surely enjoy homemade ice cream and grilled cheese from the Cowfe. 

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 300 hands-on exhibits focused on everything from light and art to color and electricity. For a dose of fresh air and nature, wander through the Anderson Japanese Gardens, a breathtaking 12-acre oasis brimming 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 Baja-style shrimp tacos, Cajun mac ‘n cheese and poke bowls. On your way out, pick up a few cans of Screw City Light—with notes of fresh-baked bread—to take home and extend your day trip.

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 "farm to foam" brews at Tangled Roots Brewing Company in nearby Ottawa. 

Driving time from Chicago: One hour and 15 minutes

About an hour north of Chicago sits this Wisconsin town filled with a plethora of things to do. Within a mile radius of the downtown area are five museums—you can gaze at dinosaur fossils and learn about the link between prehistoric reptiles and birds at the Dinosaur Discovery Museum, or explore how the Civil War affected people on the western front at the Civil War Museum. From spring until fall, visit the Southport Lighthouse and climb 72 steps to the top for unparalleled views of Kenosha and, on a clear day, the Chicago skyline. If it’s summertime, you must check out the Bristol Renaissance Faire, where you’ll find a recreated 16th century port city populated with fairgoers dressed as knights, maidens and much more. After you’ve worked up an appetite, head over to Frank’s Diner, an almost century-old restaurant housed inside an old railway car. Don’t forget to grab some cheeses and New Glarus beers at the famed Mars Cheese Castle on the way home.

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.

Driving time from Chicago: One and a half hours

The Kankakee River region has been a treasured area for centuries, notably 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.

Drive time from Chicago: 30 minutes

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. Once you've worked up an appetite, grab a sweet treat at Spilt Milk Pastry or a full meal at Maya del Sol, where margaritas flow like water and the ceviche is tops. Have time for one last stop? Grab a seat at Kinslahger Brewing Company, a small but mighty taproom pouring lagered brews.

Driving time from Chicago: One hour and 15 minutes

Zion’s Illinois Beach State Park is one of the best places for camping outside of Chicago. Beyond the 4,160-acre nature haven along the Wisconsin-Illinois border, you’ll find good brews—of both caffeinated and boozy persuasions—and unique pieces of history. First, sip coffee from a quirky mug from the in-house collection of mismatched wares at It’s All Good Coffee in downtown Zion. Follow up with a tour of the Shiloh House, a historic 1901-era mansion housing the Zion Historical Society and former residence of Zion’s founder, Dr. John Alexander Dowie. There, learn more about Dr. Dowie, a Scottish-Australian minister who founded Zion as a planned religious utopia and committed large-scale fraud. 

Head just north of Zion to Winthrop Harbor’s North Point Marina, one of the largest along the Great Lakes. Weather permitting, rent a kayak or stand-up paddle or stay on land for live music, good views and craft beers at Harbor Brewing Co. If you're fishing for some bragging rights, stand with one foot on either side of the state border at North Point Beach.

Driving time from Chicago: Two and a 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 Museum, 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 Downtown Historic Courthouse Square and order the infamous specialty: a slab of Limburger on rye crowned with mustard and sliced red onions. For a boozy chaser, stroll around the block to Minhas brewery.

Driving time from Chicago: One hour

The Village of Lemont emerged during the construction of the canal connection the Illinois River and Lake Michigan, which also spurred the growth of nearby limestone quarries that supplied materials for iconic Illinois landmarks such as 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 jonesing 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.

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 vendors flock to the historic downtown to showcase creative takes on the celebrated foods. Stop for a beer at Buffalo Creek Brewing's Bavarian-style taproom or decompress in their 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.

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 marvel 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 scattered across Northwestern University’s campus. Don't get back on the train without grabbing a brew from Sketchbook Brewing Company.

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, where you'll be greeted with 15 miles of gorgeous sand dunes and Lake Michigan's southern shore. 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 like fried lake perch and grass-fed beef burgers.

Driving time from Chicago: 30 minutes 

Head 16 miles north by car or CTA for art, history and nature in downtown Skokie. The village is lined with locally owned shops and restaurants, and is home to the Illinois Holocaust Museum & Education Center. Start your day with an everything bagel with lox from Kaufman’s Bagel & Delicatessen and use the free app Otocast for a self-guided tour of the area’s murals and sculptures. Mid-tour, grab coffee and a savory empanada or SALAMAT! Filipino cookie at Complimentary Cafe. If haven't gotten your fill of art, head east to the north channel of the Chicago River for the North Shore Sculpture Park, a two-mile walkway with over 60 pieces of public art. Download a self-guided tour or plan to roll up to one of free guided tours on Saturdays and Sundays, May through October.

Driving time from Chicago: Two hours

Observant Chicago foodies may have noticed a couple names popping up time and time again in menu sourcing notes: Kilgus Farmstead (for dairy) and Slagel Family Farm (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. During 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 chefs from notable Chicago restaurants to host a slew 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.

Driving time from Chicago: Three and a half hours

Despite boasting a population just shy of 1,700 people, this town west of Madison has a lot going on. Most visitors make the trek 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 assorted oddities, get a taste of traditional Wisconsin hospitality at Arthur’s Supper Club. Theater buffs can take in a show at the American Players Theatre.

Driving time from Chicago: 50 minutes 

Aurora made headlines when WalletHub named the city the happiest place to live in Illinois. Once you pay the state's second-largest city a visit, it’s easy to see why. Easily accessible via Metra, this western Chicago suburb features a walkable downtown with music, festivals, street fairs and ample green space to get your nature fix. Bring along your running shoes or bike—or kayak if floating is your preferred method of sightseeing—and hit the Fox River Valley Trail, a 40-mile paved path running along the eponymous river. Finish the afternoon with coffee or craft beers at Two Brothers Roundhouse, a 1850s-era limestone building listed on the National Register of Historic Places, before heading back downtown for a Broadway show at the Paramount Theater.

Driving time from Chicago: 50 minutes 

If there’s a place that embraces its unique and often complicated past, it’s Joliet. History is intertwined in nearly every aspect of the “City of Stone,” from the limestone facade of the castle-like Bishop Hill Winery to its recreational spots, like the Joliet Iron Works Historic Site, a park that was once the second-largest steel mill in the United States. Names of many local businesses—like Prison City Vintage—even reference the past. Contextualize the city with a visit to the Joliet Area Historical Museum, a collection of over 30,000 artifacts, including memorabilia from the country's first Dairy Queen and Route 66. Afterward, roam the 1858-constructed Old Joliet Prison, a frequent filming location and must-see for TV and movie buffs. Finish off with classic diner food at the on-theme Joliet Route 66 Diner.