Empty leg flights from Chicago Midway International Airport (MDW)
Updated Sep 15, 7 PM CDT · 20 legs posted in the last 7 days · 33 expired
7 empty legs are leaving Chicago Midway International Airport (MDW) right now and 4 flights are arriving, listed by the operators flying them and refreshed through the day. Chicago Midway International Airport serves Chicago alongside Chicago Executive Airport (PWK). Every price is an estimated total; one final price is confirmed with you before you book.
Departing Chicago Midway International Airport
Soonest first. Every row opens the full listing.
Arriving at Chicago Midway International Airport
Legs ending at MDW, soonest first.
Not the dates you need?
We email you as soon as another MDW empty leg posts.
Questions about Chicago Midway International Airport empty legs
- Which city does Chicago Midway International Airport (MDW) serve?
Chicago Midway International Airport is a Chicago airport, and every leg on this page departs or arrives at MDW. Empty legs touching Chicago also use Chicago Executive Airport (PWK); every Chicago leg, whichever field it uses, is at flyupleg.com/empty-legs/chicago.
- How many empty legs use MDW today?
7 empty legs are leaving MDW and 4 are arriving, listed by the operators flying them and refreshed through the day. Legs post and disappear daily, so the count changes.
- What does an empty leg from MDW cost?
Today's 11 legs at MDW are estimated at $3,750 to $19,500 for the whole aircraft, with estimates marked on each listing. Every price on the board is an estimated range. When you request a leg we confirm it with the operator and you get one final price before you book. You pay once, to the operator or to UpLeg; your quote says which.
- What happens if the operator cancels the empty leg?
Operators occasionally reschedule or cancel. Whatever you paid the operator is refunded under their terms, and we help you chase it. Anything you paid UpLeg is refunded in full. Set a free alert at flyupleg.com/alerts?from=KMDW and we email you the moment a matching leg posts.
How empty legs from Chicago Midway International Airport work
An empty leg out of Chicago Midway International Airport is a repositioning flight. A jet that finished a job at MDW has to get to its next one, or back to base, and the operator would rather sell the flight than fly the cabin empty. The price is for the whole aircraft, not per seat, and it is a fraction of a normal charter for the same aircraft and crew.
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 with a date and no time means the departure is not fixed yet; you settle it with the operator when you request. Private jets use Chicago's other fields too, so a leg that fits may be a short drive from MDW.
You request a leg, we confirm one final price with the operator before you agree to anything, and you pay once, to the operator or to UpLeg; your quote says which. There is no membership, no deposit to ask and no card on file. Fixed dates or a round trip are a charter: ask for a quote and we come back with one total for the whole aircraft.
More in the FAQ, or read how UpLeg works.