Flights from Boston (BOS) to Chicago (MDW)

Route intelligence for BOS → MDW: direct flights, stopover options, and timetable coverage in one place.

Show route on mapAll flights from BOSAll flights to MDW

Direct flights

No direct flights currently listed. See stopover options below.

Stopover options

  • No stopover itineraries available.

Timetable coverage

Published flight numbers: WN744, WN175, WN672, WN669

Flight number: WN 744

Operating days: 7

  • BOS 07:05 → MDW 08:40

Plan this city pair

Compare nearby alternatives and airline networks to decide whether a direct trip, one-stop connection, or reverse search gives you better options.

Explore all departures from BOS →Explore all arrivals to MDW →Compare airline network coverage →Browse airports by country →

Route planning checklist

  • Compare direct duration with one-stop total duration before committing to a fare.
  • Check inbound alternatives on flights to MDW when return timing is important.
  • Use Guides for alliance and hub strategy playbooks.
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