Empty Leg Flights from Chicago (MDW)

Empty leg flights to and from Chicago (MDW). Over the last 12 months we tracked 109 departing and 122 arriving repositioning legs across 12 active months. Most frequent destinations: TEB, PBI, EGE, BDL. Aircraft commonly seen on these legs: Light Jet, Super Light Jet, Midsize.

Indicative pricing on tracked legs: $3,781 – $66,747 · 231 legs over 12 months

Empty Legs from MDW
Empty Legs to MDW (2)

No live empty legs are currently listed departing from MDW. Over the last 12 months this hub saw 109 departing repositioning legs — submit a search above and we will alert you when a matching leg opens up.

From:
Naples, Municipal (APF), FL, US (APF)

To:
Chicago, Midway International (MDW), IL, US (MDW)

Departure date:
23.09.2026

Aircraft:
Super Light Jet

Capacity:
9

$15,112

From:
Minneapolis, St Paul International/Wold-Chamberlain (MSP), MN, US (MSP)

To:
Chicago, Midway International (MDW), IL, US (MDW)

Departure date:
26.09.2026

Aircraft:
Midsize

Capacity:
7

$11,011