Nonstop flights from Boston to Chicago

Southwest Airlines flies this route 4 to 5 times a day.

BOSBoston Logan International

857 mi · 32 flights a week

MDWChicago Midway International

BOSMDW

When they leave

Boston time

7:30a9:05pFirst departure 7:30 AM, last 9:05 PM

Four in the morning, 7:30 AM to 10:05 AM, then five in the afternoon, 12:40 PM to 3:55 PM, then four in the evening, 5:35 PM to 9:05 PM.

Every flight

Earliest first

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

Schedules last checked Sep 20, 2026. Times are local.

Flying from Boston to Chicago

Southwest Airlines is the only airline flying nonstop from Boston to Chicago, 4 to 5 times a day on the Boeing 737 MAX 8, Boeing 737-700 and Boeing 737.

There are 4 or 5 flights every day of the week. The first arrival in Chicago is at 9:05 AM and the last at 10:40 PM. The flight covers 857 miles.

Flying back, Chicago to Boston has 32 nonstop flights a week. From Boston, O'Hare (ORD) is the other Chicago area airport with nonstop flights, 180 a week.