Windy City Tour Company in Chicago

10 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.

Uncover Chicago's Geneva and St. Charles area, one sip at a time, visiting local wineries and making a pit stop for an epicurean lunch fit for the most discerning foodies.

Get up-close and personal with wines, beers and spirits on a private tour designed around your interests. Leave all the details up to a professional event planner so you can focus on the fun.

Spend the day exploring Chicago's local wine scene, visiting three wineries and enjoying a gourmet lunch.

Wander through a working distillery for a behind-the-scenes look at how your favorite spirits are made. Sip on plenty of samples along the way and fuel up on a hearty lunch bursting with flavor.

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 some of the finest craft brews in the city—as well as some of the city's best pizza. Spend the entire day touring local craft breweries, then stop to have a pie for dinner.

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.