A host of enticing, unconventional Chicago tours goes beyond the typical Windy City institutions from Lake Shore Drive bike routes to major downtown museums. Those who visit Chicago—particularly those who only have a couple days in the city—want to see sites off the beaten path and not swarming with slow-moving pedestrians. Whether you’re a Chicago native who’s transformed into a tourist for a day or an out-of-towner curious about the city’s most colorful cultural attractions, you’re certain to find something here to keep you entertained.
Chicago Beer Experience Beer Tour
Designed for novices and connoisseurs alike, the Chicago Beer Experience beer-focused walking tour introduces participants to intriguing hot spots in either the Bucktown and Wicker Park or Lakeview and Lincoln Park neighborhoods. These quirky tours include a knowledgeable guide who offers little-known facts about the areas, and more importantly, beer. Also included in the tour are visits to four beer-oriented bars as well as beer tastings and a Chicago-style hot dog. Tours happen from 3:30-6:30 p.m. every Saturday and cost $59.90 per person or $33.90 with no beer tastings. You must be at least 21 to participate.
Chicago Blues City Tour
No local tour is complete without tunes and the Chicago Blues City Tour satisfies any dedicated music fan. This 90-minute luxury bus adventure showcases the most significant blues venues throughout the city. You jam to blues on the bus, then file into a number of well-known live-music spots and institutions, such as the famed Willie Dixon’s Blues Heaven Foundation. It occurs year-round at 3:30 p.m. daily, costs $30 per person, and is for all ages.
Chicago Food Planet Chinatown Food Tour
For one of the most remarkable walking-style Chicago tours, check out Chicago Food Planet Food Tour in Chinatown located just south of downtown. In between visits to some of the area’s most popular and authentic Chinese eateries, you see historical sites and cultural landmarks and indulge in Hong Kong-style dim sum, an authentic Peking duck dinner, Chinese pastries, and more. The three-and-a-half-hour tour is seasonal and runs Saturday through Monday, March through November. It costs $55 for adults and $35 for children under 12.
Slice of Chicago Pizza Tours
Is there more to Chicago pizza than deep dish? When you check out the Slice of Chicago Pizza Tour you find out as you travel to a number of favorite spots by foot in the downtown area. From the legendary Uno’s Pizzeria to the more contemporary Quartino Ristorante, these places treat you to slices along the route. The two-hour tours are seasonal and happen every Thursday through Sunday. They cost $50 per person and are appropriate for all ages.
Bobby’s Bike Hike Southside Gangster Tour
Skip the typical Chicago tours and bike routes and instead take a ride on the wild side with Bobby’s Bike Hike Southside Gangster Tour. This bike ride travels through the old Bridgeport neighborhood where you learn about the Chicago Outfit and Al Capone’s most infamous stomping grounds. The 13-mile, three-and-a-half-hour tour includes a bicycle and helmet in addition to a well-informed guide. It’s seasonal and kicks off at 9:30 a.m. Friday through Sunday. It costs $49.75 per person and $44.75 for students.