Introducing Chicago: Best Tours to Explore the Windy City

The best Chicago city tours take you from the dizzying heights of its skyline to the tranquility of its blue waterways 


Match your Chicago tour with your own interests, whether you're a foodie itching to chow down on deep dish pizza, or a history buff in search of sordid political tales. The Windy City's finest tours also offer an array of options for your adventure, including everything from bikes, boats and helicopters—to your own two feet.

Bobby's Bike Hike Chicago Tours

Who says you can't work out while on vacation? Bobby's Bike Hike Chicago Tours gives you the chance to burn some calories while soaking up the sights through its bike-themed tours. Enjoy panoramic views of the city as you pedal your way around the shores of Lake Michigan during the three-hour, 7-mile Lakefront Neighborhoods Bike Tour. Roll past enormous Gold Coast mansions, the North Side's buzzing beaches and the bustling Lincoln Park Zoo. Everything you need for your outdoor excursion is provided, including a bike, helmet and tour guide.

Chicago Architecture Foundation River Cruise

The Windy City's stunning skyline gets the attention it deserves with the Chicago Architecture Foundation River Cruise. Climb aboard a 200-seat riverboat and float down three arms of the Chicago River as a knowledgeable docent provides detailed history on more than 50 buildings. The 90-minute boat ride showcases structures found in such areas as Goose Island and River North. For a slightly altered perspective, the Twilight Tour launches as the sun sets over the skyline, while the Capture Chicago Photography Cruise pauses frequently to give shutterbugs the opportunity to take the perfect picture.

Chicago Elevated

Learn many of Chi-Town's best kept secrets when you take one of the uniquely themed tours offered by Chicago Elevated. The Chicago Pedway Tour, for instance, sends you on a journey along the city's extensive but little-known subterranean walkway system. The winter tour is not for the faint of heart, but it gives you the chance to experience Chicago's legendary cold weather. Tours are operated by an alumnus of Second City, Chicago's renowned improv troupe so, rest assured, you'll get a healthy dose of comedy on your expedition as well.

Chicago Helicopter Experience

Get a bird's eye view of the Windy City with the Chicago Helicopter Experience. The 15-minute adventure might be brief and pricey but it offers once-in-a-lifetime views of the skyline and Lake Michigan, as a pilot provides a narrated tour of the city's landmark attractions. Tours take place during the day, at twilight and in the evening. From Memorial to Labor Day weekend, you can also enjoy a unique vantage point of the Navy Pier's twice-weekly fireworks show. Make sure you also visit the expansive Chicago exhibit located inside the heliport.

Chicago Pizza Tours

Chicagoans will always unite for one common belief—the superiority of their pizza above all others! It's no surprise then that Chicago Pizza Tours offers some of the most popular pizza expeditions in town. Bring your appetite for the three-hour-plus Original Chicago Pizza Tour, where you'll sample an array of pies, including Chicago's traditional deep dish offering, from four local pizzerias. You'll also get a behind-the-scenes kitchen tour and hear from dough masters as they discuss the art of making pizza.

Frank Lloyd Wright Trust Tours

Walk in the footsteps of one of the greatest American architects with the Frank Lloyd Wright Trust Tours. Can't decide which of the many tours to take? The extensive seven-hour Wright Around Chicago Tour highlights his most iconic regional works, including the Robie House in Hyde Park and the Rookery, Wright's Loop-based skyscraper. The tour also ventures out to the suburb of Oak Park, 15 minutes west of Chicago, home to the largest collection of Wright buildings, including his one-time home and studio.


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