$1000 Off Your First Southeast Flight or a Complimentary Flight Hour
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.
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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 Midwest, Florida, and even the Caribbean.
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.