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
From:
Chicago, Midway International (MDW), IL, US (MDW)
Chicago, Midway International (MDW), IL, US (MDW)
To:
West Palm Beach, Palm Beach International (PBI), FL, US (PBI)
West Palm Beach, Palm Beach International (PBI), FL, US (PBI)
Departure date:
28.05.2026
28.05.2026
Aircraft:
Light Jet
Light Jet
Capacity:
7
7
$8,918
From:
Chicago, Midway International (MDW), IL, US (MDW)
Chicago, Midway International (MDW), IL, US (MDW)
To:
Jacksonville, Craig Municipal (CRG), FL, US (CRG)
Jacksonville, Craig Municipal (CRG), FL, US (CRG)
Departure date:
29.05.2026
29.05.2026
Aircraft:
Super Light Jet
Super Light Jet
Capacity:
7
7
$6,242
From:
Chicago, Midway International (MDW), IL, US (MDW)
Chicago, Midway International (MDW), IL, US (MDW)
To:
Teterboro, Teterboro Airport (TEB), NJ, US (TEB)
Teterboro, Teterboro Airport (TEB), NJ, US (TEB)
Departure date:
03.06.2026
03.06.2026
Aircraft:
Super Midsize
Super Midsize
Capacity:
8
8
$10,707
From:
Chicago, Midway International (MDW), IL, US (MDW)
Chicago, Midway International (MDW), IL, US (MDW)
To:
Teterboro, Teterboro Airport (TEB), NJ, US (TEB)
Teterboro, Teterboro Airport (TEB), NJ, US (TEB)
Departure date:
13.06.2026
13.06.2026
Aircraft:
Super Midsize
Super Midsize
Capacity:
9
9
$10,707
From:
Washington, Dulles International (IAD), DC, US (IAD)
Washington, Dulles International (IAD), DC, US (IAD)
To:
Chicago, Midway International (MDW), IL, US (MDW)
Chicago, Midway International (MDW), IL, US (MDW)
Departure date:
25.05.2026
25.05.2026
Aircraft:
Heavy Jet
Heavy Jet
Capacity:
14
14
$13,384
From:
Washington, Dulles International (IAD), DC, US (IAD)
Washington, Dulles International (IAD), DC, US (IAD)
To:
Chicago, Midway International (MDW), IL, US (MDW)
Chicago, Midway International (MDW), IL, US (MDW)
Departure date:
27.05.2026
27.05.2026
Aircraft:
Super Light Jet
Super Light Jet
Capacity:
8
8
$11,743
From:
Teterboro, Teterboro Airport (TEB), NJ, US (TEB)
Teterboro, Teterboro Airport (TEB), NJ, US (TEB)
To:
Chicago, Midway International (MDW), IL, US (MDW)
Chicago, Midway International (MDW), IL, US (MDW)
Departure date:
07.06.2026
07.06.2026
Aircraft:
Midsize
Midsize
Capacity:
6
6
$13,652
From:
Sacramento, Sacramento International Airport (SMF), CA, US (SMF)
Sacramento, Sacramento International Airport (SMF), CA, US (SMF)
To:
Chicago, Midway International (MDW), IL, US (MDW)
Chicago, Midway International (MDW), IL, US (MDW)
Departure date:
09.06.2026
09.06.2026
Aircraft:
Midsize
Midsize
Capacity:
6
6
$20,777
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
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
