Discover exceptional savings with our exclusive empty leg opportunities. These one-way repositioning flights allow you to enjoy the luxury of a private charter at a fraction of the usual cost. Explore our regularly updated list of empty legs departing from or arriving in the Chicago area.
Chicago (MDW / KMDW) to Marco Island (MRK / KMKY)
Price without Membership:
USD 15,400
Price with Membership:
USD 14,000
Price including all taxes & fees
March 19, 2025 – March 19, 2025
Price without Membership:
USD 15,400
Price with Membership:
USD 14,000
Including all taxes & fees
Chicago (MDW / KMDW) to Marco Island (MRK / KMKY)
Price without Membership:
USD 15,400
Price with Membership:
USD 14,000
Price including all taxes & fees
March 20, 2025 – March 20, 2025
Price without Membership:
USD 15,400
Price with Membership:
USD 14,000
Including all taxes & fees
New Orleans (NEW / KNEW) to Chicago (MDW / KMDW)
Price without Membership:
USD 13,200
Price with Membership:
USD 12,000
Price including all taxes & fees
March 24, 2025 – March 24, 2025
Price without Membership:
USD 13,200
Price with Membership:
USD 12,000
Including all taxes & fees
Chicago (MDW / KMDW) to Marco Island (MRK / KMKY)
Price without Membership:
USD 15,400
Price with Membership:
USD 14,000
Price including all taxes & fees
March 26, 2025 – March 26, 2025
Price without Membership:
USD 15,400
Price with Membership:
USD 14,000
Including all taxes & fees
Chicago (MDW / KMDW) to New Orleans (NEW / KNEW)
Price without Membership:
USD 13,200
Price with Membership:
USD 12,000
Price including all taxes & fees
March 27, 2025 – March 27, 2025
Price without Membership:
USD 13,200
Price with Membership:
USD 12,000
Including all taxes & fees
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We provide access to all the key airports in and around Chicago, ensuring you reach your destination efficiently and comfortably.
Longest Runway: 6,522 feet
Location: Chicago, IL
Ideal for: Access to downtown Chicago and surrounding suburbs
Available FBOs
— Atlantic Aviation
Address: 6150 South Laramie Avenue, Chicago, IL 60638, United States
Phone Number: +1 773-582-5720
Email: mdwfrontdesk@atlanticaviation.com
— Signature Aviation
Address: 5821 South Central Avenue, Chicago, IL 60638, United States
Phone Number: +1 773-767-4400
Email: mdw@signatureflight.com
Longest Runway: 5,001 feet
Location: Wheeling, IL
Ideal for: Northern suburbs and business districts
Available FBOs
— Atlantic Aviation
Address: 1011 S Wolf Rd, Wheeling, IL 60090, United States
Phone Number: +1 847-808-0812
Email: pwkfrontdesk@atlanticaviation.com
— Hawthorne Global Aviation Services
Address: 1120 S Milwaukee Ave, Chicago/Wheeling, IL 60090, United States
Phone Number: +1 847-325-0566
Email: kpwk@hawthorne.aero
— Signature Aviation
Address: 1100 S Milwaukee Ave, Wheeling, IL 60090, United States
Phone Number: +1 847-537-1200
Email: pwk@signatureflight.com
— Trego Dugan Aviation
Address: 1011 South Wolf Rd, Chicago/Wheeling, IL 60090, United States
Phone Number: +1 877-359-8356
Longest Runway: 7,571 feet
Location: West Chicago, IL
Ideal for: Western suburbs and corporate headquarters
Available FBOs
— DuPage Flight Center
Address: 2700 International Dr, Chicago/West Chicago, IL 60185, United States
Phone Number: +1 630-208-5600
Email: dfcfuel@dupageairport.com
Longest Runway: 6,600 feet
Location: Kenosha, WI
Ideal for: Northern Illinois and Southern Wisconsin
Available FBOs
— AVP/Kenosha Aviation LLC
Address: 9894 52nd St., Kenosha, WI 53144-7425, United States
Phone Number: +1 262-605-0474
Email: avpkenoshaaviation@gmail.com
— Stein's Aircraft Services, LLC
Address: 4222 91st Ave, Kenosha, WI 53144, United States
Phone Number: +1 262-597-1087
Email: info@stein.aero
While Chicago O'Hare International Airport (ORD/KORD) is one of the world's busiest airports, it is typically not used for private charters due to heavy commercial traffic. However, we can accommodate flights to other regional airports upon request, offering greater flexibility throughout the Chicago region.
— BE-200 (SUPER KING AIR)
— BE-300B (SUPER KING AIR)
— CE-208B (GRAND CARAVAN)
— PC-12-45 (PILATUS)
— DA-2000 (FALCON 2000)
— G-500 (G-500)
— G-IV (GULFSTREAM IV)
— CL-604 (CHALLENGER 604)
— DA-7X (FALCON 7X)
— G-650
— DA-2000 (FALCON 2000)
— DA-900EX EASY (FALCON 900EX EASY)
— DA-900EX EASY (FALCON 900EX EASY)
— BD-700-1A10 (GLOBAL EXPRESS)
— DA-2000 (FALCON 2000)
— CL-604 (CHALLENGER 604)
— DA-7X (FALCON 7X)
— CE-680 (CITATION SOVEREIGN)
— G-280
— CE-680 (CITATION SOVEREIGN)
— CE-680 (CITATION SOVEREIGN)
— CE-680 (CITATION SOVEREIGN)
— CE-680 (CITATION SOVEREIGN)
— HS-125-4000 (HAWKER 4000)
— BD-100-1A10 (CHALLENGER 300)
— LR-45 (LEARJET 45)
— HS-125-800XP (HAWKER 800XP)
— HS-125-850XP (HAWKER)
— HS-125-800XP (HAWKER 800XP)
— HS-125-850XP (HAWKER)
— LR-45 (LEARJET 45)
— LR-45 (LEARJET 45)
— CE-560-XL (CITATION EXCEL)
— IAI-1125 (WESTWIND ASTRA)
— IAI-1125 (WESTWIND ASTRA)
— CE-650 (CITATION III)
— CE-560-XLS+ (Citation XLS+)
— EMB-545 (LEGACY 450)
— LR-45 (LEARJET 45)
— CE-560-XL (CITATION EXCEL)
— CE-525 (CITATION JET 1)
— CE-525A (CITATION JET 2)
— CE-525B (CITATION JET 3)
— CE-525C (CITATION JET 4)
— CE-525 (CITATION JET 1)
— EMB-505 (PHENOM 300)
— CE-560 (CITATION V)
— CE-560 (CITATION V)
— PC-24
— CE-560 (CITATION V)
— BE-400A (BEECHJET)
— CE-525 (CITATION JET 1)
— CE-525 (CITATION JET 1)
— CE-550-B (CITATION BRAVO)
— CE-550 (CITATION II)
— CE-525B (CITATION JET 3)
— BE-1900 (COMMUTER)
— BE-1900C (COMMUTER)
Personalized Itineraries
Fly on your schedule with customized charter jet services
Luxury Fleet
Choose from a range of modern, high-end aircraft
Competitive Pricing
Benefit from our attractive rates and empty leg options
Exceptional Service
Enjoy a seamless travel experience with our dedicated team
TriStar 24/7 Call Center
E-Mail Support
TriStar Charters & Concierge arranges flights on behalf of our clients with FAA Certified FAR Part 135 direct air carriers that exercise full operational control of charter flights at all times. All flights purchased on our platform will be operated by FAR Part 135 direct air carriers that have been certified to provide service for the TriStar Charters & Concierge company clients and that meet all FAA safety standards. Your itinerary will clearly state the name of the certified operator conducting your flight.