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

Baltimore → Chicago via Boston: arrives on time 42%

  1. 13:50 BWI → 15:25 BOS
    WN 211 · Southwest · 1h 35m · 68% on time, 2.0% cancelled
  2. 1h 20m layover in Boston (BOS) · 45 min minimum on one ticket
  3. 16:45 BOS → 18:35 MDW
    WN 4106 · Southwest · 2h 50m · 54% on time, 2.4% cancelled

Total trip 5h 45m, scheduled departure to arrival (Chicago is 1 h behind Baltimore). Times are local. Both flew on 40 of the last 56 days.

Makes the connection81%The first flight arrived more than 35 minutes late on 19% of the days it flew: too late for the 45-minute minimum connection on a 1h 20m layover.
Arrives on time42%First flight not cancelled (2.0% are) × connection made (81%) × second flight not cancelled (2.4% are) and within 15 minutes (54%).
Total trip5h 45mBWI 13:50 to MDW 18:35, 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.