Direct flights from Chicago to Boston MDW → BOS
Southwest Airlines operates nonstop flights from Chicago (MDW) to Boston (BOS). The nonstop flight takes around ~1h 44m, covering 858 miles (1,381 km). Updated 11 June 2026.
MDW
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BOS
Round trip
1 adult
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Southwest Airlines
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Frequently asked questions
Is there a direct flight from Chicago to Boston?
Yes, Southwest Airlines operates nonstop flights from Chicago (MDW) to Boston (BOS).
Which airlines fly direct from Chicago to Boston?
Southwest Airlines operates nonstop flights from Chicago to Boston.
How long is the flight from Chicago to Boston?
The nonstop flight from Chicago to Boston takes ~1h 44m (approximately 1381 km).