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 food, the best bars in Bridgeport and the lakefront). Embrace your inner tourist.
RECOMMENDED: Find more to explore on the best Chicago tours
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 Drive (312-922-3432, architecture.org). $39.74–$42.58 per person plus tax.
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). $60.99 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–October. Reservations are strongly recommended. 951 Chicago Ave, Oak Park, IL (312-994-4000, gowright.org). $60.
Lakefront Neighborhoods Tour
If you need to 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). $38.75, students/seniors (65+) $33.75, kids under 12 $23.75, kids under 4 $13.
Big Shoulders Historic Bar and Food Tour
Big This lively tour explores storied bars and Chicago cuisine (hot dogs and tamales) in Bridgeport. Guests learn about the working class neightborhood, visit the home of the White Sox, view street murals, eat a chili-covered tamale and make three drinks stops. (Food and three servings of beer are included.) The three hour tour includes bus transportation between locations, so there's not much walking involved (or stumbling, as the case may be). Reservations are required. (312-350-1131, chicagodetours.com). Starting at $72 per person.
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.
Here's an offer you can't refuse: A tour that focuses on Prohibition Era Chicago, when gangsters ruled much of the city. On this bus tour of ol' hoodlum haunts, gambling dens, shootouts and brothels, costumed gangster guides tell you true stories of such legends as Dion O'Bannion, Johnny Torrio, Machine Gun Jack McGurn and John Dillinger. It's a bang-up time. Reservations recommended. 600 N Clark St (773-881-1195, gangstertour.com). $30.
Chicago Cultural Center Tour
A volunteer docent shows you around the city's epicenter on this free tour of the Chicago Cultural Center. Try to remain focused. If the plethora of performances, exhibits and public programs don't catch your eye, then the view of Preston Bradley Hall's mesmerizing Tiffany Dome just might. Public tours are presented Wednesdays, Thursdays, Fridays and Saturdays at 1:15pm. Private tours can be reserved Mondays though Fridays, 9 am-3 pm. 78 E Washington St (312-744-6630, cityofchicago.org). Free.
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.