Direct flights from Chicago to Boston
All flights from MDW to BOS non-stop. There are direct flights from Chicago Midway International (MDW), Illinois, USA to Boston Logan International Airport (BOS), Massachusetts, USA with Southwest Airlines. 32 weekly departures are currently scheduled on this route. Departure times range from 05:00 to 20:40 depending on the schedule period. The flight distance is 863 miles (1389 km). Flight time ranges from 2 hours and 5 minutes to 2 hours and 30 minutes.
Chicago
, USA
Flight schedule from Chicago to Boston with Southwest Airlines
This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.
Flight
The timetable & schedule information was updated at 2026-08-24
Chicago to Boston scheduled departures
Select a date to see every published non-stop departure between MDW and BOS.
MDW - BOS route facts
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Distance863 miles (1389 km)
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Flight time2 hours and 5 minutes to 2 hours and 30 minutes
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Airline Southwest
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Airline alliancesLow-cost carrier
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CabinsEconomy
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Arrival terminalsTerminal B
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AircraftBoeing 737MAX 8 Passenger, Boeing 737-700 Passenger (Scimitar Winglets) and Boeing 737-800 (winglets) Passenger/BBJ2
