Direct flights from Chicago to Boston
All flights from MDW to BOS non-stop. There are direct flights from Chicago Midway International, Illinois, USA to Boston Logan International Airport (BOS), Massachusetts, USA every day of the week with Southwest Airlines. The flight distance is 863 miles and the trip usually takes about 2 hours and 20 minutes.
Chicago
, USA
Airlines with non-stop routes:
Southwest Airlines
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 2025-04-22
Chicago to Boston flight departures
Select a date to see all scheduled flight departures between MDW to BOS.
MDW - BOS information
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Distance863 miles (1389 km)
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Flight time2 hours and 20 minutes
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Airlines Southwest
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AlliancesOne WorldSky TeamStar Alliance
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ClassesEconomyBusinessFirst Class
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Southwest AircraftBoeing 737 Passenger
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Arrival TerminalTerminal B (Southwest)
