Empty leg flights from Chicago

LIVE44 departing · 48 arriving

44 empty legs are departing Chicago right now and 48 flights are arriving, listed by the operators flying them and refreshed through the day. Today's legs use Chicago Executive Airport (PWK), Dupage Airport (DPA), Chicago Midway International Airport (MDW) and Gary Chicago International Airport (GYY). Prices marked Estimated are ours; the rest are the operator's own.

Departing Chicago

Soonest first. Every row opens the full listing.

Today, Sep 7
Chicago
Washington D.C.
Challenger 300/350
Super Mid
8 seats
Good valueSuper MidChallenger 300/350
Estimated total
$6k–$8.8k
Today, Sep 7
Chicago
Memphis
Challenger 300/350
Super Mid
8 seats
Good valueSuper MidChallenger 300/350
Estimated total
$5.2k–$8k
Tomorrow, Sep 8
ChicagoKPWK
New YorkKFRG
Gulfstream G550
Ultra Long Range
16 seats
Ultra Long RangeGulfstream G550
Estimated total
$17k–$26k
Tomorrow, Sep 8
ChicagoKDPA
HaydenKHDN
Bombardier Challenger 604
Heavy
9 seats
HeavyBombardier Challenger 604
Estimated total
$15k–$23k
Tomorrow, Sep 8
ChicagoKORD
BrainerdKBRD
Bombardier Learjet 60
Mid
7 seats
Market rateMidBombardier Learjet 60
Estimated total
$7k–$11k
Wed, Sep 9
Chicago
Hayden
Challenger 300/350
Super Mid
8 seats
Good valueSuper MidChallenger 300/350
Estimated total
$10k–$16k
Wed, Sep 9
Chicago
Nashville
Challenger 300/350
Super Mid
8 seats
Great dealSuper MidChallenger 300/350
Estimated total
$4k–$6.3k
Wed, Sep 9
Chicago
San Antonio
Global 5000/6000
Ultra Long Range
8 seats
Good valueUltra Long RangeGlobal 5000/6000
Estimated total
$14k–$21k
Thu, Sep 10
ChicagoKUGN
ScottsdaleKSDL
Gulfstream GIV-SP
Heavy
12 seats
HeavyGulfstream GIV-SP
Estimated total
$27k–$41k
Thu, Sep 10
ChicagoKDPA
TulsaKTUL
Bombardier Challenger 605
Heavy
10 seats
Market rateHeavyBombardier Challenger 605
Estimated total
$11k–$16k
Thu, Sep 10
ChicagoKMDW
HartfordKHVN
Cessna Citation XLS
Mid
9 seats
Market rateMidCessna Citation XLS
Estimated total
$8.5k–$13k
Sat, Sep 12
Chicago
Indianapolis
Global 5000/6000
Ultra Long Range
8 seats
Good valueUltra Long RangeGlobal 5000/6000
Estimated total
$6.2k–$9.3k
Sep 13 → Sep 18Flexible · time set with operator
ChicagoKGYY
ClevelandKCLE
Nextant 400XTi
Light
7 seats
LightNextant 400XTi
Estimated total
$3.5k–$5.3k
Sun, Sep 13
ChicagoKGYY
Palm BeachKSUA
Bombardier Global 5000
Ultra Long Range
13 seats
Ultra Long RangeBombardier Global 5000
Estimated total
$23k–$35k
Sep 14 → Sep 19Flexible · time set with operator
ChicagoKGYY
PellaKPEA
Cirrus Vision Jet SF50
Light
5 seats
LightCirrus Vision Jet SF50
Estimated total
$2.2k–$3.8k
Sep 16 → Sep 21Flexible · time set with operator
ChicagoKDPA
NaplesKAPF
Hawker 850XP
Mid
8 seats
MidHawker 850XP
Estimated total
$12k–$18k
Thu, Sep 17
ChicagoKORD
OmahaKOMA
Cessna Citation XLS
Mid
9 seats
Good valueMidCessna Citation XLS
Estimated total
$4.5k–$6.5k
Sep 21 → Sep 23Flexible · time set with operator
ChicagoKDPA
New YorkKMMU
Gulfstream G500
Ultra Long Range
15 seats
Ultra Long RangeGulfstream G500
Estimated total
$17k–$25k
Mon, Sep 21
ChicagoKPWK
DenverKAPA
Bombardier Global 6000
Ultra Long Range
16 seats
Ultra Long RangeBombardier Global 6000
Estimated total
$22k–$33k
Sep 22 → Sep 23Flexible · time set with operator
ChicagoKMDW
New YorkKISP
Cessna Citation Sovereign
Super Mid
9 seats
Super MidCessna Citation Sovereign
Estimated total
$10k–$15k
All 44 flights from Chicago

Arriving in Chicago

Legs ending in Chicago, soonest first.

All 48 flights to Chicago

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Empty leg routes from Chicago

Empty leg routes to Chicago

How empty legs from Chicago work

An empty leg is a repositioning flight. A jet that dropped its passengers in Chicago has to fly back to base, or fly out to its next job, and the operator would rather sell the seats than fly the cabin empty. That is why the price is a fraction of a normal charter for the same aircraft, same crew, same operator.

The route and the date are set by the aircraft's schedule, not yours. A listing that shows a date with no time means the operator has not fixed the departure yet; you settle it with them when you request. Legs appear anywhere from weeks to a day ahead and can be withdrawn when the operator's plans change.

UpLeg lists these legs free of charge. You request one, we confirm your exact total with the operator before you sign, and you pay the operator directly. There is no membership and no card on file.

More in the FAQ, or read how UpLeg works.

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