Day Trips from Chicago
← All Chicago day tripsDay Trips from Chicago: Wineries & Vineyards
Discover the best wineries and vineyards within driving distance of Chicago, IL. From intimate tasting rooms to sprawling estate vineyards, these destinations make for a perfect day trip or weekend wine getaway. Real drive times, ratings, and booking links included.
12 wineries near Chicago
The Rejoicing Vine Winery
Indianapolis, IN 46278
Just 2 hrs 44 min from Chicago, rated 5.0 stars by 262 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Ridetastic Winery Tours
Stevensville, MI 49127
Just 1 hr 33 min from Chicago, rated 5.0 stars by 139 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Spirits of Norway Vineyard
Franksville, WI 53126
Just 1 hr 22 min from Chicago, rated 4.9 stars by 138 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Golden Muse Winery
Baroda, MI 49101
Just 1 hr 33 min from Chicago, rated 4.8 stars, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Running Vines Winery
Chesterton, IN 46304
Just 56 min from Chicago, rated 4.8 stars by 294 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Sable Creek Winery
Romeoville, IL 60446
Just 46 min from Chicago, rated 4.8 stars by 137 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Hickory Creek Winery
Buchanan, MI 49107
Just 1 hr 32 min from Chicago, rated 4.8 stars by 332 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Wollersheim Winery & Distillery
Prairie du Sac, WI 53578
Just 2 hrs 42 min from Chicago, rated 4.8 stars by 898 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Timber Hill Winery
Milton, WI 53563
Just 1 hr 51 min from Chicago, rated 4.8 stars by 518 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Galena Cellars Vineyard
Galena, IL 61036
Just 2 hrs 41 min from Chicago, rated 4.7 stars by 238 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Apple Works Winery
W179N12536 Fond du Lac Ave, Germantown
Just 1 hr 51 min from Chicago, rated 4.7 stars, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Staller Estate Winery & Distillery
Delavan, WI 53115
Just 1 hr 50 min from Chicago, rated 4.7 stars by 270 visitors, known for excellent food, drink, and local flavor.
Best time to visit: Year-round, but harvest season (Sep-Oct) is peak for wineries and farm-to-table.
Frequently Asked Questions About Wineries Day Trips from Chicago
What are the best wineries near Chicago, IL?
The best wineries near Chicago include award-winning vineyards, tasting rooms, and estate wineries all within a few hours' drive. Check the destination cards above for ratings, drive times, and direct booking links.
Are there wine tours near Chicago?
Yes. Many wineries near Chicago offer guided tastings and tours. Use the "Book Activities" button on any card to find wine tour packages through Viator and GetYourGuide, which often include transportation and multi-winery stops.
How far are the closest wineries from Chicago?
The closest wineries to Chicago are typically 45 minutes to 2 hours away, making them ideal for a day trip. Some regions farther out (2-3 hours) are worth an overnight stay for a full wine weekend.
What is the best time to visit wineries near Chicago?
Fall harvest season (September-October) is peak time for wineries, with grape picking and crush events. Spring and summer offer beautiful vineyard scenery. Most tasting rooms are open year-round, and winter visits mean smaller crowds and more personal attention.
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