New York to Chicago empty leg flights
6 empty legs are flying New York to Chicago right now, listed by the operators flying them and refreshed through the day. Today's legs are light, mid and heavy cabins. Today's legs leave from Teterboro Airport (TEB), Long Island MacArthur Airport (ISP) and Morristown Municipal Airport (MMU) and land at Chicago Midway International Airport (MDW), Chicago Executive Airport (PWK) and Dupage Airport (DPA). Prices marked Estimated are ours; the rest are the operator's own.
Flying New York to Chicago
Soonest first. Every row opens the full listing.
Chicago to New York
The return direction, soonest first.
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How empty legs from New York to Chicago work
An empty leg from New York to Chicago is a repositioning flight. A jet that finished a job in New York has to get to Chicago for its next one, or back to base, and the operator would rather sell the seats than fly the cabin empty. That is why the price is a fraction of a normal charter for the same aircraft, same crew, same operator.
The date is set by the aircraft's schedule, not yours, and it can move or be withdrawn when the operator's plans change. A listing that shows a date with no time means the departure is not fixed yet; you settle it with the operator when you request. Legs appear anywhere from weeks to a day ahead.
UpLeg lists these legs free of charge. You request one, we confirm availability and price with the operator, and you pay the operator directly. There is no markup, no membership and no card on file.
More in the FAQ, or read how UpLeg works.