CHICAGO PAPER AIRPLANE
LIVE · WHEELS UP

Chicago, IL · est. 2025

PICK YOUR HEAD UP.

Chicago's masked paper airplane pilot. 258,000 strong. Launching folded fighters from altitudes you wouldn't believe — and rooftops you can't get to.

Flight Log Follow the Squad

AS SEEN IN: CHICAGO READER · NEWSWEEK · THE NERD STASH  ·  SORTIES FLOWN: 100+  ·  PLANES RETRIEVED: ≈ MOST OF THEM  ·  NEXT TARGET: WILLIS TOWER

258K+

Followers

100+

Launch Sites

1:42

Record Flight

1

Mystery Man

Dossier / 01

The Pilot,
identified only
by altitude.

He arrived in Chicago seven months out of Michigan State — logistics job, South Loop apartment, Post-it note on a slow workday. The first plane caught an updraft he didn't know existed. It also caught the internet.

Now the mask goes on before the window opens. Classic rock cues up. A paper jet rides a thermal past the Chicago River, across four blocks, and into someone's Tuesday. Fans DM launch-site tips. Brands DM contracts. The doorman nods on the way back up.

"Awe and wonder can be hard to come by when adulting sucks, the world is on fire, and our city's challenges are daunting." — Chicago Reader, Best of Chicago 2025

Flight Log / Redacted Excerpts

Legendary
Drops.

A sample from the hangar. The full archive stays with the pilot — and with the select few who book a briefing.

OP. 100 SHAMROCK

viral

St. Paddy's 100-Plane Drop

One hundred kelly-green fighters deployed from 345 N LaSalle to the tune of Dropkick Murphys. The city looked up. Briefly, the city was nine years old again.

Date
03.18.26
Altitude
≈ 420 ft AGL
Status
logged

OP. LONG SHOT

record

1:42 Record Flight

Thermals, tailwind, and a post-it with perfect creases. Current personal best for continuous flight — across four city blocks, never under 300 feet.

Date
classified
Altitude
≈ 520 ft AGL
Status
logged

OP. [REDACTED]

off-menu

Rooftop Launch — Location Withheld

A government building. No fence climbed, no doors kicked. Just a hallway, a service elevator, and a window nobody locked. The footage doesn't leave this hangar.

Date
pending release
Altitude
classified
Status
classified

OP. FACE-REVEAL

coming

500K Countdown

At 500,000 followers, the mask comes off. Atop Willis Tower. One plane, one pilot, one city. Sponsorship slots open until the counter hits.

Date
ETA 2026
Altitude
1,451 ft AGL
Status
pending

Some entries have been redacted for operational security. Booked partners receive unredacted briefings.

As seen in

Covered by the city. Quoted by the rest.

Chicago Reader

Best of Chicago 2025
"Pick your head up and you might see a plane," says this Chicago oracle.

Newsweek

Paper Plane With Handwritten Note Lands on Stranger's Balcony

The Nerd Stash

Masked Man Throws 100 Airplanes Off a Building in Illinois

Ops / Partnerships

Sponsorships.
Stunts. Stadium drops.
Let's fly.

If your brand, broadcast, or rooftop is ready for a spectacle — the pilot is booking. Lead times are short. Airspace is shorter.

Book the Pilot