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  5. From Chicago

Empty Leg Flights From Chicago — 37 Live

37 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 37)

  • Sat, May 23
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KIMT) Kingsford, Michigan, United States
    Cessna Citation CJ1
    $2,946
  • Sun, May 24
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KSDL) Scottsdale, Arizona, United States
Beechcraft Hawker 850XP
$19,910
  • Mon, May 25
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KTEB) Teterboro, New Jersey, United States
    Challenger 601
    $20,033
  • Mon, May 25
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KEDC) Pflugerville, Texas, United States
    Cessna Citation X
    $11,604
  • Mon, May 25
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KEGV) Eagle River, Wisconsin, United States
    Cessna Citation XLS+
    $5,120
  • Mon, May 25
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KTEB) Teterboro, New Jersey, United States
    Bombardier Challenger 601-3A
    $9,146
  • Tue, May 26
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KBCT) Boca Raton, Florida, United States
    Cessna Citation V
    $20,100
  • Tue, May 26
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KGRR) Grand Rapids, Michigan, United States
    Cessna Citation XLS+
    $3,545
  • Tue, May 26
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KCHA) Chattanooga, Tennessee, United States
    Beechcraft Baron 58
    $4,422
  • Wed, May 27
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KBCT) Boca Raton, Florida, United States
    Cessna Citation V
    $24,120
  • Wed, May 27
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport→(KRHI) Rhinelander, Wisconsin, United States - Rhinelander Oneida County Airport
    Embraer Praetor 500
    $5,661
  • Sat, May 30
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KLEE) Leesburg, Florida, United States
    Cessna Citation XLS+
    $24,120
  • Sat, May 30
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KCHO) Charlottesville, Virginia, United States
    Cessna Citation CJ3+
    $12,804
  • Sun, May 31
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport→(KDTS) Destin, Florida, United States - Destin Executive Airport
    Bombardier Learjet 45
    $12,508
  • Sun, May 31
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport→(KLEE) Leesburg, Florida, United States - Leesburg International Airport
    Cessna Citation XLS+
    $19,524
  • Sun, May 31
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KDTS) Destin, Florida, United States
    Bombardier Learjet 45
    $9,153
  • Sun, May 31
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KLEE) Leesburg, Florida, United States
    Cessna Citation XLS+
    $10,301
  • Wed, Jun 3
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport→(KFTW) Fort Worth, Texas, United States - Fort Worth Meacham International Airport
    Bombardier Learjet 60
    $8,524
  • Wed, Jun 3
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport→(KFTW) Fort Worth, Texas, United States - Fort Worth Meacham International Airport
    Bombardier Learjet 60
    $15,946
  • Sun, Jun 7
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KPWA) Oklahoma City, Oklahoma, United States
    Cessna Citation Ultra
    $7,665
  • Mon, Jun 8
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport→(KAPF) Naples, Florida, United States - Naples Municipal Airport
    Cessna Citation XLS
    $15,661
  • Wed, Jun 10
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KMSP) Minneapolis, Minnesota, United States
    Pilatus PC 24
    $4,611
  • Thu, Jun 11
    (KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States→(KGYY) Gary, Indiana, United States
    Beechcraft Hawker 900XP
    $2,389
  • 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

    • Frequently asked about Chicago empty legs

    How many empty leg flights are available from Chicago?
    37 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.