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Chicago skyline flight

Memorable views of an iconic city

When you visit Chicago, or if you want to fly between Wisconsin and Indiana without flying west of the city, consider a Chicago skyline flight. Chicago’s skyline comprises four of the nation’s 12 tallest buildings (the other eight are in New York City), the view of the city from above is breathtaking, and the route relatively easy to navigate. Here’s how.

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Illustration by Charles Floyd.
Alyssa J. Miller
Kollin Stagnito
Senior Vice President of Media
Senior Vice President of Media Kollin Stagnito is a commercial pilot, advanced and instrument ground instructor and a certificated remote pilot. He owns a 1953 Cessna 170B.

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