Empty leg flights available Chicago Executive Airport (KPWK)

Chicago/prospect Heights/wheeling, Illinois, 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

Chicago/Prospect Heights/Wheeling (KPWK) to Pensacola (KPNS)

View details

March 25, 2026 - March 26, 2026

16 passengers

1.4 hours in flight

Gulfstream G V (Ultra long range)

Aircraft photos: 2

Gulfstream G V empty leg from Chicago/Prospect Heights/Wheeling (KPWK) to Pensacola (KPNS) photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 11,850

Price without Membership:

USD 13,030

Availability confirmation required.

St. John's (TAPA) to Chicago/Prospect Heights/Wheeling (KPWK)

View details

March 19, 2026 - March 19, 2026

16 passengers

4.0 hours in flight

Gulfstream G V (Ultra long range)

Aircraft photos: 2

Gulfstream G V empty leg from St. John's (TAPA) to Chicago/Prospect Heights/Wheeling (KPWK) photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 34,030

Price without Membership:

USD 37,430

Availability confirmation required.

Chicago/Prospect Heights/Wheeling (KPWK) to Teterboro (KTEB)

View details

April 27, 2026 - April 27, 2026

14 passengers

1.2 hours in flight

Gulfstream G450 (Heavy jet)

Aircraft photos: 2

Gulfstream G450 empty leg from Chicago/Prospect Heights/Wheeling (KPWK) to Teterboro (KTEB) photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 10,700

Price without Membership:

USD 11,770

Availability confirmation required.

Teterboro (KTEB) to Chicago/Prospect Heights/Wheeling (KPWK)

View details

April 22, 2026 - April 22, 2026

14 passengers

1.2 hours in flight

Gulfstream G450 (Heavy jet)

Aircraft photos: 2

Gulfstream G450 empty leg from Teterboro (KTEB) to Chicago/Prospect Heights/Wheeling (KPWK) photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 10,700

Price without Membership:

USD 11,770

Availability confirmation required.

Chicago/Prospect Heights/Wheeling (KPWK) to Baltimore (KBWI)

View details

March 13, 2026 - March 13, 2026

8 passengers

1.2 hours in flight

Cessna Citation XLS (Midsize jet)

Aircraft photos: 2

Cessna Citation XLS empty leg from Chicago/Prospect Heights/Wheeling (KPWK) to Baltimore (KBWI) photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 7,690

Price without Membership:

USD 8,460

Availability confirmation required.

Teterboro (KTEB) to Chicago/Prospect Heights/Wheeling (KPWK)

View details

February 27, 2026 - February 27, 2026

8 passengers

1.4 hours in flight

Beechcraft Hawker 900XP (Midsize jet)

Aircraft photos: 2

Beechcraft Hawker 900XP empty leg from Teterboro (KTEB) to Chicago/Prospect Heights/Wheeling (KPWK) photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 11,220

Price without Membership:

USD 12,340

Availability confirmation required.

Fort Myers (KFMY) to Chicago/Prospect Heights/Wheeling (KPWK)

View details

February 24, 2026 - February 24, 2026

9 passengers

2.3 hours in flight

Embraer Praetor 500 (Super midsize jet)

Aircraft photos: 2

Embraer Praetor 500 empty leg from Fort Myers (KFMY) to Chicago/Prospect Heights/Wheeling (KPWK) photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 23,820

Price without Membership:

USD 26,200

Availability confirmation required.

Chicago/Prospect Heights/Wheeling (KPWK) to Pontiac (KPTK)

View details

February 22, 2026 - February 22, 2026

12 passengers

1.0 hours in flight

Bombardier Challenger 604 (Heavy jet)

Aircraft photos: 2

Bombardier Challenger 604 empty leg from Chicago/Prospect Heights/Wheeling (KPWK) to Pontiac (KPTK) 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/Prospect Heights/Wheeling (KPWK) to Telluride (KTEX)

View details

February 22, 2026 - February 22, 2026

8 passengers

2.2 hours in flight

Cessna Citation XLS+ (Midsize jet)

Aircraft photos: 2

Cessna Citation XLS+ empty leg from Chicago/Prospect Heights/Wheeling (KPWK) to Telluride (KTEX) photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 22,840

Price without Membership:

USD 25,120

Availability confirmation required.

Chicago/Prospect Heights/Wheeling (KPWK) to Naples (KAPF)

View details

February 19, 2026 - February 21, 2026

8 passengers

2.3 hours in flight

Cessna Citation Ultra (Light jet)

Aircraft photos: 2

Cessna Citation Ultra empty leg from Chicago/Prospect Heights/Wheeling (KPWK) to Naples (KAPF) photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 12,000

Price without Membership:

USD 13,200

Availability confirmation required.

Chicago/Prospect Heights/Wheeling (KPWK) to Bozeman (KBZN)

View details

February 21, 2026 - February 21, 2026

14 passengers

2.0 hours in flight

Gulfstream G450 (Heavy jet)

Aircraft photos: 2

Gulfstream G450 empty leg from Chicago/Prospect Heights/Wheeling (KPWK) to Bozeman (KBZN) photo 1

1 / 2

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.

Chicago/Prospect Heights/Wheeling (KPWK) to Pontiac (KPTK)

View details

February 20, 2026 - February 20, 2026

8 passengers

1.0 hours in flight

Cessna Citation Excel (Midsize jet)

Aircraft photos: 2

Cessna Citation Excel empty leg from Chicago/Prospect Heights/Wheeling (KPWK) to Pontiac (KPTK) 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.

Teterboro (KTEB) to Chicago/Prospect Heights/Wheeling (KPWK)

View details

February 25, 2026 - February 25, 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/Prospect Heights/Wheeling (KPWK) photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 12,260

Price without Membership:

USD 13,480

Availability confirmation required.

KPWK to KTEB

View details

February 18, 2026 - February 18, 2026

14 passengers

1.2 hours in flight

Gulfstream G450 (Heavy jet)

Aircraft photos: 2

Gulfstream G450 empty leg from KPWK to KTEB photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 12,630

Price without Membership:

USD 13,893

Availability confirmation required.

KTEB to KPWK

View details

February 14, 2026 - February 14, 2026

14 passengers

1.2 hours in flight

Gulfstream G450 (Heavy jet)

Aircraft photos: 2

Gulfstream G450 empty leg from KTEB to KPWK photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 7,120

Price without Membership:

USD 7,832

Availability confirmation required.

KSGR to KPWK

View details

February 04, 2026 - February 07, 2026

8 passengers

1.9 hours in flight

Cessna Citation Excel (Midsize jet)

Aircraft photos: 2

Cessna Citation Excel empty leg from KSGR to KPWK photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 11,250

Price without Membership:

USD 12,375

Availability confirmation required.

KPWK to KTEB

View details

February 03, 2026 - February 03, 2026

13 passengers

1.4 hours in flight

Legacy 600 (Heavy jet)

Aircraft photos: 2

Legacy 600 empty leg from KPWK to KTEB photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 14,220

Price without Membership:

USD 15,642

Availability confirmation required.

KTEB to KPWK

View details

January 27, 2026 - January 27, 2026

13 passengers

1.4 hours in flight

Legacy 600 (Heavy jet)

Aircraft photos: 2

Legacy 600 empty leg from KTEB to KPWK photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 15,460

Price without Membership:

USD 17,006

Availability confirmation required.

KPWK to KARV

View details

January 19, 2026 - January 19, 2026

9 passengers

Flight time n/a

Praetor 500 (Super midsize jet)

Aircraft photos: 2

Praetor 500 empty leg from KPWK to KARV photo 1

1 / 2

What is TriStar Membership?

Learn how membership unlocks better pricing and priority support.

Price with Membership:

USD 5,490

Price without Membership:

USD 6,039

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.