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  5. To Chicago

Empty Leg Flights To Chicago — 19 Live

19 live empty leg flights arriving in 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 departures from ChicagoSearch all empty legs

Arriving in Chicago (19)

  • Mon, May 25
    (KSBN) South Bend, Indiana, United States→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States
    Embraer Praetor 500
    $3,466
  • Tue, May 26
    (KSUS) St Louis, Missouri, United States→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States
Bombardier Learjet 60
$3,854
  • Tue, May 26
    (KSUS) St Louis, Missouri, United States→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States
    Bombardier Learjet 60
    $3,854
  • Tue, May 26
    (KSUS) St Louis, Missouri, United States - Spirit of St Louis Airport→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport
    Bombardier Learjet 60
    $4,971
  • Sun, May 31
    (KSTL) St Louis, Missouri, United States→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States
    Bombardier Challenger 300
    $10,519
  • Mon, Jun 1
    (KCCR) Concord, California, United States→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States
    Cessna Citation V
    $24,388
  • Thu, Jun 4
    (KRSW) Fort Myers, Florida, United States - Southwest Florida International Airport→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport
    Cessna Citation XLS
    $15,282
  • Sun, Jun 7
    (KGYY) Gary, Indiana, United States→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States
    Beechcraft Hawker 900XP
    $2,389
  • Thu, Jun 11
    (KIMT) Iron Mountain / Kingsford, Michigan, United States - Ford Airport→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport
    Cessna Citation XLS+
    $4,923
  • Sun, Jun 14
    (KHPN) White Plains, New York, United States→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States
    Cessna Citation Sovereign
    $9,193
  • Mon, Jun 15
    (KFOK) Westhampton Beach, New York, United States→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States
    Hawker 4000
    $14,751
  • Fri, Jun 19
    (CYHM) Hamilton, Canada→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States
    Gulfstream G100
    $6,748
  • Fri, Jun 19
    (KEGV) Eagle River, Wisconsin, United States→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States
    Cessna Citation XLS+
    $5,120
  • Fri, Jun 19
    (KMCO) Orlando, Florida, United States - Orlando International Airport→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States - Chicago Executive Airport
    Bombardier Learjet 45
    $15,799
  • Sat, Jun 20
    (KMCO) Orlando, Florida, United States→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States
    Bombardier Learjet 45
    $11,031
  • Sat, Jun 20
    (KOMA) Omaha, Nebraska, United States→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States
    Cessna Citation Excel
    $6,700
  • Wed, Jul 8
    (KGRR) Grand Rapids, Michigan, United States→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States
    Cessna Citation XLS
    $3,015
  • Mon, Jul 13
    (KFMY) Fort Myers, Florida, United States→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States
    Embraer Praetor 500
    $16,984
  • Thu, Sep 3
    (KASW) Warsaw, Indiana, United States→(KPWK) Chicago/Prospect Heights/Wheeling, Illinois, United States
    Bombardier Challenger 605
    $4,774

    • Frequently asked about Chicago empty legs

    How many empty leg flights are available to Chicago?
    19 live empty leg flights arriving in Chicago right now 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 to Chicago?
    Typical empty leg pricing to 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 to 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.