Nonstop flights from Chicago to Orlando

Southwest Airlines flies this route 33 times a week.

MDWChicago Midway International

991 mi · 33 flights a week

MCOOrlando International

MDWMCO

When they leave

Chicago time

5:00a8:05pFirst departure 5:00 AM, last 8:05 PM

Eight in the morning, 5:00 AM to 11:15 AM, then two in the afternoon, 12:20 PM to 3:40 PM, then four in the evening, 6:00 PM to 8:05 PM.

Every flight

Earliest first

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

Schedules last checked Sep 19, 2026. Times are local.

Flying from Chicago to Orlando

Southwest Airlines is the only airline flying nonstop from Chicago to Orlando, 33 times a week on the Boeing 737 MAX 8, Boeing 737 and Boeing 737-700.

Flights run every day except Thursdays, up to 6 a day. The first arrival in Orlando is at 8:30 AM and the last at 11:35 PM. The flight covers 991 miles.

Flying back, Orlando to Chicago has 43 nonstop flights a week. O'Hare (ORD) also has nonstop flights to Orlando, 110 a week.