Bahamas Scheduled Flights Extended Through August 2025!
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 partner aircraft. Tradewind can secure the ideal aircraft for your journey through our network of vetted partners. Our reach includes all the latest models of light, mid, super-mid, and heavy jets.
Tradewind offers the best availability in the industry for private service flights to Chicago, Illinois.
POPULAR ROUTES TO CHICAGO (MDW/KMDW)
IN A LIGHT JET:
| 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
Tradewind can secure the ideal aircraft for your journey through our network of vetted partners. Our reach includes all the latest models of light, mid, super-mid, and heavy jets.
Tradewind is a Part 135 operator of Pilatus PC-12 aircraft. Any travel arranged by Tradewind using a different aircraft type is neither owned nor operated by Tradewind.