The Ultimate Chicago Movie Tour

We’ll get this out of the way: Chicago, the 2002 Renee Zellweger-Catherine Zeta-Jones Jazz Age musical, was shot in Toronto, Canada. (The betrayal!) Still, cinephiles can find some comfort in the fact that the Second City has served as the primary backdrop to plenty of movies. Here, a day trip through some of the city’s starring moments on the silver screen.

10 a.m. — Ferris Bueller’s Day Off, Art Institute of Chicago

The best Chicago movie of all time, or the best Chicago movie of all time? John Hughes’s classic ode to playing hooky was shot all over the city, but one of the best-known scenes had the three delinquents following around a school group at the city’s best art museum. Grab two friends (or willing strangers) for that iconic gallery pose.

1 p.m. — Dark Knight, Twin Anchors

One of the darker scenes in a very dark movie was shot at this old-school rib joint, where Two-Face—aka Harvey Dent, aka our collective childhood nightmare—shot Detective Wuertz. Pay tribute with the $17 half slab.

3 p.m. — Divergent, Willis Tower

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One of the less-dreadful Hunger Games rip-offs, Divergent—set in post-apocalyptic Chicago—features the Sears Willis Tower as “The Hub,” the city center where the children are sorted into their life-determining factions. You can pay a bunch of money to go up to the observation deck, but the employees up there definitely frown upon any Dauntless-level building scaling.

4 p.m. — My Best Friend’s Wedding, Union Station

In love with your best friend? Need to confess your feelings before it’s too late? Union Station set the stage for Julia Roberts and Dermot Mulroney in this 1997 rom-com-dram gem—the dramatic arched ceilings and pew-like seats are perfect for cinematic declarations.  

6 p.m. — Blues Brothers, Wrigley Field

This 1980 cult classic memorably saw the Illinois Nazis chase John Belushi and Dan Ackroyd to 1060 West Addison, aka the home of the Cubs. Catch an evening game at one of baseball’s most historic stadiums (fedora neither included nor recommended).

9 p.m. — Drinking Buddies, Revolution Brewing

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This understated, overlooked flick is set in Avondale’s Revolution Brewery, an industrial taproom that makes killer America-themed ales. Try the Freedom of Speach sour and keep an eye out for a plaid-shirted hipster to fall boozily in love with.