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Empty leg flights available Gary Chicago International Airport (KGYY)

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

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Naples (KAPF) to Gary (KGYY)

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March 24, 2026 - March 24, 2026
9 passengers
2.2 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from Naples (KAPF) to Gary (KGYY) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 23,290
Price without Membership:
USD 25,620
Availability confirmation required.

Gary (KGYY) to Nashville (KBNA)

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March 25, 2026 - March 25, 2026
9 passengers
1.0 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from Gary (KGYY) to Nashville (KBNA) 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.

Gary (KGYY) to Naples (KAPF)

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March 25, 2026 - March 26, 2026
9 passengers
2.2 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from Gary (KGYY) to Naples (KAPF) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 23,290
Price without Membership:
USD 25,620
Availability confirmation required.

Gary (KGYY) to Sarasota/Bradenton (KSRQ)

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April 6, 2026 - April 6, 2026
9 passengers
2.0 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from Gary (KGYY) to Sarasota/Bradenton (KSRQ) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 21,300
Price without Membership:
USD 23,430
Availability confirmation required.

Gary (KGYY) to Naples (KAPF)

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April 8, 2026 - April 8, 2026
9 passengers
2.2 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from Gary (KGYY) to Naples (KAPF) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 23,290
Price without Membership:
USD 25,620
Availability confirmation required.

Gary (KGYY) to Road Town (TUPJ)

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April 14, 2026 - April 14, 2026
10 passengers
3.9 hours in flight
Bombardier Challenger 300 (Super midsize jet)
Aircraft photos: 2
Bombardier Challenger 300 empty leg from Gary (KGYY) to Road Town (TUPJ) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 19,210
Price without Membership:
USD 21,130
Availability confirmation required.

Sarasota/Bradenton (KSRQ) to Gary (KGYY)

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April 19, 2026 - April 20, 2026
10 passengers
1.9 hours in flight
Bombardier Challenger 300 (Super midsize jet)
Aircraft photos: 2
Bombardier Challenger 300 empty leg from Sarasota/Bradenton (KSRQ) to Gary (KGYY) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 19,730
Price without Membership:
USD 21,700
Availability confirmation required.

Gary (KGYY) to Big Ambergris Cay (MBAC)

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April 22, 2026 - April 22, 2026
10 passengers
3.1 hours in flight
Bombardier Challenger 300 (Super midsize jet)
Aircraft photos: 2
Bombardier Challenger 300 empty leg from Gary (KGYY) to Big Ambergris Cay (MBAC) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 15,400
Price without Membership:
USD 16,940
Availability confirmation required.

Des Moines (KDSM) to Gary (KGYY)

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March 23, 2026 - March 23, 2026
9 passengers
1.0 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from Des Moines (KDSM) to Gary (KGYY) 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.

Naples (KAPF) to Gary (KGYY)

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March 22, 2026 - March 22, 2026
9 passengers
2.2 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from Naples (KAPF) to Gary (KGYY) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 23,290
Price without Membership:
USD 25,620
Availability confirmation required.

Des Moines (KDSM) to Gary (KGYY)

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March 21, 2026 - March 21, 2026
6 passengers
1.0 hours in flight
Honda Aircraft HA-420 HondaJet (Entry level jet (VLJ))
Aircraft photos: 2
Honda Aircraft HA-420 HondaJet empty leg from Des Moines (KDSM) to Gary (KGYY) photo 1
1 / 2
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.

Gary (KGYY) to Naples (KAPF)

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March 17, 2026 - March 17, 2026
9 passengers
2.2 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from Gary (KGYY) to Naples (KAPF) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 23,290
Price without Membership:
USD 25,620
Availability confirmation required.

Des Moines (KDSM) to Gary (KGYY)

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March 17, 2026 - March 17, 2026
6 passengers
1.0 hours in flight
Honda Aircraft HA-420 HondaJet (Entry level jet (VLJ))
Aircraft photos: 2
Honda Aircraft HA-420 HondaJet empty leg from Des Moines (KDSM) to Gary (KGYY) photo 1
1 / 2
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.

Gary (KGYY) to Naples (KAPF)

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March 16, 2026 - March 17, 2026
9 passengers
2.2 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from Gary (KGYY) to Naples (KAPF) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 23,290
Price without Membership:
USD 25,620
Availability confirmation required.

Gary (KGYY) to Naples (KAPF)

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March 15, 2026 - March 15, 2026
9 passengers
2.2 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from Gary (KGYY) to Naples (KAPF) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 23,290
Price without Membership:
USD 25,620
Availability confirmation required.

Stuart (KSUA) to Gary (KGYY)

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March 13, 2026 - March 13, 2026
6 passengers
2.6 hours in flight
Honda Aircraft HA-420 HondaJet (Entry level jet (VLJ))
Aircraft photos: 2
Honda Aircraft HA-420 HondaJet empty leg from Stuart (KSUA) to Gary (KGYY) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 19,910
Price without Membership:
USD 21,900
Availability confirmation required.

Gary (KGYY) to Atlanta (KPDK)

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March 13, 2026 - March 13, 2026
9 passengers
1.1 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from Gary (KGYY) to Atlanta (KPDK) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 5,560
Price without Membership:
USD 6,120
Availability confirmation required.

Gary (KGYY) to Morgantown (KMGW)

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March 10, 2026 - March 10, 2026
6 passengers
1.0 hours in flight
Honda Aircraft HA-420 HondaJet (Entry level jet (VLJ))
Aircraft photos: 2
Honda Aircraft HA-420 HondaJet empty leg from Gary (KGYY) to Morgantown (KMGW) photo 1
1 / 2
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.

Atlanta (KFTY) to Gary (KGYY)

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March 9, 2026 - March 9, 2026
9 passengers
1.1 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from Atlanta (KFTY) to Gary (KGYY) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 26,500
Price without Membership:
USD 29,150
Availability confirmation required.

Atlanta (KPDK) to Gary (KGYY)

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March 9, 2026 - March 9, 2026
9 passengers
1.1 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from Atlanta (KPDK) to Gary (KGYY) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 26,360
Price without Membership:
USD 29,000
Availability confirmation required.

Fernandina Beach (KFHB) to Gary (KGYY)

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March 6, 2026 - March 7, 2026
6 passengers
2.0 hours in flight
Honda Aircraft HA-420 HondaJet (Entry level jet (VLJ))
Aircraft photos: 2
Honda Aircraft HA-420 HondaJet empty leg from Fernandina Beach (KFHB) to Gary (KGYY) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 15,330
Price without Membership:
USD 16,860
Availability confirmation required.

Fernandina Beach (KFHB) to Gary (KGYY)

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March 6, 2026 - March 6, 2026
6 passengers
2.0 hours in flight
Honda Aircraft HA-420 HondaJet (Entry level jet (VLJ))
Aircraft photos: 2
Honda Aircraft HA-420 HondaJet empty leg from Fernandina Beach (KFHB) to Gary (KGYY) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 15,330
Price without Membership:
USD 16,860
Availability confirmation required.

Pontiac (KPTK) to Gary (KGYY)

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March 2, 2026 - March 2, 2026
9 passengers
1.0 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from Pontiac (KPTK) to Gary (KGYY) 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.

Sarasota/Bradenton (KSRQ) to Gary (KGYY)

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March 2, 2026 - March 2, 2026
9 passengers
2.0 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from Sarasota/Bradenton (KSRQ) to Gary (KGYY) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 21,300
Price without Membership:
USD 23,430
Availability confirmation required.

Gary (KGYY) to Jackson (KJAC)

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March 1, 2026 - March 1, 2026
6 passengers
2.8 hours in flight
Honda Aircraft HA-420 HondaJet (Entry level jet (VLJ))
Aircraft photos: 2
Honda Aircraft HA-420 HondaJet empty leg from Gary (KGYY) to Jackson (KJAC) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 22,000
Price without Membership:
USD 24,200
Availability confirmation required.

Providenciales Island (MBPV) to Gary (KGYY)

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February 28, 2026 - February 28, 2026
10 passengers
3.0 hours in flight
Bombardier Challenger 300 (Super midsize jet)
Aircraft photos: 2
Bombardier Challenger 300 empty leg from Providenciales Island (MBPV) to Gary (KGYY) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 14,960
Price without Membership:
USD 16,460
Availability confirmation required.

Road Town (TUPJ) to Gary (KGYY)

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February 27, 2026 - February 28, 2026
10 passengers
3.9 hours in flight
Challenger 300 (Super midsize jet)
Aircraft photos: 2
Challenger 300 empty leg from Road Town (TUPJ) to Gary (KGYY) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 17,730
Price without Membership:
USD 19,503
Availability confirmation required.

Jackson (KJAC) to Gary (KGYY)

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February 26, 2026 - February 26, 2026
6 passengers
2.8 hours in flight
Honda Aircraft HA-420 HondaJet (Entry level jet (VLJ))
Aircraft photos: 2
Honda Aircraft HA-420 HondaJet empty leg from Jackson (KJAC) to Gary (KGYY) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 22,000
Price without Membership:
USD 24,200
Availability confirmation required.

New Bedford (KEWB) to Gary (KGYY)

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February 23, 2026 - February 23, 2026
9 passengers
1.7 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from New Bedford (KEWB) to Gary (KGYY) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 17,710
Price without Membership:
USD 19,480
Availability confirmation required.

New Bedford (KEWB) to Gary (KGYY)

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February 23, 2026 - February 23, 2026
9 passengers
1.7 hours in flight
CE-560-XLS (CITATION XLS) (Midsize jet)
Aircraft photos: 2
CE-560-XLS (CITATION XLS) empty leg from New Bedford (KEWB) to Gary (KGYY) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 17,710
Price without Membership:
USD 19,480
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.