Nonstop flights from Washington to Chicago

Southwest Airlines flies this route 5 to 6 times a day.

DCARonald Reagan Washington National

598 mi · 41 flights a week

MDWChicago Midway International

DCAMDW

When they leave

Washington time

7:25a9:15pFirst departure 7:25 AM, last 9:15 PM

Three in the morning, 7:25 AM to 9:30 AM, then three in the afternoon, 1:00 PM to 4:35 PM, then three in the evening, 6:40 PM to 9:15 PM.

Every flight

Earliest first

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

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

Flying from Washington to Chicago

Southwest Airlines is the only airline flying nonstop from Washington to Chicago, 5 to 6 times a day on the Boeing 737-700, Boeing 737 MAX 8 and Boeing 737.

There are 5 or 6 flights every day of the week. The first arrival in Chicago is at 8:20 AM and the last at 10:10 PM. The flight covers 598 miles.

Flying back, Chicago to Washington has 41 nonstop flights a week. Baltimore (BWI) also has nonstop flights to Chicago, 38 a week. From Washington, O'Hare (ORD) is the other Chicago area airport with nonstop flights, 148 a week.