There are many ways to experience Chicago, including by foot, bike, boat, bus, trolley, kayak or Segway. In an effort to keep you on the right path in your Windy City exploration, we've rounded up some top-rated Chicago tours: bike tours, walking tours, boat tours and more. These are, in our opinion, the best Chicago tours for discovering attractions, beautiful buildings, history and culture (not to mention Chicago's best restaurants, craft breweries and the lakefront). Embrace your inner tourist.
Top Chicago tours
Chicago Architecture Foundation River Cruise
This Chicago architecture tour is a must for entertaining family and friends from out of town or just orienting yourself to the city’s many architectural wonders. With a knowledgeable docent in tow, you'll cruise along the Chicago River from River City north to Goose Island, taking in stunning, unimpeded views of some of the city's most famous skyscrapers along the way. Reservations are strongly recommended. 112 E Wacker Dr (312-922-3432, architecture.org). $46–$49 per person plus tax.
Loop Interior Architecture and Pedway Walking Tour
After you've gotten an overview from the river, get inside some of those buildings with this two-hour walking tour. Making use of the Pedway, the tour is almost completely indoors, making it a good option for winter visitors (or stormy summer days). Guests share iPads loaded with historic photos, videos and archival maps for additional context. Reservations are required. (312-350-1131, chicagodetours.com). $26, kids under 18 $18.
Lakefront Neighborhoods Tour
If you need a crash course in why Chicago is so damn awesome, this bike tour of the Lakefront should do the trick. Within three hours, you'll see Gold Coast mansions, Lincoln Park Zoo, the old Playboy Mansion and North Avenue Beach. You'll bike approximately seven miles along the Lakefront Trail, admiring the breathtaking skyline sights. Ticket price includes bike, helmet and guide. Reservations are recommended. 540 N Lake Shore Dr (312-245-9300, bobbysbikehike.com). $42.50, students/seniors (65+) $37.50, kids under 12 $25.75, kids under 4 $13.50.
Chicago Helicopter Experience
No Chicago tour will take you higher than the Chicago Helicopter Experience, which offers aerial tours of the city's skyline. You'll board a chopper on the outskirts of Bridgeport and fly up the coast of Lake Michigan to Montrose Harbor and back in about 15 minutes. The cost of the flight might seem a little steep, but the photo opportunities are priceless. 2420 S Halsted St, (312-967-8687, chetours.com). $148–$178.
Chicago Brew Bus
There aren't many tours that you're encouraged to get trashed on, but this is one of them. Hop on the Brew Bus and travel to local breweries like Lagunitas, Atlas, Revolution and Lake Effect—yes, you can drink on the way. Each tour stops at three different breweries and includes four to six samples at each location. Reservations are recommended. (773-340-2739, chicagobrewbus.com). $79 per person.
Frank Lloyd Wright Tour
A visit to the Chicagoland area wouldn't be complete without a tour of the Frank Lloyd Wright Historic District in Oak Park, home to the world's largest collection of Wright-designed buildings, including the architect's own home and studio. You can take a self-guided walking tour, but for the full experience you'll want to spring for the Wright Around Oak Park tour, a three-hour walk that includes access to Wright's studio as well as visits to nine other buildings. Operates from April to October. Reservations are strongly recommended. 951 Chicago Ave, Oak Park, IL (312-994-4000, gowright.org). $60.
The Second City’s Neighborhood Tour
History and humor collide in this unique walking tour combining some of Chicago's best features: lovely neighborhoods (in this case, Old Town), great architecture and, last but not least, funny people. Beginning and ending at the Second City on North Wells Street, the tour winds its way through the shady streets of Old Town and past the old haunts of Second City alumni. No bored, monotone docents rattling off dry facts here. Led by Margaret Hicks (author of Chicago Comedy: A Fairly Serious History), this is a neighborhood tour that both entertains and informs. 1616 N Wells St (312-337-3992, secondcity.com). $18.
This Chicago-based startup is still in soft-launch mode, but the concept intrigues: The service connects you with “Xoobies,” its carefully screened local experts, for curated experiences like a scavenger hunt of Graceland Cemetery, a walking tour of the Loop focused on writers and literary characters or a guided excursion to sites of Chicago’s radio history. Locations and prices vary (xoobies.com).
Chicago Segway Tour
Just a heads up: This is not a tour for visitors to Chicago who want to "blend in" and "do what the locals do." Riding a Segway around the Loop with your friends and family is akin to tattooing "TOURIST" on your forehead. If you don't mind looking like a mall cop, it's way more fun than walking. You'll explore city landmarks, famous architecture and scenic spots along Lake Michigan. Reservations are required. 505 N Lakeshore Dr (312-890-3701, chicagosegwaytour.com). $45–$85.
Chicago Film Tour
Chicago has been the backdrop to many classic films and Hollywood blockbusters—from Ferris Bueller's Day Off to The Fugitive to The Dark Knight. This bus tour ventures all over the city to more than 30 locations where more than 80 movies were shot. You'll learn behind-the-scenes trivia, details of current filming activity in Chicago and more. It's a reel adventure. 600 N Clark St (312-593-4455, chicagofilmtour.com). $30.