Empty leg flights available Chicago O'hare International Airport (KORD)

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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Teterboro (KTEB) to Chicago (KORD)

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April 11, 2026 - April 12, 2026

8 passengers

1.4 hours in flight

Cessna Citation XLS (Midsize jet)

Aircraft photos: 2

Cessna Citation XLS empty leg from Teterboro (KTEB) to Chicago (KORD) photo 1

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What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 23,830

Price without Membership:

USD 26,210

Availability confirmation required.

New Haven (KHVN) to Chicago (KORD)

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April 11, 2026 - April 12, 2026

8 passengers

1.6 hours in flight

Cessna Citation XLS (Midsize jet)

Aircraft photos: 2

Cessna Citation XLS empty leg from New Haven (KHVN) to Chicago (KORD) photo 1

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What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 16,210

Price without Membership:

USD 17,830

Availability confirmation required.

Chicago (KORD) to Cleveland (KCGF)

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April 11, 2026 - April 11, 2026

7 passengers

1.0 hours in flight

Bombardier Learjet 40XR (Super light jet)

Aircraft photos: 2

Bombardier Learjet 40XR empty leg from Chicago (KORD) to Cleveland (KCGF) photo 1

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What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 6,500

Price without Membership:

USD 7,150

Availability confirmation required.

Cleveland (KCLE) to Chicago (KORD)

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April 23, 2026 - April 23, 2026

7 passengers

1.0 hours in flight

Bombardier Learjet 40XR (Super light jet)

Aircraft photos: 2

Bombardier Learjet 40XR empty leg from Cleveland (KCLE) to Chicago (KORD) photo 1

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What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 10,400

Price without Membership:

USD 11,440

Availability confirmation required.

Chicago (KORD) to Kansas City (KMKC)

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September 4, 2026 - September 4, 2026

10 passengers

1.0 hours in flight

Bombardier Challenger 3500 (Super midsize jet)

Aircraft photos: 2

Bombardier Challenger 3500 empty leg from Chicago (KORD) to Kansas City (KMKC) photo 1

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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.

Kansas City (KMKC) to Chicago (KORD)

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September 13, 2026 - September 13, 2026

10 passengers

1.0 hours in flight

Bombardier Challenger 3500 (Super midsize jet)

Aircraft photos: 2

Bombardier Challenger 3500 empty leg from Kansas City (KMKC) to Chicago (KORD) 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.

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.