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  5. From Chicago

Empty Leg Flights From Chicago — 97 Live

97 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 97)

  • Wed, Jul 8
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport→(KHPN) White Plains, New York, United States - Westchester County Airport
    Bombardier Learjet 60
    $13,025
  • Thu, Jul 9
    (KMDW) Chicago, Illinois, United States→(KBNA) Nashville, Tennessee, United States
Cessna Citation II
$7,057
  • Thu, Jul 9
    (KPWK) Chicago, Illinois, United States→(KHYR) Hayward, Wisconsin, United States
    Bombardier Learjet 45
    $9,782
  • Thu, Jul 9
    (KJVL) Janesville, Wisconsin, United States - Southern Wisconsin Regional Airport→(KPLN) Pellston, Michigan, United States - Pellston Regional Airport of Emmet County Airport
    Beechcraft Hawker 850XP
    $5,024
  • Thu, Jul 9
    (KDPA) Chicago, Illinois, United States→(EHAM) Amsterdam, Netherlands
    Dassault Falcon 8X
    $114,139
  • Thu, Jul 9
    (KMDW) Chicago, Illinois, United States→(KARR) Chicago, Illinois, United States
    Dassault Falcon 50EX
    $7,370
  • Thu, Jul 9
    (KENW) Kenosha, Wisconsin, United States→(KFCI) North Chesterfield, Virginia, United States
    Beechcraft Hawker 900XP
    $8,825
  • Fri, Jul 10
    (KORD) Chicago, Illinois, United States - Chicago O'Hare International Airport→(KGRR) Grand Rapids, Michigan, United States - Gerald R. Ford International Airport
    Cessna Citation Excel
    $3,075
  • Fri, Jul 10
    (KMKE) Milwaukee, Wisconsin, United States→(KFCM) Minneapolis, Minnesota, United States
    Cessna Citation CJ4
    $9,380
  • Sat, Jul 11
    (KMKE) Milwaukee, Wisconsin, United States→(KASE) Aspen, Colorado, United States
    Cessna Citation CJ4
    $13,366
  • Sat, Jul 11
    (KORD) Chicago, Illinois, United States→(KGYY) Gary, Indiana, United States
    Honda Aircraft HA-420 HondaJet
    $3,637
  • Sun, Jul 12
    (KDPA) Chicago, Illinois, United States→(KDTW) Detroit, Michigan, United States
    Gulfstream G500
    $14,673
  • Sun, Jul 12
    (KMKE) Milwaukee, Wisconsin, United States→(KASE) Aspen, Colorado, United States
    Cessna Citation CJ4
    $13,366
  • Sun, Jul 12
    (KPWK) Chicago, Illinois, United States→(KCVG) Cincinnati / Covington, Kentucky, United States
    Cessna Citation CJ3+
    $4,221
  • Sun, Jul 12
    (KMKE) Milwaukee, Wisconsin, United States→(KCRQ) Carlsbad, California, United States
    Cessna Citation CJ4
    $21,386
  • Sun, Jul 12
    (KARR) Chicago, Illinois, United States→(KMDW) Chicago, Illinois, United States
    Dassault Falcon 50EX
    $7,420
  • Sun, Jul 12
    (KARR) Chicago, Illinois, United States→(KPLN) Pellston, Michigan, United States
    Dassault Falcon 900
    $6,948
  • Sun, Jul 12
    (KJVL) Janesville, Wisconsin, United States - Southern Wisconsin Regional Airport→(KTVC) Traverse City, Michigan, United States - Cherry Capital Airport
    Beechcraft Hawker 850XP
    $4,306
  • Sun, Jul 12
    (KMKE) Milwaukee, Wisconsin, United States→(KLBF) North Platte, Nebraska, United States
    Cessna Citation CJ4
    $9,402
  • Sun, Jul 12
    (KMDW) Chicago, Illinois, United States - Chicago Midway International Airport→(KMSP) Minneapolis, Minnesota, United States - Minneapolis-St Paul International/Wold-Chamberlain Airport
    Bombardier Learjet 60
    $8,308
  • Sun, Jul 12
    (KMKE) Milwaukee, Wisconsin, United States→(KPGD) Punta Gorda, Florida, United States
    Cessna Citation CJ4
    $14,933
  • Sun, Jul 12
    (KPWK) Chicago, Illinois, United States→(KPVU) Provo, Utah, United States
    Bombardier Challenger 300
    $33,902
  • Sun, Jul 12
    (KMDW) Chicago, Illinois, United States→(KFCM) Minneapolis, Minnesota, United States
    Bombardier Challenger 300
    $13,400
  • Mon, Jul 13
    (KMKE) Milwaukee, Wisconsin, United States→(KPSM) Portsmouth, New Hampshire, United States
    Cessna Citation CJ4
    $11,615

    • Frequently asked about Chicago empty legs

    How many empty leg flights are available from Chicago?
    97 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.