Windy City Tour Company in Chicago

9 Tours and Activities

Discover the little-known Midwestern counterpart to Napa and Sonoma, Southwest Michigan. Explore this less-travelled wine region, which boasts over 20 wineries just 90 minutes from downtown Chicago.

Get up-close and personal with Michigan wines on a private tour designed to be entertaining and informative. Leave all the details up to WCTC so you and your guests are safe and having fun.

Tour Chicago's West Loop for a guided adventure full of delicious wines. Sip on a variety of reds and whites as you learn about these tasty vintages, as well as the area you're exploring.

Discover the finest craft brews in the city and how perfectly they pair with some of the city's best pizza. Spend an evening touring local craft breweries and enjoy a pizza dinner along the way!

Get your kicks on Route 66 with a guided tour down 45 miles of the legendary American highway. See classic cars and historic architecture along the way, and enjoy lunch at Dell Rhea's.

Explore the lush greenery of Chicago by walking through its many parks and gardens. Experience the Green City to the fullest, uncovering the many hidden gems and thriving neighborhoods along the way.

Wine, beer and distilled spirits are all fair game on this private tour for eight or more guests. Learn all about the art of fermentation for all types of beverages—and sample the fruits of the distillers' labors at each stop.

Discover Chicago's Geneva and St. Charles area, one sip at a time. Visit local wineries and making a pit stop for lunch fit for the most discerning of foodies.

Explore the border of Chicago on a wine adventure amidst the Indiana Dunes at the south end of Lake Michigan. Depart Chicago, visit three wineries, enjoy lunch and return by dinner.