Empty Leg Flights from Chicago (MDW)
Empty leg flights to and from Chicago (MDW). Over the last 12 months we tracked 176 departing and 177 arriving repositioning legs across 12 active months. Most frequent destinations: TEB, PBI, APF, OPF. Aircraft commonly seen on these legs: Light Jet, Super Light Jet, Midsize.
Indicative pricing on tracked legs:
$2,688
– $66,747
· 353 legs over 12 months
No live empty legs are currently listed departing from MDW. Over the last 12 months this hub saw 176 departing repositioning legs — submit a search above and we will alert you when a matching leg opens up.
From:
Georgetown, Sussex County (GED), DE, US (GED)
Georgetown, Sussex County (GED), DE, US (GED)
To:
Chicago, Midway International (MDW), IL, US (MDW)
Chicago, Midway International (MDW), IL, US (MDW)
Departure date:
17.06.2026
17.06.2026
Aircraft:
Super Light Jet
Super Light Jet
Capacity:
9
9
$11,592
From:
Toronto, Lester B. Pearson International (YYZ), ON, CA (YYZ)
Toronto, Lester B. Pearson International (YYZ), ON, CA (YYZ)
To:
Chicago, Midway International (MDW), IL, US (MDW)
Chicago, Midway International (MDW), IL, US (MDW)
Departure date:
20.06.2026
20.06.2026
Aircraft:
Ultra Long Range
Ultra Long Range
Capacity:
14
14
$14,020
Most frequent destinations from MDW
MDW → TEB
19 legs / 12 mo
19 legs / 12 mo
MDW → PBI
8 legs / 12 mo
8 legs / 12 mo
MDW → APF
6 legs / 12 mo
6 legs / 12 mo
MDW → OPF
4 legs / 12 mo
4 legs / 12 mo
MDW → VNY
4 legs / 12 mo
4 legs / 12 mo
MDW → SRQ
4 legs / 12 mo
4 legs / 12 mo
Aircraft commonly seen on these legs: Light Jet, Super Light Jet, Midsize, Heavy Jet, Super Midsize
