Wine tasting day trips from Chicago

13 wineries and vineyards are within about 110 miles of the Loop in the free FarmScout app, the closest about 35 miles away. Near Chicago the season usually runs year-round - summer and fall weekends are the busiest, harvest is September and October, and many tasting rooms cut back their hours in winter. Here are 5 well-known places to start planning with. The app shows every one on a map, what each farm has this week, hours changes and events, all dated so you know before you go. Updated October 2026.

See all their events and what they offer in the free app.Free to download on iPhone and Android. Know before you go.

5 well-known wineries and vineyards near Chicago

• Four Corners Winery
  Valparaiso · Vineyard / winery
  Season: Open year-round
  About 40 miles from the Loop
• Anderson's Winery and Vineyard
  Valparaiso · Vineyard / winery
  Season: Open year-round
  About 41 miles from the Loop
• Lemon Creek Winery
  Berrien Springs · Vineyard / winery
  Season: Year-round
  About 61 miles from the Loop
• Staller Estate Winery
  Delavan · Vineyard / winery
  Season: Year-round; check website
  About 81 miles from the Loop
• Fenn Valley Vineyards & Wine Cellar
  Fennville · Vineyard / winery
  Season: Year-round
  About 90 miles from the Loop

...and 8 more wineries and vineyards within a day trip of Chicago - plus over 13,000 farms, farm stands, markets and orchards nationwide. See all their events and what they offer in the free app.

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Planning tips

• Check hours before you go. Many tasting rooms cut back to weekends in winter, and some ask you to book a tasting ahead.
• Plan a designated driver, or book a car or tour. Most wine regions are spread out along country roads.
• Make a day of it. Many wineries share their roads with farm stands, orchards and farm markets, and the app shows what else is nearby.

Questions people ask

Where can I go wine tasting near Chicago?

FarmScout lists 13 wineries and vineyards within about 110 miles of the Loop. Well-known ones include Four Corners Winery in Valparaiso, Anderson's Winery and Vineyard in Valparaiso, Lemon Creek Winery in Berrien Springs.

When is wine tasting season near Chicago?

Near Chicago, the season usually runs year-round - summer and fall weekends are the busiest, harvest is September and October, and many tasting rooms cut back their hours in winter. Every farm is different and weather moves it every year, so check what a farm has this week before you drive.

How far do I have to drive from Chicago?

The closest winery in FarmScout is about 35 miles from the Loop in a straight line. Most on this page are within a two-hour drive.

How do I know what is ready before I go?

Every product and event in the free FarmScout app carries the date it was reported, by the farm itself or by our team, so you can see what is ready right now. FarmScout is free to download on iPhone and Android.

Over 13,000 farms, farm stands, markets and orchards nationwide in the free app. See all their events and what they offer.Free to download on iPhone and Android. Know before you go.