Nonstop flights from Jacksonville to Chicago

Southwest Airlines flies this route daily.

JAXJacksonville International

850 mi · 7 flights a week

MDWChicago Midway International

JAXMDW

When they leave

Jacksonville time

7:00a5:35pFirst departure 7:00 AM, last 5:35 PM

Two in the morning, 7:00 AM to 7:30 AM, then two in the evening, 5:25 PM to 5:35 PM.

Every flight

Earliest first

7:00 AM→8:25 AMSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri
7:30 AM→8:50 AMSouthwest AirlinesBoeing 737-700Sat
5:25 PM→6:50 PMSouthwest AirlinesBoeing 737 MAX 8Tue, Wed
5:35 PM→7:00 PMSouthwest AirlinesBoeing 737Sun

Schedules last checked Sep 21, 2026. Times are local.

Flying from Jacksonville to Chicago

Southwest Airlines is the only airline flying nonstop from Jacksonville to Chicago, daily on the Boeing 737 MAX 8, Boeing 737 and Boeing 737-700.

The first arrival in Chicago is at 8:25 AM and the last at 7:00 PM. The flight covers 850 miles.

Flying back, Chicago to Jacksonville has 7 nonstop flights a week. From Jacksonville, O'Hare (ORD) is the other Chicago area airport with nonstop flights, 48 a week.

Return flights

Chicago to JacksonvilleView

Every Chicago airport

All Jacksonville to Chicago flightsView

Find the cheapest day to fly from Jacksonville to Chicago.

Schedules as of Oct 9, 2026.