Comedians such as Tina Fey, Amy Poehler and Chris Farley rank among the greatest in modern America, and an evening of humour in Chicago is likely to come from improv and sketch comedy.

The kings and queens of Chicago – names such as Tina Fey, Amy Poehler and Chris Farley among them – rank among some of the greatest comedic minds in modern America, earning its reputation for bleeding-edge comedy one guffaw at a time. An evening in Second City’s Old Town headquarters is one of the banner entertainment opportunities offered by a trip to Chicago.

This club is symbolized by John Belushi, who emerged from the suburbs in 1970 with a creative, manic, no-holds barred style. Belushi soon moved to the main stage, and then to Saturday Night Live. Second City's shows are sharp and biting commentaries on life, politics, love and anything else that falls in the crosshairs of their hard-hitting wit. Second City Etc houses a training company that often presents more risky work, as actors try to get noticed and make the main stage. Both theatres offer the city's best comedy value after the last show most nights, when the comics present free improv performances.

In no small part because of the influence of Second City, an evening of humour in Chicago is much more likely to come from improv and sketch comedy than stand-up. Chicago's famous comedic names and ensembles descend on stages around the city for the Chicago Improv Festival every spring. Recently the festival has included a College Improv Tournament, which draws from a national pool of aspiring coeds who face off in a tournament bracket.

The rapid-fire Neo-Futurists (5153 N Ashland Ave), whose long-running, brilliant Too Much Light Makes the Baby Go Blind: 30 Plays in 60 Minutes will leave you breathless. The hyper troupe makes a manic attempt to perform 30 plays in 60 minutes, and admission cost is quirkily-based on the throw of a dice. Also worth a look is Comedysportz (929 W Belmont Ave). The gimmick? Two improv teams compete with deadly seriousness to make you laugh hysterically. The audience benefits from this comic capitalism, and all the fun is G-rated.

While you are in town, do not miss iO (ImprovOlympic) in Wrigleyville (3541 N Clark St), which is credited with creating the long-form improv skits. The Olympic Committee forced this comic veteran to change the name to its initials in 2005, a suitably laughable development in a long career of chuckles. It launched the careers of Mike Myers and MTV's Andy Dick, along with a host of other well-known comics. Shows hinge entirely on audience suggestions, and each turn can run 40 minutes or longer. If you are thoroughly motivated by what you see, iO offers a range of courses on comedy to suit every budget.

The article 'Chicago’s cutting-edge comedy' was published in partnership with Lonely Planet.