tailodds FORECAST
Connection · one ticket · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026

Boston → Fort Myers via Chicago: arrives on time 83%

  1. 05:25 BOS → 07:00 MDW
    WN 3239 · Southwest · 2h 35m · 91% on time, 0.0% cancelled
  2. 2h 00m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 09:00 MDW → 12:45 RSW
    WN 3481 · Southwest · 2h 45m · 83% on time, 0.0% cancelled

Total trip 7h 20m, scheduled departure to arrival. Times are local. Both flew on 24 of the last 56 days.

Makes the connection100%The first flight arrived more than 75 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 2h 00m layover.
Arrives on time83%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (83%).
Total trip7h 20mBOS 05:25 to RSW 12:45, layover included

Not yet counted: the second flight also leaving late (which helps), gate-to-gate distance at the hub, and rebooking after a missed connection.