06/12/2012 10:44 am ET Updated Jun 12, 2012

'Conan' In Chicago: 10-Foot Bratwurst Launched Across State Street Bridge (VIDEO)

Late-night host Conan O'Brien kicked off his one-week residency in Chicago in grand fashion Monday evening as he launched a 10-foot sausage across the State Street bridge and sailed through a "Chicago citizenship test" administered by Mayor Rahm Emanuel.

"With the permission of the Chicago Transit Authority, Chicago Police Department, Chicago marine police, Chicago Fire Department and a lot of people who just seem to like watching stuff jump and crash, … every night this week we'll be launching things over the State Street drawbridge," O'Brien pronounced Monday during the Chicago Theatre taping.

Did the 10-foot bratwurst-on-wheels successfully make the 80-foot jump across the bridge? Watch above to find out.

Later in the taping, Mayor Emanuel came on stage to test O'Brien's knowledge of his home for the next week.

The test started with 101-level questions about Chicago's nickname and the former name of the Willis Tower and got trickier (and funnier) from there:

Emanuel: "Why did Al Capone come from New York City to Chicago?"

O'Brien: "To study improv."

Emanuel: "What is the windiest place in Chicago?"

O'Brien: "The men's room at Giordano's."

(Watch the full segment below.)

"30 Rock" star and Second City alum Jack McBrayer also appeared on Monday's episode and touched on the seven years the Georgia native spent living in the city at the start of his comedy career.

Though the lottery for free tickets to attend the O'Brien tapings in Chicago has already come and gone, standby tickets are still available. The show will tape three more episodes through Thursday evening here as part of the Just For Laughs Chicago festival.

If you can't make it to the tapings, but still want a piece of memorabilia from O'Brien's Chicago week, 10 pop-up vending machines throughout the city's downtown area are offering up 6,000 free, limited-edition Team Coco t-shirts. All you'll need to get them is a "magic code" displayed during the episodes.

WATCH Mayor Emanuel quiz O'Brien about Chicago: