Nonstop flights from Chicago to Boston

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

MDWChicago Midway International

857 mi · 32 flights a week

BOSBoston Logan International

MDWBOS

When they leave

Chicago time

5:45a6:30pFirst departure 5:45 AM, last 6:30 PM

Seven in the morning, 5:45 AM to 11:35 AM, then four in the afternoon, 12:05 PM to 3:10 PM, then two in the evening, 5:55 PM to 6:30 PM.

Every flight

Earliest first

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

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

Flying from Chicago to Boston

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

There are 4 or 5 flights every day of the week. The first arrival in Boston is at 9:00 AM and the last at 9:50 PM. The flight covers 857 miles.

Flying back, Boston to Chicago has 32 nonstop flights a week. O'Hare (ORD) also has nonstop flights to Boston, 179 a week.

Return flights

Boston to ChicagoView

Every Chicago airport

All Chicago to Boston flightsView

Find the cheapest day to fly from Chicago to Boston.

Schedules as of Oct 9, 2026.