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.

Want a quote for a specific route?

Tell us your itinerary and we’ll source live pricing.

Request a charter quote

Gary (KGYY) to Big Ambergris Cay (MBAC)

View details

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.

Sarasota/Bradenton (KSRQ) to Gary (KGYY)

View details

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 Road Town (TUPJ)

View details

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.

Gary (KGYY) to Naples (KAPF)

View details

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 Sarasota/Bradenton (KSRQ)

View details

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)

View details

March 15, 2026 - March 15, 2026

9 passengers

2.2 hours in flight

CE-560-XLS (CITATION XLS) (Midsize jet)

Aircraft photos: 2

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.

Atlanta (KPDK) to Gary (KGYY)

View details

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.

Pontiac (KPTK) to Gary (KGYY)

View details

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.

Providenciales Island (MBPV) to Gary (KGYY)

View details

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.

Gary (KGYY) to Jackson (KJAC)

View details

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.

Jackson (KJAC) to Gary (KGYY)

View details

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)

View details

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)

View details

February 23, 2026 - February 23, 2026

9 passengers

1.7 hours in flight

CE-560-XLS (CITATION XLS) (Midsize jet)

Aircraft photos: 2

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.

Gary (KGYY) to Eagle (KEGE)

View details

February 22, 2026 - February 23, 2026

8 passengers

2.1 hours in flight

Cessna Citation V (Light jet)

Aircraft photos: 2

Cessna Citation V empty leg from Gary (KGYY) to Eagle (KEGE) photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 16,220

Price without Membership:

USD 17,850

Availability confirmation required.

Farmingdale (KFRG) to Gary (KGYY)

View details

February 22, 2026 - February 22, 2026

8 passengers

1.5 hours in flight

Cessna Citation V (Light jet)

Aircraft photos: 2

Cessna Citation V empty leg from Farmingdale (KFRG) 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 16,870

Availability confirmation required.

Jackson (KJAC) to Gary (KGYY)

View details

February 20, 2026 - February 20, 2026

6 passengers

2.8 hours in flight

Honda Aircraft HA-420 HondaJet (Entry level jet (VLJ))

Aircraft photos: 2

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.

Sarasota/Bradenton (KSRQ) to Gary (KGYY)

View details

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 Atlanta (KPDK)

View details

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.

Naples (KAPF) to Gary (KGYY)

View details

February 23, 2026 - February 23, 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 11,060

Price without Membership:

USD 12,170

Availability confirmation required.

Road Town (TUPJ) to Gary (KGYY)

View details

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.

Fort Myers (KFMY) to Gary (KGYY)

View details

February 19, 2026 - February 19, 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 Fort Myers (KFMY) to Gary (KGYY) photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 9,920

Price without Membership:

USD 10,912

Availability confirmation required.

Gary (KGYY) to Fort Myers (KFMY)

View details

February 12, 2026 - February 12, 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 Fort Myers (KFMY) photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 11,430

Price without Membership:

USD 12,573

Availability confirmation required.

Gary (KGYY) to Toronto (CYYZ)

View details

February 10, 2026 - February 10, 2026

16 passengers

1.0 hours in flight

Gulfstream G V (Ultra long range)

Aircraft photos: 2

Gulfstream G V empty leg from Gary (KGYY) to Toronto (CYYZ) 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.

Hazleton (KHZL) to Gary (KGYY)

View details

February 01, 2026 - February 04, 2026

16 passengers

1.0 hours in flight

Gulfstream G V (Ultra long range)

Aircraft photos: 2

Gulfstream G V empty leg from Hazleton (KHZL) to Gary (KGYY) photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 29,120

Price without Membership:

USD 32,030

Availability confirmation required.

KJWN to KGYY

View details

January 19, 2026 - January 19, 2026

6 passengers

1.0 hours in flight

HA-420 HondaJet (Entry level jet (VLJ))

Aircraft photos: 2

HA-420 HondaJet empty leg from KJWN to 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.

KGYY to KJWN

View details

January 17, 2026 - January 17, 2026

6 passengers

1.0 hours in flight

HA-420 HondaJet (Entry level jet (VLJ))

Aircraft photos: 2

HA-420 HondaJet empty leg from KGYY to KJWN 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.

Eagle (KEGE) to Gary (KGYY)

View details

January 16, 2026 - January 16, 2026

9 passengers

2.1 hours in flight

CE-560-XLS (CITATION XLS) (Midsize jet)

Aircraft photos: 2

CE-560-XLS (CITATION XLS) empty leg from Eagle (KEGE) to Gary (KGYY) photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 13,840

Price without Membership:

USD 15,224

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.