Show Me Chicago: Tours to Help You See the City Up Close

At the Chicago Architecture Center, you can explore modern skyscrapers, historic downtown, Art Deco landmarks and more by foot, boat or bus. There are a whopping 85 tours to choose from, and each one covers a different niche. The most popular outing is the 90-minute river cruise, which provides insider knowledge on 50 structures along the Chicago River. One of the newest offerings in the tour lineup: a 90-minute stroll through Chinatown with stops at a Chinese bakery and a former Italian church.

Chicago Greeter Service 

The free Chicago Greeter program is an informative and fun way to explore the city under the wing of a local volunteer. Spontaneous? Take the InstaGreeter hour-long walk through downtown on Fridays, Saturdays and Sundays. A planner? Sign up at least 10 days in advance for the Greeter Visit, which lasts two to four hours and personalizes the neighborhood, language and theme of the tour.

Chicago Helicopter Experience

Even the tallest skyscrapers can’t give Windy City visitors the sweeping, above-it-all views from this thrilling helicopter ride. Tours are offered during the day and at twilight, when glass-encased skyscrapers reflect the sunset. Headphones and a microphone allow passengers to ask questions as the pilot-turned-tour-guide points out landmarks like Soldier Field and the Museum Campus during the 17-minute flight.

Chicago Pedway Tour

During the winter months, navigate a 1-mile urban labyrinth of tunnels, enclosed paths and bridges that connect more than 40 blocks of downtown. Free Tours By Foot conducts this 2-hour “name-your-own-price” tour that passes through signature structures such as The Wrigley Building, The Marina Towers and City Hall. Come hungry for some hidden gem foodie stops along the way.

Chicago Segway Tour

Glide along with entertaining guides as you catch pretty vistas of Lake Michigan and the Museum Campus during this 2-hour tour. There’s plenty of time for photo-ops as you stop to learn about the lions who guard The Art Institute of Chicago, the Route 66 history of Buckingham Fountain, and lesser-known attractions like Chicago’s lakefront vegetable garden.

Underground Donut Tour

Choose between two delicious itineraries on this carb-tastic experience. The Original Downtown Tour includes two miles of walking, just enough calorie-burning to make room for four favorite stops such as Do-Rite Donuts and Stan’s Donuts (you’ll also learn some intriguing local pastry history as you indulge). The newer Wicker Park Donut Tour also swings by four locales including Mindy’s Hot Chocolate, where doughnut samples are paired with their namesake beverage.