There are many ways to experience Chicago, including by foot, bike, boat, bus, trolley, kayak or Segway. You could also get around via horse and carriage or PedalPub, but those modes of transport are geared more toward newlyweds and college bros, respectively.
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, architectural tours and more. These are, in our opinion, the best Chicago tours for discovering Chicago attractions, architecture, history and culture…and food and off-the-beaten-path neighborhoods and the lakefront.
City Lights at Night Tour
Unlike vampires, Chicago doesn't suck at night. In fact, from certain vantage points, it looks pretty damn good. On the City Lights at Night tour, you'll pedal to various hotspots, including Millennium Park, the Museum Campus and Buckingham Fountain, with its world-famous light show. Wednesday and Saturday nights include the fireworks display at Navy Pier (Memorial Day through Labor Day). Ticket price includes bike, helmet and guide. Reservations are recommended. 312-915-0995, bobbysbikehike.com. $35, students/seniors (65+) $30, kids under 4 $10. Bus: 29, 65, 66, 124
Architecture River Cruises
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. 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. For a full list of Chicago Architecture Foundation tours, visit architecture.org. 312-922-3432. $37.85 per person plus tax. Subway: Brown, Green, Orange, Pink, Purple (rush hrs) to State/Lake
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. There are both 75–90-minute self-guided walking tours (in English, French, German, Italian, Japanese and Spanish) and 60–75-minute guided walking tours. 312-994-4000, gowright.org.
Chicago Cultural Center Tour
A volunteer Insta-Greeter shows you around the city's epicenter. 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. Reservations are not required. 312-744-6630, greeters.com. Subway: Red to Lake; Brown, Green, Orange, Pink, Purple (rush hrs) to Randolph
Good Times Historic Bar Tour
Described as a "mostly indoor pub crawl with an educational twist," this lively tour explores storied bars, stunning lobbies and historic buildings downtown. Guests learn about Prohibition, jazz, theater and social clubs; interact with historic photos and videos on shared iPads and make three drinks stops. (Appetizers and other extras are included; drinks are on you.) Since the tour is mostly indoors, there's not actually much walking (or stumbling, as the case may be). The tour begins at Argo Tea and ends near Rush and Ohio streets. 312-350-1131, chicagodetours.com. $34, students/seniors $32.
Want to see da Chicago of da Prohibition Era? When gangstas ruled da South Side? On this tour to 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. A bang-up time. Reservations recommended. 773-881-1195, gangstertour.com. $30. Subway: Red to Grand
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 tour ventures all over the city to more than 30 locations where more than 80 movies shot. You'll learn behind-the-scenes trivia, details of current filming activity in Chicago and more. It's a reel [sic] adventure. 312-593-4455, chicagofilmtour.com. $30.
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. That aside, it's way more fun than walking. You'll explore city landmarks, famous architecture and scenic spots along Lake Michigan. Reservations are required. 312-890-3701, chicagosegwaytour.com. $85.