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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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Cleveland (KRZR) to Chicago (KMDW)

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March 26, 2026 - March 26, 2026
12 passengers
1.0 hours in flight
Dassault Falcon 900B (Heavy jet)
Aircraft photos: 2
Dassault Falcon 900B empty leg from Cleveland (KRZR) to Chicago (KMDW) 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.

Cleveland (KRZR) to Chicago (KMDW)

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March 27, 2026 - March 27, 2026
12 passengers
1.0 hours in flight
Dassault Falcon 900B (Heavy jet)
Aircraft photos: 2
Dassault Falcon 900B empty leg from Cleveland (KRZR) to Chicago (KMDW) 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.

Teterboro (KTEB) to Chicago (KMDW)

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March 27, 2026 - March 27, 2026
10 passengers
1.5 hours in flight
Bombardier Challenger 650 (Heavy jet)
Aircraft photos: 2
Bombardier Challenger 650 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 12,570
Price without Membership:
USD 13,830
Availability confirmation required.

White Plains (KHPN) to Chicago (KMDW)

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April 5, 2026 - April 6, 2026
8 passengers
1.6 hours in flight
Beechcraft Hawker 400XP (Light jet)
Aircraft photos: 2
Beechcraft 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 14,000
Price without Membership:
USD 15,400
Availability confirmation required.

Chicago (KMDW) to Dallas (KDAL)

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April 6, 2026 - April 6, 2026
7 passengers
1.6 hours in flight
Cessna Citation Ultra (Light jet)
Aircraft photos: 2
Cessna Citation Ultra empty leg from Chicago (KMDW) to Dallas (KDAL) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 8,000
Price without Membership:
USD 8,800
Availability confirmation required.

Houston (KHOU) to Chicago (KMDW)

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April 7, 2026 - April 7, 2026
7 passengers
1.9 hours in flight
Cessna Citation V (Light jet)
Aircraft photos: 2
Cessna Citation V empty leg from Houston (KHOU) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 7,400
Price without Membership:
USD 8,140
Availability confirmation required.

Scottsdale (KSDL) to Chicago (KMDW)

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April 23, 2026 - April 23, 2026
8 passengers
2.6 hours in flight
Bombardier Challenger 350 (Super midsize jet)
Aircraft photos: 2
Bombardier Challenger 350 empty leg from Scottsdale (KSDL) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 27,640
Price without Membership:
USD 30,410
Availability confirmation required.

Chicago (KMDW) to Scottsdale (KSDL)

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May 8, 2026 - May 8, 2026
9 passengers
2.6 hours in flight
Bombardier Challenger 350 (Super midsize jet)
Aircraft photos: 2
Bombardier Challenger 350 empty leg from Chicago (KMDW) to Scottsdale (KSDL) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 27,640
Price without Membership:
USD 30,410
Availability confirmation required.

Scottsdale (KSDL) to Chicago (KMDW)

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May 11, 2026 - May 11, 2026
9 passengers
2.6 hours in flight
Bombardier Challenger 350 (Super midsize jet)
Aircraft photos: 2
Bombardier Challenger 350 empty leg from Scottsdale (KSDL) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 27,640
Price without Membership:
USD 30,410
Availability confirmation required.

Groton (New London) (KGON) to Chicago (KMDW)

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May 11, 2026 - May 15, 2026
8 passengers
1.6 hours in flight
Cessna Citation Excel (Midsize jet)
Aircraft photos: 2
Cessna Citation Excel empty leg from Groton (New London) (KGON) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 11,500
Price without Membership:
USD 12,650
Availability confirmation required.

Chicago (KMDW) to Teterboro (KTEB)

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June 5, 2026 - June 5, 2026
14 passengers
1.2 hours in flight
Gulfstream G IV SP (Heavy jet)
Aircraft photos: 2
Gulfstream G IV SP empty leg from Chicago (KMDW) to Teterboro (KTEB) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 10,580
Price without Membership:
USD 11,630
Availability confirmation required.

Teterboro (KTEB) to Chicago (KMDW)

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June 8, 2026 - June 8, 2026
14 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 10,580
Price without Membership:
USD 11,630
Availability confirmation required.

Toronto (CYYZ) to Chicago (KMDW)

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July 17, 2026 - July 18, 2026
7 passengers
1.0 hours in flight
Embraer Phenom 300 (Super light jet)
Aircraft photos: 2
Embraer Phenom 300 empty leg from Toronto (CYYZ) to Chicago (KMDW) 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.

West Palm Beach (KPBI) to Chicago (KMDW)

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March 23, 2026 - March 25, 2026
8 passengers
2.4 hours in flight
Cessna Citation CJ3 (Light jet)
Aircraft photos: 2
Cessna Citation CJ3 empty leg from West Palm Beach (KPBI) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 10,000
Price without Membership:
USD 10,990
Availability confirmation required.

Chicago (KMDW) to Akron (KCAK)

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March 22, 2026 - March 22, 2026
7 passengers
1.0 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 1
Bombardier Learjet 60 empty leg from Chicago (KMDW) to Akron (KCAK) photo 1
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 4,800
Price without Membership:
USD 5,280
Availability confirmation required.

Chicago (KMDW) to Austin (KAUS)

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March 19, 2026 - March 20, 2026
9 passengers
1.8 hours in flight
Cessna Citation VI (Midsize jet)
Aircraft photos: 2
Cessna Citation VI empty leg from Chicago (KMDW) to Austin (KAUS) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 19,160
Price without Membership:
USD 21,070
Availability confirmation required.

Chicago (KMDW) to Dayton (KDAY)

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March 19, 2026 - March 19, 2026
8 passengers
1.0 hours in flight
Cessna Citation Bravo (Light jet)
Aircraft photos: 2
Cessna Citation Bravo empty leg from Chicago (KMDW) to Dayton (KDAY) 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.

Chicago (KMDW) to Atlanta (KRYY)

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March 18, 2026 - March 18, 2026
12 passengers
1.2 hours in flight
Bombardier Challenger 605 (Heavy jet)
Aircraft photos: 2
Bombardier Challenger 605 empty leg from Chicago (KMDW) to Atlanta (KRYY) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 33,150
Price without Membership:
USD 36,460
Availability confirmation required.

San Antonio (KSAT) to Chicago (KMDW)

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March 18, 2026 - March 18, 2026
7 passengers
2.0 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from San Antonio (KSAT) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 13,300
Price without Membership:
USD 14,630
Availability confirmation required.

San Antonio (KSAT) to Chicago (KMDW)

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March 18, 2026 - March 18, 2026
8 passengers
2.0 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from San Antonio (KSAT) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 14,400
Price without Membership:
USD 15,840
Availability confirmation required.

Miami (KOPF) to Chicago (KMDW)

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March 18, 2026 - March 18, 2026
7 passengers
2.2 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 1
Bombardier Learjet 60 empty leg from Miami (KOPF) 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.

Miami (KOPF) to Chicago (KMDW)

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March 18, 2026 - March 18, 2026
8 passengers
2.2 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from Miami (KOPF) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 17,600
Price without Membership:
USD 19,360
Availability confirmation required.

Asheville (KAVL) to Chicago (KMDW)

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March 18, 2026 - March 18, 2026
7 passengers
1.0 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from Asheville (KAVL) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 9,000
Price without Membership:
USD 9,900
Availability confirmation required.

Asheville (KAVL) to Chicago (KMDW)

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March 18, 2026 - March 18, 2026
8 passengers
1.0 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from Asheville (KAVL) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 9,800
Price without Membership:
USD 10,780
Availability confirmation required.

Chicago (KMDW) to Austin (KAUS)

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March 17, 2026 - March 17, 2026
12 passengers
2.0 hours in flight
Bombardier Challenger 605 (Heavy jet)
Aircraft photos: 2
Bombardier Challenger 605 empty leg from Chicago (KMDW) to Austin (KAUS) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 17,150
Price without Membership:
USD 18,870
Availability confirmation required.

Asheville (KAVL) to Chicago (KMDW)

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March 17, 2026 - March 18, 2026
8 passengers
1.0 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from Asheville (KAVL) to Chicago (KMDW) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 9,700
Price without Membership:
USD 10,670
Availability confirmation required.

Louisville (KSDF) to Chicago (KMDW)

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March 14, 2026 - March 14, 2026
8 passengers
1.0 hours in flight
Cessna Citation Bravo (Light jet)
Aircraft photos: 2
Cessna Citation Bravo empty leg from Louisville (KSDF) to Chicago (KMDW) 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.

Chicago (KMDW) to West Palm Beach (KPBI)

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March 14, 2026 - March 16, 2026
8 passengers
2.4 hours in flight
Cessna Citation CJ3 (Light jet)
Aircraft photos: 2
Cessna Citation CJ3 empty leg from Chicago (KMDW) to West Palm Beach (KPBI) photo 1
1 / 2
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 10,000
Price without Membership:
USD 10,990
Availability confirmation required.

Chicago (KMDW) to Cleveland (KCGF)

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March 11, 2026 - March 11, 2026
7 passengers
1.0 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 1
Bombardier Learjet 60 empty leg from Chicago (KMDW) to Cleveland (KCGF) photo 1
What is TriStar Membership?
Learn how membership unlocks better pricing and priority support.
Price with Membership:
USD 4,800
Price without Membership:
USD 5,280
Availability confirmation required.

Chicago (KMDW) to Bedford (KBED)

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March 11, 2026 - March 11, 2026
8 passengers
1.6 hours in flight
Bombardier Learjet 60 (Midsize jet)
Aircraft photos: 2
Bombardier Learjet 60 empty leg from Chicago (KMDW) to Bedford (KBED) 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.

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.