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Top Chicago Wine Tasting & Winery Tours

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7 Chicago Wine Tasting & Winery Tours

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Did you know?You can reserve your spot today and pay when you're ready.
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Did you know?
You can reserve your spot today and pay when you're ready.Learn more

Duneland Wine Country with Gourmet LunchWine Tasting & Winery Tours

Duneland Wine Country with Gourmet Lunch

star-5
Discover the wines and farm-to-table cuisine of the Indiana dunes on a full-day gourmet tour from Chicago with an experienced vintner. Visit a series of three wineries for guided tastings of wines made from cold hardy, locally-grown grapes. Explore a unique landscape of quaint villages while learning the terroir of Illinois wines, then enjoy a luxurious lunch of contemporary farm-fresh fare in Chesterton, whose old-fashioned Main Street is a slice of small town Americana in the heart of Duneland.
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Booked by 8 travellers
Small group
  • 7 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD197.34 
From  
USD197.34 
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  • 7 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Fox River Wine Country with Gourmet LunchWine Tasting & Winery Tours

Fox River Wine Country with Gourmet Lunch

Raise a glass to the burgeoning winemaking industry of Illinois’ Fox River Valley during this 6-hour tasting tour and gourmet lunch. Taste the unique ‘terroir’ of the Midwestern wines grown in this scenic river region as you stop for tastings at three local wineries, enjoying up to seven samples at each stop. During the trip you’ll also have time for a leisurely gourmet meal to help wash down your wine. An experience winemaker host, plus drop-off at select Chicago hotels is also covered.
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Small group
  • 6 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD169.60 
From  
USD169.60 
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  • 6 hours
  • Reserve Now & Pay Later
  • Free Cancellation

SW Michigan Wine Country with Gourmet LunchWine Tasting & Winery Tours

SW Michigan Wine Country with Gourmet Lunch

star-5
Slip away from the hustle and bustle of Chicago to enjoy the idyllic scenery and burgeoning wine industry of Southwestern Michigan on this 8-hour excursion. This beautiful region is renowned for its bountiful agriculture, beautiful beaches and now, an up-and-coming wine-making community. Stop by three wineries, learning how the colder climate affects the grapes and sampling the latest vintages. You’ll also take a break for a tasty 2-course lunch, paired with wine, of course. A driver, lunch, all tastings souvenir wine glass and round-trip hotel transport are covered.
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Small group
  • 8 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD189.75 
From  
USD189.75 
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  • 8 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Reserve Now & Pay Later
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Chicago Underground Pedway Tour With Food, Chocolate & WineWine Tasting & Winery Tours

Chicago Underground Pedway Tour With Food, Chocolate & Wine

star-1
Discover the sights and flavors of Chicago on a 1.5- to 2-hour tour via the underground Pedway. The subterranean tour is the perfect way to explore the city without exposing yourself to the elements. Follow your guide to the Thompson Center, City Hall, and more. Along the way, whet your appetite with Garrett Mix popcorn, artisan sandwiches, and frozen kefir. The 4pm tour on Friday also includes a wine tasting.
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Booked by 8 travellers
  • 1 hour 30 minutes to 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD50.00 
From  
USD50.00 
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  • 1 hour 30 minutes to 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Third Coast Food and Farm TourDay Trips

SPECIAL OFFER

Third Coast Food and Farm Tour

Max Group Size: 8 guests + 1 guide. Please contact us for larger groups. Transport: Round-trip transportation from Downtown Chicago. Private tours include door to door pick up/drop off. Inclusions: • 5+ Food Tastings • 1+ Alcohol Tasting • Bottled Water & Soft Drinks • Digital Guidebook • Awesome Tour Guide!
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Small group
  • 5 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD140.00 
USD175.00
USD35.00 savings
From  
USD140.00 
USD175.00
USD35.00 savings
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  • 5 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Perfectly Paired Food and Wine TourDay Trips

SPECIAL OFFER

Perfectly Paired Food and Wine Tour

All the fun and deliciousness of our flagship Third Coast Food and Farm Tour with an oomph of something more! Wayward’s Perfectly Paired Tour shares Michigan’s best-kept secrets, taking the long way through the fields, orchards, and vineyards to the beaches and bays. From New Buffalo to Saugatuck along Michigan’s southern coast, we will explore the pure, natural goodness of F.L.O.S.S. (Fresh, Local, Organic, Seasonal, and Sustainable) offerings unique to Michigan, accompanied by the friendly smiles Midwesterner's are known for. HIGHLIGHTS:​
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Small group
  • 6 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD160.00 
USD200.00
USD40.00 savings
From  
USD160.00 
USD200.00
USD40.00 savings
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  • 6 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Third Coast Private TourDay Trips

SPECIAL OFFER

Third Coast Private Tour

Private tours are great for small groups including wedding and bridal parties, birthday parties, and reunions. Each tour is customizable from the date and starting time, to the activities, participating restaurant stops and more!
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Private experience
  • 6 to 7 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
USD1,120.00 
per group
USD1,400.00
USD280.00 savings
From  
USD1,120.00 
per group
USD1,400.00
USD280.00 savings
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  • 6 to 7 hours
  • Reserve Now & Pay Later
  • Free Cancellation


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