Chicago is an outstanding city. There is so much to do and see that even the locals find it challenging to keep up. For visiting tourists, sightseeing options—museums, architecture, iconic film locations, public art, parks—can be overwhelming. You could try to conquer them all with your own DIY itinerary, but with so many attractions, a structured tour may be a better choice. Depending upon your energy level—and the weather—options abound. Walking tours are, of course, one option; bike tours are another. But the latest iteration of the guided tour in Chicago is by Segway. These open air tours offer friction with maximum sights and landmarks minus the ambulatory exertion. If architecture is your passion, you can discover the city’s edificies from the incredible vantage point of the Chicago River. Then there are quirky tours that focus on film landmarks, mafia lore, and underground pedways. Read on for my favorites.
Margaret Hicks, a former Second City performer, does her tours a little differently. Her comedy-laced sightseeing experiences are informative, quirky, and inexpensive. The Binocular Tour showcases high-up art. The Pedway Tour uncovers Chicago’s underground pedestrian tunnel system. And The Loop Tour explores public art and architecture. All tours are 90 minutes and cost $20 per person.
Wright Around Chicago—Frank Lloyd Wright Trust Tour
The grand-daddy of modern architecture, Frank Lloyd Wright is a Chicago icon. This all-day guided bus tour includes visits to celebrated buildings like Robie House in Hyde Park and The Rookery in downtown Chicago, and also ventures into the Oak Park suburb to discover the architect’s home, studio, and Prairie School masterpiece Unity Temple.
Explore Chicago: Hop On, Hop Off Trolley Tour
A three-day pass allows you to curate your sightseeing experience by hopping on and off a trolley as you wish. Visit Chicago’s most famous attractions—The Art Institute, Navy Pier, the Field Museum, The John Hancock Building—and hop off whenever you want to enter the site, shop, or grab a snack.
City Segway Tours
Walking tours can be tiring, and bus tours can feel disconnected. The Segway experience combines the best of both worlds. This 2-3 hour guided tour features stops (note: you don’t enter the attractions) at the Field Museum, the Adler Planetarium, Grant Park, Millennium Park, and Soldier Field. Reservations are required, and the maximum party size is 8 people.
Chicago Architecture Foundation Boat Tour on Chicago’s First Lady
Bold architecture is one of the defining features of the city of Chicago, and discovering these buildings by boat is incredible. Filled with narrative about the city, this 90-minute cruise along the Chicago River is led by certified docents. Over the course of the tour, you’ll explore three branches of the river and view more than 50 sites.