Empty leg flights available Dupage Airport (KDPA)

Chicago/west 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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Orlando (KSFB) to Chicago/West Chicago (KDPA)

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March 26, 2026 - March 26, 2026

9 passengers

2.1 hours in flight

Cessna Citation Longitude (Super midsize jet)

Aircraft photos: 2

Cessna Citation Longitude empty leg from Orlando (KSFB) to Chicago/West Chicago (KDPA) photo 1

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What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 21,680

Price without Membership:

USD 23,850

Availability confirmation required.

Teterboro (KTEB) to Chicago/West Chicago (KDPA)

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March 27, 2026 - March 27, 2026

10 passengers

1.4 hours in flight

Bombardier Challenger 300 (Super midsize jet)

Aircraft photos: 2

Bombardier Challenger 300 empty leg from Teterboro (KTEB) to Chicago/West Chicago (KDPA) photo 1

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What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 22,600

Price without Membership:

USD 24,860

Availability confirmation required.

Teterboro (KTEB) to Chicago/West Chicago (KDPA)

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March 28, 2026 - March 28, 2026

13 passengers

1.3 hours in flight

Gulfstream G600(GVII) (Ultra long range)

Aircraft photos: 2

Gulfstream G600(GVII) empty leg from Teterboro (KTEB) to Chicago/West Chicago (KDPA) photo 1

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What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 10,770

Price without Membership:

USD 11,850

Availability confirmation required.

Chicago/West Chicago (KDPA) to St Louis (KSUS)

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April 3, 2026 - April 4, 2026

8 passengers

1.0 hours in flight

Beechcraft Hawker 800XPi (Midsize jet)

Aircraft photos: 2

Beechcraft Hawker 800XPi empty leg from Chicago/West Chicago (KDPA) to St Louis (KSUS) 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.

Chicago/West Chicago (KDPA) to Marathon (KMTH)

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April 4, 2026 - April 5, 2026

8 passengers

2.4 hours in flight

Beechcraft Hawker 800XPi (Midsize jet)

Aircraft photos: 2

Beechcraft Hawker 800XPi empty leg from Chicago/West Chicago (KDPA) to Marathon (KMTH) photo 1

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What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 25,520

Price without Membership:

USD 28,070

Availability confirmation required.

Chicago/West Chicago (KDPA) to Teterboro (KTEB)

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April 6, 2026 - April 6, 2026

9 passengers

1.6 hours in flight

Cessna Citation Longitude (Super midsize jet)

Aircraft photos: 2

Cessna Citation Longitude empty leg from Chicago/West Chicago (KDPA) to Teterboro (KTEB) photo 1

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What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 16,190

Price without Membership:

USD 17,810

Availability confirmation required.

Chicago/West Chicago (KDPA) to Teterboro (KTEB)

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April 6, 2026 - April 6, 2026

10 passengers

1.4 hours in flight

Bombardier Challenger 300 (Super midsize jet)

Aircraft photos: 2

Bombardier Challenger 300 empty leg from Chicago/West Chicago (KDPA) to Teterboro (KTEB) photo 1

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What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 22,600

Price without Membership:

USD 24,860

Availability confirmation required.

Manassas (KHEF) to Chicago/West Chicago (KDPA)

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April 8, 2026 - April 8, 2026

13 passengers

1.0 hours in flight

Embraer Legacy 650 (Heavy jet)

Aircraft photos: 2

Embraer Legacy 650 empty leg from Manassas (KHEF) to Chicago/West Chicago (KDPA) photo 1

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What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 14,400

Price without Membership:

USD 15,840

Availability confirmation required.

Chicago/West Chicago (KDPA) to Houston (KCXO)

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April 9, 2026 - April 9, 2026

13 passengers

1.5 hours in flight

Embraer Legacy 650 (Heavy jet)

Aircraft photos: 2

Embraer Legacy 650 empty leg from Chicago/West Chicago (KDPA) to Houston (KCXO) photo 1

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What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 19,000

Price without Membership:

USD 20,900

Availability confirmation required.

Chicago/West Chicago (KDPA) to Detroit (KDET)

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March 11, 2026 - March 14, 2026

12 passengers

1.0 hours in flight

Gulfstream GIV-SP (Heavy jet)

Aircraft photos: 2

Gulfstream GIV-SP empty leg from Chicago/West Chicago (KDPA) to Detroit (KDET) photo 1

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What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 28,690

Price without Membership:

USD 31,560

Availability confirmation required.

Lafayette (KLAF) to Chicago/West Chicago (KDPA)

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March 7, 2026 - March 7, 2026

7 passengers

1.0 hours in flight

Bombardier Learjet 60 (Midsize jet)

Aircraft photos: 2

Bombardier Learjet 60 empty leg from Lafayette (KLAF) to Chicago/West Chicago (KDPA) photo 1

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What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 3,600

Price without Membership:

USD 3,960

Availability confirmation required.

Columbus (KCMH) to Chicago/West Chicago (KDPA)

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March 7, 2026 - March 7, 2026

7 passengers

1.0 hours in flight

Bombardier Learjet 60 (Midsize jet)

Aircraft photos: 2

Bombardier Learjet 60 empty leg from Columbus (KCMH) to Chicago/West Chicago (KDPA) photo 1

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What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 6,700

Price without Membership:

USD 7,370

Availability confirmation required.

Toronto (CYYZ) to Chicago/West Chicago (KDPA)

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March 2, 2026 - March 6, 2026

12 passengers

1.0 hours in flight

Gulfstream GIV-SP (Heavy jet)

Aircraft photos: 2

Gulfstream GIV-SP empty leg from Toronto (CYYZ) to Chicago/West Chicago (KDPA) photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 28,690

Price without Membership:

USD 31,560

Availability confirmation required.

Chicago/West Chicago (KDPA) to West Palm Beach (KPBI)

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February 28, 2026 - March 4, 2026

9 passengers

2.1 hours in flight

Gulfstream G200 (Super midsize jet)

Aircraft photos: 2

Gulfstream G200 empty leg from Chicago/West Chicago (KDPA) to West Palm Beach (KPBI) photo 1

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What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 17,500

Price without Membership:

USD 19,250

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.