EMPTYLEG STORE
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Empty leg flights available Chicago Midway International Airport (KMDW)

Chicago, Illinois, Us. Empty legs are discounted repositioning flights. Routes and timing can change quickly — request a leg and we confirm availability.

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Chicago (KMDW) to Mattoon/Charleston (KMTO)

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May 26, 2026 - May 26, 2026
7 passengers
1.0 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from Chicago (KMDW) to Mattoon/Charleston (KMTO) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 23,490
Price without Membership:
USD 25,840
Availability confirmation required.

Farmingdale (KFRG) to Chicago (KMDW)

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May 28, 2026 - May 28, 2026
16 passengers
1.3 hours in flight
Gulfstream G550 (Ultra long range)
Aircraft photos: 2
Gulfstream G550 empty leg from Farmingdale (KFRG) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 11,000
Price without Membership:
USD 12,100
Availability confirmation required.

Chicago (KMDW) to Farmingdale (KFRG)

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May 31, 2026 - May 31, 2026
16 passengers
1.3 hours in flight
Gulfstream G550 (Ultra long range)
Aircraft photos: 2
Gulfstream G550 empty leg from Chicago (KMDW) to Farmingdale (KFRG) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 11,000
Price without Membership:
USD 12,100
Availability confirmation required.

Duluth (KDLH) to Chicago (KMDW)

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June 7, 2026 - June 7, 2026
7 passengers
1.0 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 1
Bombardier Learjet 60 empty leg from Duluth (KDLH) to Chicago (KMDW) photo 1
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 6,000
Price without Membership:
USD 6,600
Availability confirmation required.

Teterboro (KTEB) to Chicago (KMDW)

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June 8, 2026 - June 8, 2026
14 passengers
1.2 hours in flight
Gulfstream G IV SP (Heavy jet)
Aircraft photos: 2
Gulfstream G IV SP empty leg from Teterboro (KTEB) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 10,580
Price without Membership:
USD 11,630
Availability confirmation required.

Pellston (KPLN) to Chicago (KMDW)

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June 10, 2026 - June 10, 2026
7 passengers
1.0 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from Pellston (KPLN) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 23,490
Price without Membership:
USD 25,840
Availability confirmation required.

Chicago (KMDW) to Memphis (KMEM)

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June 14, 2026 - June 14, 2026
7 passengers
1.0 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 1
Bombardier Learjet 60 empty leg from Chicago (KMDW) to Memphis (KMEM) photo 1
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 9,100
Price without Membership:
USD 10,010
Availability confirmation required.

Akron (KCAK) to Chicago (KMDW)

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June 23, 2026 - June 23, 2026
7 passengers
1.0 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from Akron (KCAK) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 7,200
Price without Membership:
USD 7,920
Availability confirmation required.

How empty legs work

Empty legs appear when an aircraft needs to reposition for its next charter. These segments are often listed at a reduced price.

These deals are availability-based and often last-minute. Once you request a flight, our team confirms details directly with dispatch.