EMPTYLEG STORE
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Empty leg flights available Chicago Midway International Airport (KMDW)

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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Chicago (KMDW) to Concord (KJQF)

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February 26, 2026 - February 26, 2026
8 passengers
1.1 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from Chicago (KMDW) to Concord (KJQF) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 8,500
Price without Membership:
USD 9,350
Availability confirmation required.

Syracuse (KSYR) to Chicago (KMDW)

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February 24, 2026 - February 24, 2026
7 passengers
1.1 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from Syracuse (KSYR) to Chicago (KMDW) 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.

Lincoln (KLNK) to Chicago (KMDW)

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February 27, 2026 - February 27, 2026
8 passengers
1.0 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from Lincoln (KLNK) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 7,200
Price without Membership:
USD 7,920
Availability confirmation required.

Syracuse (KSYR) to Chicago (KMDW)

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February 24, 2026 - February 24, 2026
8 passengers
1.1 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from Syracuse (KSYR) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 13,000
Price without Membership:
USD 14,300
Availability confirmation required.

Syracuse (KSYR) to Chicago (KMDW)

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February 24, 2026 - February 24, 2026
7 passengers
1.1 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from Syracuse (KSYR) to Chicago (KMDW) 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.

Syracuse (KSYR) to Chicago (KMDW)

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February 24, 2026 - February 24, 2026
8 passengers
1.1 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from Syracuse (KSYR) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 13,000
Price without Membership:
USD 14,300
Availability confirmation required.

Chicago (KMDW) to Farmingdale (KFRG)

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February 22, 2026 - February 22, 2026
13 passengers
1.4 hours in flight
Embraer Legacy 600 (Heavy jet)
Aircraft photos: 2
Embraer Legacy 600 empty leg from Chicago (KMDW) to Farmingdale (KFRG) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 12,180
Price without Membership:
USD 13,400
Availability confirmation required.

Sarasota/Bradenton (KSRQ) to Chicago (KMDW)

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February 21, 2026 - February 22, 2026
8 passengers
2.3 hours in flight
Beechcraft Hawker 400XP (Light jet)
Aircraft photos: 2
Beechcraft Hawker 400XP empty leg from Sarasota/Bradenton (KSRQ) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 14,000
Price without Membership:
USD 15,400
Availability confirmation required.

Teterboro (KTEB) to Chicago (KMDW)

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February 20, 2026 - February 21, 2026
12 passengers
1.2 hours in flight
Gulfstream G IV SP (Heavy jet)
Aircraft photos: 2
Gulfstream G IV SP empty leg from Teterboro (KTEB) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 9,950
Price without Membership:
USD 10,950
Availability confirmation required.

Farmingdale (KFRG) to Chicago (KMDW)

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February 20, 2026 - February 20, 2026
13 passengers
1.4 hours in flight
Embraer Legacy 600 (Heavy jet)
Aircraft photos: 2
Embraer Legacy 600 empty leg from Farmingdale (KFRG) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 12,180
Price without Membership:
USD 13,400
Availability confirmation required.

Chicago (KMDW) to Indianapolis (KTYQ)

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February 19, 2026 - February 19, 2026
7 passengers
1.0 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from Chicago (KMDW) to Indianapolis (KTYQ) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 3,000
Price without Membership:
USD 3,300
Availability confirmation required.

Chicago (KMDW) to Apalachicola (KAAF)

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February 05, 2026 - February 05, 2026
8 passengers
1.9 hours in flight
Hawker 400XP (Light jet)
Aircraft photos: 2
Hawker 400XP empty leg from Chicago (KMDW) to Apalachicola (KAAF) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 14,000
Price without Membership:
USD 15,400
Availability confirmation required.

Chicago (KMDW) to Marco Island (KMKY)

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February 03, 2026 - February 03, 2026
8 passengers
2.5 hours in flight
Beechjet 400A (Light jet)
Aircraft photos: 1
Beechjet 400A empty leg from Chicago (KMDW) to Marco Island (KMKY) photo 1
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 14,000
Price without Membership:
USD 15,400
Availability confirmation required.

Cleveland (KCLE) to Chicago (KMDW)

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January 29, 2026 - January 29, 2026
7 passengers
1.0 hours in flight
Learjet 40XR (Super light jet)
Aircraft photos: 2
Learjet 40XR empty leg from Cleveland (KCLE) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 3,540
Price without Membership:
USD 3,894
Availability confirmation required.

Chicago (KMDW) to Stuart (KSUA)

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January 27, 2026 - January 27, 2026
8 passengers
2.4 hours in flight
Beechjet 400A (Light jet)
Aircraft photos: 1
Beechjet 400A empty leg from Chicago (KMDW) to Stuart (KSUA) photo 1
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 14,000
Price without Membership:
USD 15,400
Availability confirmation required.

KMDW to KX07

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January 26, 2026 - January 26, 2026
8 passengers
2.3 hours in flight
Hawker 400XP (Light jet)
Aircraft photos: 2
Hawker 400XP empty leg from KMDW to KX07 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.

Fort Myers (KRSW) to Chicago (KMDW)

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January 23, 2026 - January 23, 2026
8 passengers
2.5 hours in flight
Hawker 400XP (Light jet)
Aircraft photos: 2
Hawker 400XP empty leg from Fort Myers (KRSW) to Chicago (KMDW) 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 (KMDW) to Marco Island (KMKY)

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January 20, 2026 - January 20, 2026
8 passengers
2.5 hours in flight
Hawker 400XP (Light jet)
Aircraft photos: 2
Hawker 400XP empty leg from Chicago (KMDW) to Marco Island (KMKY) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 14,000
Price without Membership:
USD 15,400
Availability confirmation required.

White Plains (KHPN) to Chicago (KMDW)

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January 20, 2026 - January 20, 2026
8 passengers
1.6 hours in flight
Hawker 400XP (Light jet)
Aircraft photos: 2
Hawker 400XP empty leg from White Plains (KHPN) to Chicago (KMDW) 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 (KMDW) to Farmingdale (KFRG)

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January 19, 2026 - January 19, 2026
7 passengers
1.4 hours in flight
Learjet 60 (Midsize jet)
Aircraft photos: 1
Learjet 60 empty leg from Chicago (KMDW) to Farmingdale (KFRG) photo 1
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 6,210
Price without Membership:
USD 6,831
Availability confirmation required.

Chicago (KMDW) to Cleveland (KCLE)

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January 18, 2026 - January 18, 2026
7 passengers
1.0 hours in flight
Learjet 40XR (Super light jet)
Aircraft photos: 2
Learjet 40XR empty leg from Chicago (KMDW) to Cleveland (KCLE) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 5,990
Price without Membership:
USD 6,589
Availability confirmation required.

Venice (KVNC) to Chicago (KMDW)

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January 18, 2026 - January 18, 2026
8 passengers
2.4 hours in flight
Hawker 400XP (Light jet)
Aircraft photos: 2
Hawker 400XP empty leg from Venice (KVNC) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 14,000
Price without Membership:
USD 15,400
Availability confirmation required.

Lynchburg (KLYH) to Chicago (KMDW)

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January 17, 2026 - January 17, 2026
7 passengers
1.0 hours in flight
Learjet 40XR (Super light jet)
Aircraft photos: 2
Learjet 40XR empty leg from Lynchburg (KLYH) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 7,990
Price without Membership:
USD 8,789
Availability confirmation required.

St Petersburg-Clearwater (KPIE) to Chicago (KMDW)

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January 15, 2026 - January 15, 2026
8 passengers
2.1 hours in flight
Falcon 2000EX EASy (Heavy jet)
Aircraft photos: 2
Falcon 2000EX EASy empty leg from St Petersburg-Clearwater (KPIE) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 19,650
Price without Membership:
USD 21,615
Availability confirmation required.

Farmingdale (KFRG) to Chicago (KMDW)

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January 15, 2026 - January 15, 2026
7 passengers
1.4 hours in flight
Learjet 60 (Midsize jet)
Aircraft photos: 1
Learjet 60 empty leg from Farmingdale (KFRG) to Chicago (KMDW) photo 1
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 6,780
Price without Membership:
USD 7,458
Availability confirmation required.

Boca Raton (KBCT) to Chicago (KMDW)

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January 14, 2026 - January 15, 2026
7 passengers
2.2 hours in flight
Learjet 60 (Midsize jet)
Aircraft photos: 1
Learjet 60 empty leg from Boca Raton (KBCT) to Chicago (KMDW) photo 1
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 16,300
Price without Membership:
USD 17,930
Availability confirmation required.

Fort Lauderdale (KFXE) to Chicago (KMDW)

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January 14, 2026 - January 15, 2026
7 passengers
2.2 hours in flight
Learjet 60 (Midsize jet)
Aircraft photos: 1
Learjet 60 empty leg from Fort Lauderdale (KFXE) to Chicago (KMDW) photo 1
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 13,000
Price without Membership:
USD 14,300
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.