Empty Leg Flights / Chicago
Empty Leg Flights from Chicago
1 live departure from Chicago airports (KMDW, KORD, KPWK, KDPA), arranged by Villiers Jets.
Departing Chicago
1 flights
Carrington Jets is an independent advisory, not an air carrier. Flights are arranged by Villiers Jets and operated by licensed carriers. We earn a commission on completed bookings. Struck-through charter prices are our own estimates based on typical hourly rates for the aircraft category and flight time — not operator quotes.
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Get Chicago departures first
Empty-leg flights appear and sell within days — often hours. Tell us where you fly from and we'll send new departures that match.
Carrington Jets is an independent advisory, not an air carrier. Flights are arranged by Villiers Jets and operated by licensed carriers. We earn a commission on completed bookings. Struck-through charter prices are our own estimates based on typical hourly rates for the aircraft category and flight time — not operator quotes.
Flying private from Chicago
Chicago anchors Midwest private aviation, and its empty legs are disproportionately useful: the city is a natural midpoint for transcontinental repositioning, so coastal legs appear here that would otherwise overfly the region entirely.
Chicago private jet airports
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Chicago Midway KMDW
The closest jet-capable field to the Loop, with major FBO presence.
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Chicago Executive (Palwaukee) KPWK
The dedicated business aviation airport on the north side, convenient for the North Shore suburbs.
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DuPage KDPA
Serves the western suburbs with less congestion and lower fees.
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O'Hare International KORD
Private traffic via FBO, mostly heavy jets and international departures.
Typical routes and seasonality
New York and Teterboro legs are the most common, followed by Florida in winter and Aspen/Eagle in ski season. Texas and West Coast legs pass through on repositioning runs, often at aggressive prices.
New to empty legs? Start with what an empty leg flight is and how to actually catch one .