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Private Jet Charter
from Chicago
Chicago Midway Airport (KMDW)

85+ aircraft available at Chicago Midway Airport. Light jets from $9,200 - ultra-long-range to any destination worldwide. Quotes in 60 minutes. No commitment required.

Get a Quote → Ground Transport
85+
Jets Available
60min
Quote Time
9+
Broker Network
24/7
Availability
Top Routes from Chicago

Popular Flight Routes
from KMDW

Current all-in private charter pricing from Chicago Midway Airport. Estimates only; the operator or broker you book with sets the final price. Prices fluctuate - request a live quote for exact figures.

FromEst. PriceDestinationFlight Time
Chicago KMDW$11,000NYC2hr
Chicago KMDW$16,000Miami2.5hr
Chicago KMDW$9,200Dallas1.5hr
Chicago KMDW$24,000LA4hr
About KMDW

Why Fly Private from
Chicago Midway Airport

Chicago Midway Airport is one of the premier private aviation facilities in IL. Unlike commercial airports, KMDW offers dedicated FBO terminals, zero TSA lines, and the ability to depart within 2 hours of booking. Port access: Port of Chicago. The airport serves Chicago and the surrounding metro area with 85+ aircraft based on-site.

Private jet charter from KMDW offers access to all aircraft categories - from economical very light jets ideal for 1-3 passengers on short hops, to ultra-long-range Gulfstream G650s and Global 7500s capable of nonstop intercontinental routes. LetsLeaveNow links to third-party charter brokers and operators and may earn a commission when you book through those links; the operator you book with sets the final price.

Aircraft Available at KMDW

Very Light Jet
Phenom 100E / Eclipse 550
1-3 passengers. Ideal for short hops under 3 hours. Most economical option for solo executives.
$2,990/hr
Charter →
Midsize Jet
Citation XLS+ / Hawker 800XP
4-8 passengers. Stand-up cabin, full baggage. Perfect for domestic routes under 5 hours.
$6,240/hr
Charter →
Heavy Jet
Gulfstream G550 / Global 6000
8-16 passengers. Full stand-up cabin, sleeping berths, international range. For long-haul premium travel.
$14,300/hr
Charter →
FBO to Hotel

Ground Transport from
KMDW

LetsLeaveNow coordinates seamless ground transport from Chicago Midway Airport to your hotel, cruise terminal, or final destination. Our black car and charter bus network covers Chicago and the surrounding region.

🚘 Executive Sedan
Mercedes S-Class / BMW 7-Series
1-3 passengers. Meet & greet at FBO. Professional driver, complimentary water and wifi.
$195/transfer
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🚐 Executive Van
Mercedes Sprinter VIP
Up to 14 passengers. Captain seating, privacy glass, WiFi. Ideal for corporate jet groups.
$295/transfer
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🚌 Charter Bus
55-Passenger Motorcoach
Large groups, corporate events, or cruise port shuttles. BusBrother certified operator.
$185/hr
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Other Airports

Other Private Aviation
Hubs Near Chicago

✈ Teterboro, NJ✈ White Plains, NY✈ Miami, FL✈ Fort Lauderdale, FL✈ Van Nuys, CA✈ Las Vegas, NV
FAQ

Common Questions About
Private Jets from Chicago

How much does it cost to charter a private jet from KMDW? +
Private jet charters from Chicago Midway Airport start around $$11,000 for short-hop routes on a very light jet. Midsize jets run $6,000-$12,000 for typical domestic routes, while heavy jets for coast-to-coast start around $22,000. Prices shown are estimates; the licensed operator or broker you book with sets the final price.
How quickly can I depart from KMDW? +
Most private jet bookings from KMDW can be ready to fly within 2-4 hours of confirmation. With pre-identified aircraft and expedited FBO clearance, same-day departures are standard. We've arranged flights with as little as 90 minutes notice.
What FBOs are available at Chicago Midway Airport? +
Chicago Midway Airport is served by multiple FBO operators offering private lounges, fuel, catering, and hangar services. Our brokers will select the optimal FBO based on your aircraft type and requirements.
Can you arrange ground transport from the FBO? +
Yes. LetsLeaveNow coordinates door-to-door travel. Black car pickup, Sprinter vans for groups, and charter buses are all available from KMDW. Our ground transport network covers Chicago and the surrounding region 24/7.
Are there empty leg deals from KMDW? +
Yes - empty leg availability from Chicago Midway Airport changes daily. These are repositioning flights that sell for 50-75% below normal charter rates. Check our Private Jets page for current empty legs, or sign up for deal alerts to be notified when one becomes available from KMDW.