5 Tours to Try in Chicago

In a city of more than 2.7 million people, 7,000-plus restaurants, 600 parks and 70 museums, it can be hard to know where to start exploring. A tour that aligns with your personal interests—architecture, food, art, biking—might be the perfect way to discover the Midwest's largest city.

Frank Lloyd Wright Trail

A self-guided trail connects 13 Frank Lloyd Wright properties in locations such as Chicago, Rockford and Springfield. After touring the stops in the Chicago area, including the Wright Home and Studio and the Frederick C. Robie House, head out to catch some of the others. The 35-room Dana-Thomas House in Springfield contains the nation's largest collection of Wright's site-specific original art glass and furniture; in Rockford, the Laurent House was designed for an owner with special access needs. Downloadable PDF files provide insight from architecture experts.

Pizza Tours That Go Deeper Than Deep Dish

Why just eat Chicago's world-famous pizza when you can also talk about it with knowledgeable "Doughcents"? Step aboard the Chicago Pizza Bus, or take a guided walk through a neighborhood, with Pizza City USA tours. Your experience might include kitchen tours, in-depth pizza analysis, and samples of deep-dish, Roman al Taglio, Neapolitan or Sicilian pizza. Owner/founder Steve Dolinsky—winner of 13 James Beard Foundation awards for his TV, radio and podcast work, and currently a food reporter for The Food Guy on Chicago's NBC 5—leads some of the tours himself (and personally trains the other guides).

Bike Your Way—Scenic or Spooky

Scenery, history and exercise! Hop on an electric-powered or classic bike and join the Bobby's Bike Hike guides in a casual pedal around town. Themes for the tours change periodically, but typically include a neighborhood excursion, top attractions tour and food tour. Make reservations early for the Bobby's Fright Hike: Halloween Edition Night Bike Tour in October—three hours of pedaling through some of the city's spookiest spots.

Art with Sass at the Art Institute of Chicago

Museum Hack's tours of the Art Institute of Chicago are as funny as they are informative. Behind-the-scenes looks at the museum include stories about art and artists (spiced with sarcasm and jokes), games (with prizes!) and fun photo ops. You can customize your tour with a theme such as Game of Thrones or 19th Century French Impressionism.

Design and History with Chicago Architecture Foundation

The Chicago Architecture Foundation, which runs Chicago's most extensive tours, became its own destination in 2018, when the Chicago Architecture Center opened at 111 E. Wacker Drive. Chicago City Model Experience tells the story of the city's role in architecture, with 4,000 model buildings, a film and interactive light show; Reframed: The Future of Cities in Wood (through October 2023) explores the promise of sustainably sourced wood. Also at the center: Buy tickets for city tours like the popular river excursion aboard Chicago's First Lady.