One of the many great things about Chicago is that it is relatively easy to navigate as a visitor. The city is home to the nation’s second largest public transportation system, a network of elevated trains, subway lines and buses that can schlep you around the city or out to 35 surrounding suburbs. With a robust bike sharing system, known as Divvy, and the recently granted title of most bike-friendly city in the country by Bicycling Magazine, getting around via two wheels when the weather cooperates is another great option.
Arguably the best and easiest way to see the city, however, is one of the many unique guided tours that not only get you around Chicago, but do it with the added bonus of learning something along the way. The seven guided adventures in this gallery aren’t your average walking tours, although some do include walking, instead they’ll have you exploring the city’s architecture, history and craft beer scene via Segways, pedways, helicopters and even a giant barrel on wheels.
Going it alone and creating your own itinerary is truly a breeze, and while you don’t need to be savvy traveler or modern-day Magellan to reap the many wonders that a visit to the Second City has to offer. These seven tours grant you a unique perspective and fun approach to exploring Chicago.
Paste Travel’s Bucket List columnist Lauren Kilberg is a Chicago-based freelance writer. Her travels have found her camping near the Pakistani border of India and conquering volcanoes in the Philippines.
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You really can't visit Chicago without taking a river boat tour. A variety of operators offer plenty of options, but one of the most popular is by Wendella. They take you down all three branches of the Chicago River and by some of the city's best architecture. Top-notch guides narrate the tour with insights on "Chicago's legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire." Tickets are $35.50 for adults and the tour lasts for 75 minutes.
Photo by Camron Flanders, CC BY-NC-ND 2.0
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From Revolution to Lake Effect, Chicago has a thriving craft brewery scene and what better way to tour some of its best than in a giant Prohibition-style barrel. The aptly named Barrel Run Chicago Brewery Tour takes you to three tasting breweries and also includes a tour of one production facility. The breweries you'll visit depends on what tour you sign up for, but a good number of Chicago's best are in regular rotation and include Temperance, Lagunitas, Goose Island, Empirical, Revolution and Lake Effect. Tickets are $65 and tours last for around 4 hours.
Photo by The Barrel Run
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Most tours offer you a ground-level perspective of the city, but the Chicago Helicopter Experience takes you above Chicago for a bird's-eye-view of its iconic skyline. While more pricey than the other tours in this gallery, the unique view you'll get is hard to put a price on. Options include daytime, twilight and nighttime tours. If you'll be in Chicago between Memorial Day and Labor Day, don't miss the fireworks tour, which grants you aerial views of Chicago's Navy Pier fireworks show. Tours range from $148 to $178 and upwards.
Photo by Shutter Runner, CC BY-NC 2.0
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The Chicago Architecture Foundation "is the leading organization devoted to celebrating and promoting Chicago as a center of architectural innovation." In support of their mission to inspire people to "discover why design matters," CAF offers a variety of tours consistently considered among the city's best. The Must-See Chicago tour is a great crash course on why the city is known for its architecture and features some of Chicago's most famous built wonders like the Willis (Sears) Tower, Chicago Theatre and Wrigley Building. Tickets are $20 and the tour lasts for 90 minutes.
Photo by Hammerin Man, CC BY 2.0
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The Chicago pedway system snakes beneath a portion of the city and while frequently used by locals, it remains relatively unknown among visitors. The Chicago Architecture Foundation offers a Pedway Tour that takes you from the futuristic Thompson Center to the trippy Radisson Blu Aqua Hotel. Along the way you'll hear about the "history, design and unique surprises of the underground system" while finding "linkages to Chicago's major government and Loop office and residential structures." Tickets are $15 and the tour last for 120 minutes.
Photo by Chicago Architecture Foundation
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City Segway Tours offers a menu of options that all have you gliding around Chicago via Segway. Their tours take you by the city's most iconic sights, including Museum Campus, Buckingham Fountain, Soldier Field, Grant Park, as well as the lakefront for views of Lake Michigan and the skyline. While the mode of transportation is definitely a perk, their fun and informative guides are what make City Segway Tours great, rather than gimmicky. Along with their more conventional city tours, they also offer a Segway Poketour, which takes you "around areas in Chicago stocked with plenty of creatures, gyms and other goodies in record time."
Photo by City Segway Tours
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Chicago's past is famous for a few major events, including the World's Fair, Great Fire and Prohibition. With this in mind, it's only fitting that a Prohibition Tour makes this gallery. You'll travel to a handful of speakeasies scattered throughout the city while learning about the infamous era and its key players like Al Capone. Tours include stops at Marge's Still, the oldest continuously-running tavern in Chicago and Club Lucky.
Photo by Thomas Hawk, CC BY-NC 2.0