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  5. From Chicago

Empty Leg Flights From Chicago — 147 Live

147 live empty leg flights departing from Chicago metro on SkyAccess, sourced from FAA Part 135 charter operators repositioning aircraft through Chicago Executive (KPWK) and the 80-mile radius around it. Empty legs are priced 25–80% below retail charter, with the deepest discounts in the 24–72 hour window before departure.

View arrivals to ChicagoSearch all empty legs

Departing from Chicago (24 of 147)

  • Sun, Jun 14
    (KDPA) Chicago, Illinois, United States→(KGRR) Grand Rapids, Michigan, United States
    Hawker 850XP
    $3,498
  • Sun, Jun 14
    (KGYY) Gary, Indiana, United States→(KPDC) Prairie Du Chien, Wisconsin, United States
Beechcraft Hawker 900XP
$6,145
  • Sun, Jun 14
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport→(KIMT) Iron Mountain / Kingsford, Michigan, United States - Ford Airport
    Cessna Citation XLS+
    $4,923
  • Sun, Jun 14
    (KENW) Kenosha, Wisconsin, United States→(KGYY) Gary, Indiana, United States
    Bombardier Challenger 350
    $4,176
  • Sun, Jun 14
    (KMDW) Chicago, Illinois, United States→(KPBI) West Palm Beach, Florida, United States
    Cessna Citation CJ3
    $9,772
  • Sun, Jun 14
    (KMDW) Chicago, Illinois, United States→(KBNA) Nashville, Tennessee, United States
    Embraer Legacy 600
    $10,908
  • Sun, Jun 14
    (KDPA) Chicago, Illinois, United States→(KORL) Orlando, Florida, United States
    Bombardier Learjet 60
    $16,884
  • Sun, Jun 14
    (KARR) Chicago, Illinois, United States→(KIND) Indianapolis, Indiana, United States
    Dassault Falcon 50EX
    $4,761
  • Sun, Jun 14
    (KUES) Waukesha, Wisconsin, United States→(KELM) Elmira/Corning, New York, United States
    Cessna Citation CJ4
    $9,380
  • Sun, Jun 14
    (KDPA) Chicago/West Chicago, Illinois, United States - Dupage Airport→(KBHM) Birmingham, Alabama, United States - Birmingham-Shuttlesworth International Airport
    Bombardier Learjet 60
    $10,130
  • Mon, Jun 15
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport→(KOPF) Miami, Florida, United States - Miami-Opa Locka Executive Airport
    Gulfstream IV
    $17,565
  • Mon, Jun 15
    (KDPA) Chicago, Illinois, United States→(KHPN) White Plains, New York, United States
    Gulfstream G IV SP
    $26,800
  • Mon, Jun 15
    (KUES) Waukesha, Wisconsin, United States→(KTEB) Teterboro, New Jersey, United States
    Cessna Citation CJ4
    $9,380
  • Mon, Jun 15
    (KMKE) Milwaukee, Wisconsin, United States→(KCSG) Columbus, Georgia, United States
    Cessna Citation CJ4
    $9,380
  • Mon, Jun 15
    (KRFD) Chicago, Illinois, United States→(KMKE) Milwaukee, Wisconsin, United States
    Beechcraft Hawker 800XP
    $12,060
  • Mon, Jun 15
    (KDPA) Chicago, Illinois, United States→(KFSD) Sioux Falls, South Dakota, United States
    Cessna Citation Excel
    $10,921
  • Mon, Jun 15
    (KMDW) Chicago, Illinois, United States→(CYHM) Hamilton, Canada
    Gulfstream G150
    $4,482
  • Mon, Jun 15
    (KMDW) Chicago, Illinois, United States→(KGRR) Grand Rapids, Michigan, United States
    Cessna Citation XLS
    $7,035
  • Tue, Jun 16
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport→(CYYZ) Toronto, Ontario, Canada - Lester B. Pearson International Airport (Mississauga)
    Bombardier Challenger 300
    $7,418
  • Tue, Jun 16
    (KGYY) Gary, Indiana, United States→(KFSD) Sioux Falls, South Dakota, United States
    Honda Aircraft HA-420 HondaJet
    $4,678
  • Tue, Jun 16
    (KJVL) Janesville, Wisconsin, United States→(KFTY) Atlanta, Georgia, United States
    Bombardier Challenger 300
    $11,292
  • Tue, Jun 16
    (KMKE) Milwaukee, Wisconsin, United States→(KBCT) Boca Raton, Florida, United States
    Cessna Citation CJ4
    $14,238
  • Tue, Jun 16
    (KMDW) Chicago, Illinois, United States→(KLNK) Lincoln, Nebraska, United States
    Cessna CitationJet
    $4,690
  • Tue, Jun 16
    (KGYY) Gary, Indiana, United States - Gary Chicago International Airport→(KFSD) Sioux Falls, South Dakota, United States - Joe Foss Field Airport
    Honda Aircraft HA-420 HondaJet
    $5,563

    • Frequently asked about Chicago empty legs

    How many empty leg flights are available from Chicago?
    147 live empty leg flights departing from Chicago today on SkyAccess, sourced from FAA Part 135 charter operators repositioning aircraft through the Chicago metro cluster. Inventory updates hourly.
    What airports serve Chicago empty leg flights?
    Primary GA airport: Chicago Executive (KPWK). SkyAccess searches a 80-mile radius around the primary airport to catch every charter-friendly field in the Chicago metro cluster — so this page surfaces empty legs from all IL GA airports within range.
    How much can I save flying empty leg from Chicago?
    Typical empty leg pricing from Chicago runs 25–80% below the equivalent retail charter rate. Discounts deepen as departure approaches: same-day legs commonly clear at 70–80% off retail, while 14-day-out inventory is closer to 35–40% off.
    When should I book an empty leg from Chicago?
    For the deepest discount, search within 24–72 hours of departure. Inventory peaks Wednesday through Friday on most IL corridors. Set saved-search alerts on the KPWK radius to catch new listings as they publish.