Nonstop flights from Orlando to Chicago

Southwest Airlines flies this route 5 to 7 times a day.

MCOOrlando International

991 mi · 43 flights a week

MDWChicago Midway International

MCOMDW

When they leave

Orlando time

6:55a8:55pFirst departure 6:55 AM, last 8:55 PM

Five in the morning, 6:55 AM to 10:20 AM, then five in the afternoon, 1:00 PM to 4:10 PM, then four in the evening, 5:25 PM to 8:55 PM.

Every flight

Earliest first

6:55 AM→8:45 AMSouthwest AirlinesBoeing 737Mon, Tue, Wed, Thu, Fri, Sun
7:05 AM→8:55 AMSouthwest AirlinesBoeing 737-700Sat
8:15 AM→10:00 AMSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri
10:00 AM→11:45 AMSouthwest AirlinesBoeing 737-700Mon, Thu, Fri, Sun
10:20 AM→12:05 PMSouthwest AirlinesBoeing 737Tue, Wed, Sat
1:00 PM→2:45 PMSouthwest AirlinesBoeing 737 MAX 8Tue, Wed, Sun
1:50 PM→3:35 PMSouthwest AirlinesBoeing 737-700Mon, Thu, Fri
3:20 PM→5:10 PMSouthwest AirlinesBoeing 737 MAX 8Mon, Sat
3:50 PM→5:40 PMSouthwest AirlinesBoeing 737-700Tue, Wed
4:10 PM→6:00 PMSouthwest AirlinesBoeing 737-700Mon, Thu, Fri
5:25 PM→7:15 PMSouthwest AirlinesBoeing 737Tue, Wed
7:15 PM→9:00 PMSouthwest AirlinesBoeing 737Tue, Wed, Sat, Sun
7:45 PM→9:30 PMSouthwest AirlinesBoeing 737-700Fri
7:45 PM→9:30 PMSouthwest AirlinesBoeing 737-700Thu
8:55 PM→10:45 PMSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri, Sat, Sun

Schedules last checked Sep 8, 2026. Times are local.

Flying from Orlando to Chicago

Southwest Airlines is the only airline flying nonstop from Orlando to Chicago, 5 to 7 times a day on the Boeing 737-700, Boeing 737 and Boeing 737 MAX 8.

Flights run every day of the week, from 5 on Saturdays and Sundays to 7 on Mondays, Thursdays and Fridays. The first arrival in Chicago is at 8:45 AM and the last at 10:45 PM. The flight covers 991 miles.

Flying back, Chicago to Orlando has 33 nonstop flights a week. From Orlando, O'Hare (ORD) is the other Chicago area airport with nonstop flights, 113 a week.