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Fly Personal to Chicago, Illinois
Experience the ultimate convenience and comfort with a private charter flights directly into the Chicago Midway International Airport (MDW/KMDW) in Chicago, Illinois.
Private Service Flights Learn more
Travel with confidence to Chicago in our fleet of Citation CJ3 Jet aircraft. Our Citation CJ3 Jets are the newest standard in light jet comfort and performance, perfect for trips from Canada, the Northeast, and the Southeast US.
Should your trip require a larger cabin or longer range than our in-fleet Citation CJ3s, we will happily assist you with securing the ideal aircraft for your journey.
Tradewind offers the best availability in the industry for private service flights to Chicago, Illinois.
POPULAR ROUTES TO CHICAGO (MDW/KMDW)
IN THE CITATION CJ3:
| From | Flight Time |
| Austin, TX (AUS/KAUS) | 2 hours 25 minutes |
| Baton Rouge, LA (BTR/KBTR) | 2 hours 9 minutes |
| Boston, MA (BED/KBED, BOS/KBOS) | 2 hours 38 minutes |
| Montréal, Canada (YUL/CYUL) | 2 hours 21 minutes |
| Morristown, NJ (MMU/KMMU) | 2 hours 13 minutes |
| Nantucket, MA (ACK/KACK) | 2 hour 50 minutes |
| Philadelphia, PA (PHL/KPHL) | 2 hours 8 minutes |
| Teterboro, NJ (TEB/KTEB) | 2 hours 16 minutes |
| Westchester, NY (HPN/KHPN) | 2 hours 19 minutes |
Aircraft Options
The Tradewind Citation CJ3 Jet provides executive-configured seating for up to seven passengers and ample room for luggage. Enjoy complimentary WiFi on domestic flights in our Citation CJ3 Jets.
Should your trip require a larger cabin or longer range, Tradewind can secure the ideal aircraft for your journey. Our reach includes all the latest models of mid, super-mid, and heavy jets, including but not limited to Hawker, Gulfstream, Challenger, and Falcon aircraft.
Tradewind is a Part 135 operator of Pilatus PC-12 and Citation CJ3 Jet aircraft. Any travel arranged by Tradewind using a different aircraft type is neither owned nor operated by Tradewind.