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Top Illinois Wine Tasting & Winery Tours

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360 Chicago Observation Deck (formerly John Hancock Observatory) Admission with Prosecco

This admission ticket for two people gets you and a special someone access to 360 Chicago (John Hancock Observatory) plus a half bottle of Prosecco — a package that’s not available for purchase at the tower. After a quick elevator ride to the 94th floor of the Hancock Center, savor panoramic views over Chicago from 1,000 feet (304 meters) above the Magnificent Mile. Lift your glass in a toast to landmarks like Navy Pier, the Willis (Sears) Tower and Lake Michigan. With mobile tickets, simply scan your phone for direct entry into 360 Chicago.
  • Duration: 1 day
  • Free Cancellation
  • Duration: 1 day
  • Free Cancellation
From  
US$70.00
From  
US$70.00
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Duneland Wine Country with Gourmet Lunch

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.
  • Duration: 7 hours
  • Free Cancellation
  • Duration: 7 hours
  • Free Cancellation
From  
US$185.00
From  
US$185.00
See Details

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.
  • Duration: 6 hours
  • Free Cancellation
  • Duration: 6 hours
  • Free Cancellation
From  
US$159.00
From  
US$159.00
See Details

SW Michigan Wine Country with Gourmet Lunch

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.
  • Duration: 8 hours
  • Free Cancellation
  • Duration: 8 hours
  • Free Cancellation
From  
US$185.00
From  
US$185.00
See Details


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(888) 680-5731
(888) 680-5731