Direct flights from Jacksonville to Chicago
All flights from JAX to MDW non-stop. There are direct flights from Jacksonville International (JAX), Florida, USA to Chicago Midway International (MDW), Illinois, USA with Southwest Airlines. 7 weekly departures are currently scheduled on this route. Departure times range from 07:00 to 19:55 depending on the schedule period. The flight distance is 854 miles (1374 km). Flight time ranges from 2 hours and 20 minutes to 2 hours and 35 minutes.
Jacksonville
, USA
Flight schedule from Jacksonville to Chicago with Southwest Airlines
This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.
Flight
The timetable & schedule information was updated at 2026-08-24
Jacksonville to Chicago scheduled departures
Select a date to see every published non-stop departure between JAX and MDW.
JAX - MDW route facts
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Distance854 miles (1374 km)
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Flight time2 hours and 20 minutes to 2 hours and 35 minutes
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Airline Southwest
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Airline alliancesLow-cost carrier
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CabinsEconomy
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AircraftBoeing 737MAX 8 Passenger, Boeing 737-700 Passenger (Scimitar Winglets) and Boeing 737-800 (winglets) Passenger/BBJ2
Route FAQ
Direct flights from Jacksonville to IL, USA
From Jacksonville to Chicago
ORD Chicago O Hare International
From Jacksonville to Belleville
BLV Scott Afb Midamerica
