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

Boston → Milwaukee via Chicago: arrives on time 90%

  1. 05:25 BOS → 07:00 MDW
    WN 3239 · Southwest · 2h 35m · 91% on time, 0.0% cancelled
  2. 3h 15m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 10:15 MDW → 11:00 MKE
    WN 1702 · Southwest · 45m · 90% on time, 0.0% cancelled

Total trip 6h 35m, scheduled departure to arrival (Milwaukee is 1 h behind Boston). Times are local. Both flew on 24 of the last 56 days.

Makes the connection100%The first flight arrived more than 150 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 3h 15m layover.
Arrives on time90%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (90%).
Total trip6h 35mBOS 05:25 to MKE 11:00, 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.