The best wineries near Chicago for scenic sipping

Driving time from Chicago: One hour

This Plainfield winery uses grapes sourced from Illinois, Michigan, Missouri, New York and California to make a wide variety of dry and sweet wines you can taste alongside a plate of cheese or charcuterie. If you’re looking for some summer fun, chill on the patio with a wine slushie and order a s’mores tray that allows you to roast the marshmallows right at your table. The spot also regularly hosts special events such as trivia, bingo and live music.

14912 S Eastern Ave, Plainfield, IL

Driving time from Chicago: One and a half hours

Many of the varieties available at Oswego’s Fox Valley Winery are produced with grapes from Illinois vineyards, making these whites and reds hyperlocal. Try them at the tasting room where you’ll also find works from local artists on display, including wood carvings and pottery. Depending on the weather, you can sip your bold Petite Sirah inside or hang out on the patio and nibble on artisan cheese while having a wine slushy. Expand your palate with a tasting or by signing up for wine clubs focused on dry or sweet vino.

5600 U.S. Route 34, Oswego, IL

Driving time from Chicago: Three hours

Visit this vineyard, where the winery’s grapes are grown, and then try the finished product in Galena Cellars’ renovated tasting room while snacking on local cheese, sausage and crackers. You’re also welcome to bring a picnic (and even your dog) and sip a glass in the winery’s large outdoor seating space. The vineyard boasts a guest suite and guest house if you want to stay the night after you get done tasting. Every September, Galena Cellars hosts its Fall Harvest Festival, which features grape stomping, live music and horse-drawn carriage rides.

4746 N Ford Rd, Galena, IL

Driving time from Chicago: One and a half hours

There's a lot going on at this winery (and distillery, and brewery), which takes its name from the Amish round barn that serves as the centerpiece of a sprawling estate where the owners grow grapes, cherries and other fruit used to make wines you can enjoy on a deck or lawn overlooking the vineyard. Catch outdoor concerts on the weekend from May through October while snacking on pretzel bites with Kolsch beer cheese or other seasonal dishes from their food truck. Order one of Round Barn's beer and spirits if you’re visiting with someone who simply isn’t that into wine.

10983 Hills Rd, Baroda, MI

Driving time from Chicago: 45 minutes

The 1912 home of Roselle’s namesake Colonel Roselle Hough has hosted Lynfred Winery since 1979 and now brings more than 100,000 visitors to the village each year to sample its hundred varieties of wine. Stop in for a glass or wine tasting that's crafted to pair perfectly with a cheese flight. If you plan ahead, you can reserve a private wine tasting for two that comes with charcuterie and homemade bread, plus sweet treats. If you can’t make it to Roselle, you can also try the wines at Lynfred’s Wheeling or Highland Park locations.

15 S Roselle Rd, Roselle, IL

Driving time from Chicago: One and a half hours

Studio Winery uses grapes from its own small vineyard and other Midwestern producers to make small batch wines and vermouth to please any palate. The distillery section of the business was added during the pandemic, so now you can visit the tasting room for a cocktail made with moonshine, vodka, rum, gin, brandy or whiskey. The space is also a working art and recording studio, and you’ll catch live classic rock and blues music every Friday and Saturday night.

401 E Sheridan Springs Rd, Lake Geneva, WI

Driving time from Chicago: 45 minutes

Broken Earth Winery grows its grapes and bottles its wines in Paso Robles, California, but you can try them at this Long Grove wine bar. Taste a variety of styles with a flight of four 2.5-ounce pours while nibbling on cheese and charcuterie or ordering in from a local restaurant. Catch live entertainment most weekends, ranging from stand-up comedy to Elvis tributes. Broken Earth also offers spirits and local craft beers you can enjoy at the bar or on the patio.

219 Robert Parker Coffin Rd, Long Grove, IL

Driving time from Chicago: Two and a half hours (Cambridge), two hours and 45 minutes (Madison)

The Cambridge Winery Event Center has become a popular destination for weddings held in its vineyard gazebo, but you don’t need an invitation to make a trip. Stop by on Wednesday nights when you’ll get $10 off any bottle of wine with the purchase of two pizzas, adorned with tasty toppings like barbecue chicken and pepperoni. You can also visit Cambridge Winery’s Madison tasting room and try a flight of red, white or sweet wines for $10, a price that’s waived if you buy two bottles to take home. Join the wine club at either location to earn discounts and access to special events.

600 Kenseth Way, Cambridge, WI and 1001 S Whitney Way, Madison, WI

Driving time from Chicago: One hour

The 130-year-old castle-like building housing Bishops Hill had been a brewery and the headquarters for the Joliet Catholic Diocese before a group of friends bought it with the goal of bringing a European-style winery to the Chicago suburbs. Sample nine wines for $20 or sign up for a wine and charcuterie pairing with sommelier Linda Kloss, who will teach you the basics of tasting. Once a month the bar hosts a Saturday yoga session that includes a post-class glass of wine to help you relax. The castle grounds can also be booked for events.

310 Bridge St, Joliet, IL

Driving time from Chicago: One hour and 15 minutes

This family-owned winery offers a mix of dry and sweet small batch wines made with grapes grown around the country that are fermented and bottled in Valparaiso. Visit LambStone’s tasting room for a sampling with a cheese board or food from Albano’s Pasta. If you buy a bottle a month, you can join the wine club for early access to new releases and a discount on all purchases.

1555 W Lincolnway, Valparaiso, IN

Driving time from Chicago: One and a half hours

Offering more than 35 varieties, Prairie State’s wines range from dry reds to novelties like elderberry wine and white wine sweetened with local honey. Try a glass while sitting on the patio and enjoying a bite from the kitchen like ham sliders with gruyere or a smoked turkey panini with pepper jack. You can catch live music in the garden every other weekend through the end of fall.

222 W Main St, Genoa, IL

Driving time from Chicago: 45 minutes

Head to Long Grove for a real wine education and embark on a tour of the Valentino Vineyards, where 20 varieties of grapes are grown—you’ll then have the opportunity to sample the finished product as part of a tasting and wine appreciation seminar. Reservations are required for the vineyard tour and seminar, and recommended if you want a tasting of five of their wines aged in French and American oak barrels, including red and white ports perfect for pairing with chocolate-dipped strawberries.

5175 Aptakisic Rd, Long Grove, IL

Driving time from Chicago: One hour

Acquiviva lets you explore the full winemaking process by touring the vineyards and the wine production facility. There are 30- and 60-minute options, including one guided by winemaker Sergio Benavides that offers wine paired with meat and cheese. You can also just drop in for a casual tasting or try a bottle while dining on traditional Italian fare at the on-site restaurant. Acquaviva is a popular venue for weddings and other parties, so it’s worth calling ahead just to make sure the place isn’t booked up before you hit the road. Acquiviva also has a restaurant and tasting room in Batavia.

47W614 Route 38, Maple Park, IL

Driving time from Chicago: One hour

Get everything you need to make wine and beer at home at this shop with a tasting room where you can try a wide variety of drinks made on site, from chardonnay to barrel-aged cider to sparkling mead. Craft your own flight and then bring home some bottles plus a wine kit to get you going. The bar also offers a selection of classic cocktails, Belgian beers on tap, and neat whiskey and bourbon pours.

225 W Main St, St. Charles, IL

Driving time from Chicago: Two hours

Part of the Judson Fruit Farm, which has been run by the same family since 1852, Fruit Hills features four acres of grapes that can handle the cold like Itasca and Petite Pearl. They also make hard ciders from the apples grown on site, which you can get fresh in the fall, and bring in grapes and juices to produce popular wine varieties that can't survive the Midwest weather, like riesling and tempranillo. Come on Sundays to listen to live music on the deck while sipping a flight.

55503 State Road 15, Bristol, IN

Driving time from Chicago: One hour and 15 minutes

Grapes from Michigan and California are used to make more than 30 varieties of wine at Shady Creek Winery. Try a flight paired with three small bites or come up with your own combos with their menu of pizzas, panini and salads. Catch live music on the weekend and check the calendar for special events like candle making workshops, trivia or wine pairing dinners.

2030 Tryon Rd, Michigan City, IN

Driving time from Chicago: One hour

Located just a few miles from the Indiana Dunes National Park, Running Vines uses grapes from around the world to make wines, which you can try in sweet, variety or dry flights or a tasting of your own design. The spot regularly hosts trivia and live music, so gather a group to share some wood-fired pizza and cheese and charcuterie boards along with wine slushies.

101 Broadway, Chesterton, IN

Driving time from Chicago: One hour

Village Vintner crafts about 35,000 bottles of wine each year and you can get a taste of seven varieties of either dry or fruit wines in their tasting room. You can also get a glass in its restaurant, where it’s used to steam mussels with Italian sausage. The space includes a small brewery and the draft beers are available in sizes ranging from tasters to growlers. Dessert wines are only available by the bottle, so grab one for a sweet treat at home. 

2380 Esplanade Dr, Algonquin, IL

Driving time from Chicago: One hour

Try a selection of dry and sweet red and white wines accompanied by panini, flatbread or a cheese plate, finishing your experience with a glass of port or dessert wine. Anderson’s Winery’s recently renovated tasting room is only open Friday through Sunday, hosting live music from 2-5pm every Saturday and Sunday. When the weather is nice, you can have your drinks and snacks in the garden or explore the 43-acre property to find the perfect place for a picnic.

430 E US Highway 6, Valparaiso, IN

Driving time from Chicago: Two hours

Apple Barn Orchard & Winery offers u-pick strawberries, apples and pumpkins from June to October, and turns the fruit they grow into wines. Stop into the farm store for a free tasting of varieties including Honey Crisp Apple Harvest and Strawberry Jewel—tips are donated to the Leukemia Lymphoma Society of Wisconsin. You can buy a glass to sip on the patio along with a seasonal freshly baked treat like apple cider doughnuts or pumpkin chocolate chip cookies.

W6384 Sugar Creek Rd. Elkhorn, WI

A restored 1870s farmhouse serves as the tasting room for Four Corners Winery, and folks can also have weddings in a renovated barn. The space offers rustic charm, with a deck overlooking the vineyards where you can try a selection of reds, whites, rosés or fruit wine made with cherries or peaches. Along with a large menu of small plates, salads and flatbreads, Four Corners serves beer, cider, wine slushies and mocktails so no one is left out. The venue regularly hosts live music as well as other events, including painting nights and charcuterie styling workshops.

294 E 600 N, Valparaiso, IN

Driving time from Chicago: One hour

This family-owned winery offers more than 15 varieties, including classic styles like riesling, malbec and merlot, and fruit wines made with raspberries, peaches and apples. Try a glass or get a flight while snacking on a board of cheese, charcuterie and sweets in the shady outdoor area. Gilted Edge periodically hosts live music and serves sangria and spritzes made with its wines.

9396 Plattville Rd, Newark, IL

Driving time from Chicago: One and a half hours

Spirits of Norway uses hardy, cold-resistant grapes to make its wine and you can see them growing when you book a tour, which also includes a stop in the winery to see how the bottles are crafted. You can then taste the finished product—choosing from reds, whites or a mix of both—paired with a charcuterie board. Take home a bottle of your favorites along with some Wisconsin cheese.

22200 W Six Mile Rd, Franksville, WI

Driving time from Chicago: One and a half hours

The 12-acre, family-owned vineyard uses 40 varieties of grapes to blend about 20 varieties of red and white wines plus seasonal fruit wines made with cherries and pumpkin. Visit the century-old farm on the weekend for a self-guided tour and a $20 tasting of five wines that includes a souvenir glass. The bottles are all priced around $15 so you can buy a few of your favorites to take home without breaking the bank.

11582 Waterman Rd, Waterman, IL