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Private jets in Chicago, IL
Home/Empty Leg Flights/Chicago
IL · United States

Chicago empty leg flights

Chicago empty leg flights are one-way private jet repositioning flights in and out of Chicago metro, typically 25 to 75% below a comparable full charter. Right now 49 legs depart the Chicago area and 8 arrive at Chicago Executive (KPWK).

See 49 departuresSee 8 arrivalsfrom $3,538 one-way, whole aircraft

Empty legs departing Chicago (49)

One-way legs from Chicago Executive (KPWK) and every charter field within 80 miles. Updated hourly.

  • Thu, Oct 15$4,355
    Chicago, IL (KMDW)
    ↓
    Pontiac, MI (KPTK)
    Cessna Citation II
  • Thu, Oct 15$6,834
    Chicago, IL (KMDW)
    ↓
    Akron, OH (KCAK)
    Dassault Falcon 2000
  • Thu, Oct 15$8,710
    Waukesha, WI (KUES)
    ↓
    Nashville, TN (KJWN)
    Cessna Citation Excel
  • Thu, Oct 15$7,961
    Chicago, IL (KMDW)
    ↓
    Saint Paul, MN (KSTP)
    Bombardier Learjet 60
  • Thu, Oct 15$3,538
    Chicago, IL (KORD)
    ↓
    Zanesville, OH (KZZV)
    Cessna Citation CJ2
  • Fri, Oct 16$6,164
    Gary, IN (KGYY)
    ↓
    Chicago, IL (KDPA)
    Cessna Citation XLS
  • Fri, Oct 16$10,376
    Chicago, IL (KDPA)
    ↓
    Jacksonville, FL (KJAX)
    Cessna Citation XLS+
  • Sat, Oct 17$8,710
    Chicago, IL (KARR)
    ↓
    Sevierville, TN (KGKT)
    Dassault Falcon 900
  • Sat, Oct 17$4,037
    Chicago/Prospect Heights/Wheeling, IL (KPWK)
    ↓
    Lansing, MI (KLAN)
    Cessna Citation XLS+
  • Sun, Oct 18$7,728
    Chicago/Prospect Heights/Wheeling, IL (KPWK)
    ↓
    Cleveland, OH (KCLE)
    Beech Beechjet 400A
  • Mon, Oct 19$13,400
    Milwaukee, WI (KMKE)
    ↓
    Pontiac, MI (KPTK)
    Bombardier Challenger 300
  • Mon, Oct 19$6,164
    Chicago, IL (KDPA)
    ↓
    Gary, IN (KGYY)
    Cessna Citation XLS
  • Tue, Oct 20$8,236
    Chicago/Waukegan, IL (KUGN)
    ↓
    Pontiac, MI (KPTK)
    Bombardier Challenger 604
  • Tue, Oct 20$4,363
    Milwaukee, WI (KMKE)
    ↓
    Kalamazoo, MI (KAZO)
    Cessna Citation III
  • Tue, Oct 20$6,700
    Chicago, IL (KMDW)
    ↓
    Louisville, KY (KSDF)
    Cessna Citation CE560XL (XLS+)
  • Wed, Oct 21$5,503
    Chicago/West Chicago, IL (KDPA)
    ↓
    Gallatin, TN (KXNX)
    Cirrus SF 50 Vision Jet
  • Thu, Oct 22$18,695
    Milwaukee, WI (KMKE)
    ↓
    Marana, AZ (KAVQ)
    Cessna Citation CJ4
  • Thu, Oct 22$6,998
    Janesville, WI (KJVL)
    ↓
    Nashville, TN (KBNA)
    Beechcraft Hawker 850XP
  • Fri, Oct 23$13,590
    Waukesha, WI (KUES)
    ↓
    Eagle, CO (KEGE)
    Cessna Citation CJ4
  • Fri, Oct 23$27,917
    Gary, IN (KGYY)
    ↓
    Tulsa, OK (KTUL)
    Gulfstream GV
  • Fri, Oct 23$15,608
    Chicago, IL (KDPA)
    ↓
    Houston, TX (KHOU)
    Cessna Citation Excel
  • Tue, Oct 27$5,939
    Chicago/Waukegan, IL (KUGN)
    ↓
    Rochester, MN (KRST)
    Gulfstream G200
  • Wed, Oct 28$6,164
    Gary, IN (KGYY)
    ↓
    Fond du Lac, WI (KFLD)
    Cessna Citation XLS
  • Wed, Oct 28$8,189
    Chicago, IL (KPWK)
    ↓
    Chicago, IL (KARR)
    Dassault Falcon 900

View all 49 departures

Empty legs arriving in Chicago (8)

One-way legs into Chicago Executive (KPWK). Updated hourly.

  • Thu, Oct 15$12,730
    Dallas, TX (KADS)
    ↓
    Chicago, IL (PWK)
    Dassault Falcon 900
  • Thu, Oct 15$7,333
    Cleveland, OH (KCLE)
    ↓
    Chicago, IL (PWK)
    Beech Beechjet 400A
  • Sun, Oct 18$6,586
    Minneapolis, MN (KMSP)
    ↓
    Chicago, IL (PWK)
    Embraer Praetor 500
  • Wed, Oct 28$11,467
    Punta Gorda, FL (KPGD)
    ↓
    Chicago, IL (PWK)
    Cessna Citation V
  • Sun, Nov 8$4,958
    Alcoa, TN (KTYS)
    ↓
    Chicago, IL (PWK)
    Beechcraft King Air 250

View all 8 arrivals

Prices are for the whole aircraft, with taxes and fees shown at checkout.

Flying private in and out of Chicago

Chicago (Chicago metro) sees steady private-jet traffic, and as the business hub of the Midwest, Chicago feeds steady corporate repositioning in every direction. Empty legs, the one-way repositioning flights operators fly between charters, are what you book here, priced 25 to 75% below a comparable full charter.

SkyAccess anchors Chicago searches on Chicago Executive (KPWK) and scans a 80-mile radius, so a single search surfaces empty legs across Chicago Executive, Chicago Midway, DuPage and the wider IL cluster: not just one airport.

Why fly private to Chicago

Built for the schedule

Chicago's corporate flyers fly private to compress a multi-day commercial itinerary into a same-day round trip: and empty legs make that economics work on the right dates.

Empty-leg economics

Because an empty leg is a flight the operator is already making between charters, Chicago repositioning legs typically sell 25 to 75% below a comparable full charter, and operators can set a listing's price to step down as departure approaches.

Skip the terminal

Flying private into Chicago means an FBO arrival: no terminal, no TSA line, and a few minutes from touchdown to your car.

What an empty leg in Chicago costs

Empty-leg pricing to Chicago runs 25 to 75% below a comparable full charter, with the steepest discounts in the 24 to 72 hours before departure, when the operator most needs to fill the repositioning flight. Because the aircraft is flying that leg regardless, the saving comes without compromising the aircraft or crew.

Popular private jet routes to and from Chicago

New York, NY → Chicago, ILView route →Minneapolis, MN → Chicago, ILView route →Detroit, MI → Chicago, ILView route →Milwaukee, WI → Chicago, ILView route →Kansas City, MO → Chicago, ILView route →Indianapolis, IN → Chicago, ILView route →

Empty legs at the airports serving Chicago

Chicago Executive (KPWK) empty legs
The metro's primary business-jet airport, in Wheeling north of the city.
Chicago Midway (KMDW) empty legs
Close-in field handling larger charter aircraft.
DuPage (KDPA) empty legs
Western-suburbs corporate field.

Aircraft that fly in and out of Chicago

Midsize and super-midsize jets dominate Chicago corporate flying; light jets cover regional Midwest hops. Chicago Executive is the GA hub of choice; Midway handles larger charter.

Chicago empty leg FAQs

How many empty leg flights are available in Chicago right now?+
Right now 49 empty leg flights depart the Chicago area and 8 arrive at Chicago Executive (KPWK) on SkyAccess. They come from certified charter operators repositioning aircraft, and the counts change through the day as new legs publish and others book.
How much does an empty leg flight in Chicago cost?+
Empty-leg pricing to Chicago runs 25 to 75% below a comparable full charter, with the steepest discounts in the 24 to 72 hours before departure, when the operator most needs to fill the repositioning flight. Because the aircraft is flying that leg regardless, the saving comes without compromising the aircraft or crew. Prices are for the whole aircraft, with taxes and fees shown at checkout.
Which airports serve Chicago private jet flights?+
Chicago Executive (KPWK), Chicago Midway (KMDW), DuPage (KDPA). SkyAccess searches a 80-mile radius around Chicago Executive (KPWK), so one Chicago search surfaces empty legs across every charter-friendly field in the cluster.
What aircraft fly empty legs in and out of Chicago?+
Midsize and super-midsize jets dominate Chicago corporate flying; light jets cover regional Midwest hops. Chicago Executive is the GA hub of choice; Midway handles larger charter.
When is the best time to book an empty leg in Chicago?+
Chicago is a year-round business market, busiest spring through fall; deep winter weather can disrupt schedules and occasionally deepens last-minute empty-leg discounts. Midweek inventory is heaviest. For the deepest discount within the season, search inside the 24 to 72 hour window before departure, when operators most need to fill a repositioning leg.

At a glance

Live departures
49
Live arrivals
8
From
$3,538
Primary airport
KPWK
Region
IL
Country
United States
Search departuresSearch arrivals

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