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

Boston → Milwaukee via Chicago: arrives on time 25%

  1. 17:38 BOS → 19:59 ORD
    AA 1592 · American · 3h 21m · 38% on time, 8.3% cancelled
  2. 1h 21m layover in Chicago (ORD) · 45 min minimum on one ticket
  3. 21:20 ORD → 22:23 MKE
    AA 6357 · American, flown by SkyWest · 1h 01m · 51% on time, 4.3% cancelled

Total trip 5h 43m, scheduled departure to arrival (Milwaukee is 1 h behind Boston). Times are local. Both flew on 56 of the last 56 days.

Makes the connection55%The first flight arrived more than 36 minutes late on 45% of the days it flew: too late for the 45-minute minimum connection on a 1h 21m layover.
Arrives on time25%First flight not cancelled (8.3% are) × connection made (55%) × second flight not cancelled (4.3% are) and within 15 minutes (51%).
Total trip5h 43mBOS 17:38 to MKE 22:23, layover included

Tight connection: often missed. The first flight is late enough to miss it on more than 1 day in 4.

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