5 Classic Movies That Make Us Want to Hop on a Flight to the Windy City

5 Classic Movies That Make Us Want to Hop on a Flight to the Windy City
Paramount/Courtesy of The Everett Collection
Intro Deck: 

From Humboldt Park’s recent surge of vintage shops to Wicker Park’s mind-blowing culinary scene and Grant Park’s 25 Years of Lollapalooza extravaganza this month, the lakefront metropolis of Chicago has never felt so dynamic. See everything we're loving about the Windy City right now.

We never really need an excuse to take a trip to the Windy City. Just the thought of a deep dish slice from Giordano’s or a few hours of shoe shopping in Ikram is well worth the price of airfare alone. But there are a handful of classic films that capture the city's spirit so perfectly, we’re practically digging out our weekend bags by the time the credits roll.

From Ferris Bueller's epic parade performance on Dearborn Street to My Best Friend’s Wedding’s tearjerker boat scene on the Chicago River, we’re looking back on some of our all-time favorite films that are unofficial love letters to the best of the Midwest. Because really, who hasn’t secretly wanted to run through O’Hare Airport like the McCallisters in Home Alone?

Shop This Post

Sponsored Stories


Must Reads

 
 
Back to Top