Where to take a boozy day trip from Chicago

Driving time from Chicago: One and a half hours

We couldn’t dream this up: A hike where you’re encouraged to drink along the way? Yes, this 3.6-mile trail in southwestern Michigan allows you to hike from Round Barn to Tabor Hill Wineries and back, stocking up on more wine and goodies on each end. Choose between easy, moderate, and hard routes depending on what glass you’re on—and don’t be alarmed if you see a few goats on the trail.

Driving time from Chicago: Two and a half hours

As Wisconsin’s first fully certified organic, women-owned and operated brewery, Giant Jones Brewing in Madison’s Willy Street neighborhood has a mission to produce big beers on a small scale. With a rotating selection of barleywines, IPAs, wheat beers and scotch ales on tap, you’ll taste seasonal pops of mint, black currant, pomelo and candied sugar and cake—just watch out for the high ABVs. After tasting a few beers, you can make your way to some of the other distilleries, breweries and Bos Meadery within a few blocks of Giant Jones. And if you need some beautiful scenery, head to one of the many parks along Lake Monona or Lake Mendota.  

Driving time from Chicago: One hour and 40 minutes

When you take a tour of the Indiana Whiskey Company, the staff is proud to give you a no-bullshit rundown of the mechanics, chemical processes and creativity it takes to make locally-sourced whiskey. The 30-minute tour is packed with plenty of jokes and a lot of pride for South Bend and the Hoosier state. To encourage laughter, attendees sample bourbon, Silver Sweet Corn and rye whiskeys before the tour sets off. And if you want to keep drinking during the tour (it’s encouraged!), the team can make you an Old Fashioned or a whiskey sour.

If you want to experience more of South Bend, head four miles north to walk around the University of Notre Dame’s campus. Indiana Whisky Company President Matt Logsdon says you can’t go wrong with a visit to Roselily, Fiddler’s Hearth or a local dive McCormick’s.

Driving time from Chicago: One and a half hours

Take in gorgeous views of Milwaukee (the self-proclaimed “beer capital of the world”) from the water on a Brew City Kayak tour. The Best of Milwaukee tour offers four hours of sightseeing along with beer and sausage tastings. Starting and ending from a boat launch off Water Street, you’ll make three stops, including a brewery tour and tasting at Lakefront Brewery. You can also skip the paddling altogether and visit breweries by foot. The Milwaukee RiverWalk District runs for three miles through the Historic Third Ward and downtown Milwaukee, with some brewpubs and breweries along the way. Head a little further west to the Brewers Hill neighborhood for a spectacular city view from Kadish Park.

Driving time from Chicago: One and a half hours

Feel the wind in your hair and the bloat in your gut as you sample some of the best brews west of Chicago and take in river views by bike on the Fox River Trail, a 44-mile asphalt path stretching from Oswego to Algonquin. Fuel up for your trip with a beer from Oswego Brewing before riding north to the Two Brothers Roundhouse in Aurora and the Penrose Brewing Company in Geneva.

Prefer to be closer to the water? Head to the Aurora Metra station to jump on the Fox River for a Kayak Brews Cruise. You’ll visit Brother Chimp Brewing for a flight of small-batch beers before floating back downstream to the Two Brothers Roundhouse.

Driving time from Chicago: Three and a half hours

The Potosi Brewing Company is your one-stop shop for a day jam-packed with the Midwest’s industrial and brewing history. Just north of the Quad Cities, this brewery was reopened in 2008 after its closure in 1972, and is housed in the same space where it was originally founded in 1852. Start with a visit to The National Brewery Museum or the Great River Road Interpretive Center and Transportation Museum, then take a tour of the brewing facilities while enjoying a tart and refreshing Riverside Radler hefeweizen or the rich Gandy Dancer Porter. There are plenty of places to stay the night nearby if you get carried away, such as the cozy three-room Potosi Portch Front Inn or affordable campsites at the Grant River Recreation Area.

Driving time from Chicago: Two and a half hours

Kalamazoo is more than just a university town and a great weekend getaway spot—it’s also home to Michigan’s oldest craft brewery, Bell’s. Two Hearted Ale tastes even better in the spot where founder Larry Bell first started brewing commercial beer out of 15-gallon soup pots in 1985. Today, Kalamazoo houses several other breweries like Latitude 42 and One Well. Take a West Michigan Beer Tour if you want to visit several breweries over the course of a single day.

Driving time from Chicago: Three hours

You sip your Chardonnay as you look out onto rolling rolling hills of old world grape vines and lush manicured gardens. No, you’re not in France—you’re in Prairie du Sac, Wisconsin, but if the vineyards seem European, it’s because they are. The vineyards at Wollersheim Winery date back to the 1840s, established by a Hungarian nobleman who later helped make California’s wine industry a sensation. The Wollersheim family revived the winery in the ’70s, later opening a distillery next door, where brandy, whiskey, bourbon, gin and absinthe is made.

Driving time from Chicago: One hour

Nothing sounds like a better reward for a long hike through Indiana Dunes National Park than a brewery crawl along Lake Michigan’s South Shore. Stretching from 18th Street Brewery & Distillery in Gary (the second largest brewery in Northwest Indiana), to Hunter’s Brewing and Chesterton Brewery in Chesterton, and further south to Ironwood Brewing and Four Fathers in Valparaiso, these small-batch brewers are among Indiana’s best. You’ll be driving between breweries, so a designated driver is a safe bet.

Driving time from Chicago: One hour and 45 minutes

With gorgeous lakefront views, rolling hills, and charming coastal towns, the 70 miles from Union Pier, MI up to Saugatuck, MI are a stunning backdrop for the region that houses 90% of Michigan’s vineyards. The Lake Michigan Shore Wine Trail boasts 15 different wineries offering tastings that typically provide around five samples for $10. If you can’t pick just one type of beverage, the tasting room at Chill Hill in Baroda, MI allows visitors to mix and match wines, hard ciders, seasonal sangrias and slushies.

Driving time from Chicago: One and half hours

You can thank the Lord for the great beer, lively patio and gourmet bites in this Methodist church-turned-brewery in New Buffalo, MI, just east of Chicago along Lake Michigan’s Southwestern shore. Beer Church Brewing Co. has been turning water into beer ever since it opened in 2017, retrofitting a church built in 1861 with modern brewing equipment. The drafts brewed here boast fitting names like the Crooked Cross cream ale, Bishop Robusto porter and Pontius Pilate New England IPA. Bring home a growler of your favorite—this beer isn’t sold anywhere else.

While you can easily get to New Buffalo by car, we recommend taking the Amtrak, which drops you off just three blocks from the brewery. Stop by Oink’s Dutch Treat Ice Cream & Yogurt Shop or soak up some sun at the New Buffalo City Beach before heading home.

Driving time from Chicago: Two hours

Sit under the twinkling lights of a cozy big top tent while sipping a rich maple bourbon whiskey at Barnstormer Distillery, a Rockford-area distillery with a communal vibe. Bearing a name inspired by the skilled post-World War I aviators that entertained audiences with stunts—and even sometimes bootlegged liquor—this distillery eschews modern equipment in favor of human intuition when crafting its whiskey, rum, and vodka. Come early for an on-site distillation tour and explore the 22-acre property where many ingredients are grown. Then, stick around for an afternoon in the tent, where locals can typically be found mingling and buying shots for one another.