Direct flights from Boston to Chicago
All flights from BOS to MDW non-stop. There are direct flights from Boston Logan International Airport (BOS), Massachusetts, USA to Chicago Midway International (MDW), Illinois, USA with Southwest Airlines. 34 weekly departures are currently scheduled on this route. Departure times range from 05:20 to 22:50 depending on the schedule period. The flight distance is 863 miles (1389 km). Flight time ranges from 2 hours and 30 minutes to 3 hours.
Boston
, USA
Flight schedule from Boston to Chicago 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 2026-07-13
Boston to Chicago scheduled departures
Select a date to see every published non-stop departure between BOS and MDW.
BOS - MDW route facts
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Distance863 miles (1389 km)
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Flight time2 hours and 30 minutes to 3 hours
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Airline Southwest
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Airline alliancesLow-cost carrier
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CabinsEconomy
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Departure terminalsTerminal B
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AircraftBoeing 737-800 (winglets) Passenger/BBJ2, Boeing 737-700 Passenger (Scimitar Winglets) and Boeing 737MAX 8 Passenger
Route FAQ
Direct flights from Boston to IL, USA
From Boston to Chicago
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