Empty legs

Chicago

Live empty leg flights to and from Chicago, straight from the charter operators that fly them.

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Not a broker

We list what operators publish and take no commission. Your enquiry goes to them.

Updated three times a day

Availability is re-read from operator sources through the day, and each leg carries its timestamp.

Prices as published

The figure shown is the operator's own, for the whole aircraft. Where none is published we say so.

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Empty leg flights from Chicago

Chicago is the corporate centre of the American Midwest and it has business aviation spread across half a dozen fields rather than concentrated in one. The empty leg flights here are corporate repositioning, which means they appear all year rather than seasonally.

The board shows twenty-two of twenty-six legs leaving, and the destinations are warm: Miami most often, then Charlevoix, Fort Lauderdale and Las Vegas. Thirteen different aircraft types across twenty-six legs is a wide fleet.

The airports

Chicago Executive and DuPage are usually faster end to end than O'Hare even though they are further from downtown, because the ground time is a fraction of it.

What an empty leg from Chicago costs

Where an operator publishes a price it is shown exactly as listed, as a whole-aircraft figure rather than a per-seat fare. Where none is published the card says so rather than estimating.

Midwest sectors are one to two hours; the runs to Florida and the west coast are three to four. You can also browse the whole list by aircraft type.

Chicago empty legs, by the numbers

Between 31 July and 27 August 2026 we recorded 26 empty leg flights touching Chicago: 22 departing, 4 arriving, across 16 partner airports. The airports that came up most were Miami (4), Charlevoix (2), Fort Lauderdale (2), Las Vegas (2). 13 different aircraft types appeared, most often the Citation CJ4 (4), the Falcon 900EX EASy (4), the Citation XLS (3).

Twenty-two of twenty-six were leaving, and Miami and Fort Lauderdale are both in the top four. Chicago's empty legs point south, which will surprise nobody who has been there in February.

These are counts from our own board over that window, so they reflect the operators we read rather than the whole market, and they are a record of what was listed, not a forecast. New legs appear with days of notice, which is what the route alert is for.

What to know before you enquire

An empty leg exists because of the paid charter around it, so it can be sold or moved without notice. Every listing here is recorded from what the operator published, with the date we last saw it. Treat it as a strong indication rather than a guarantee, and confirm with the operator before planning around it.

Empty Leg List is a listing service. We are not a broker, not an operator, and not party to any booking, and we take no commission. Your enquiry goes to the operator covering the route, who confirms availability and final price with you directly. If nothing matches, set a route alert and we email you when a leg on that corridor is listed.

Where these flights go

Working out the busiest corridors…

What flies here

Working out which aircraft show up…

Where the aircraft actually go

Other cities on the list

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