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

New York → Oakland via Chicago: arrives on time 36%

  1. 17:30 LGA → 19:20 MDW
    WN 4746 · Southwest · 2h 50m · 54% on time, 11.9% cancelled
  2. 2h 20m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 21:40 MDW → 00:15 OAK +1 day
    WN 4042 · Southwest · 4h 30m · 48% on time, 2.9% cancelled

Total trip 9h 40m, scheduled departure to arrival (Oakland is 3 h behind New York). Times are local. Both flew on 32 of the last 56 days.

Makes the connection86%The first flight arrived more than 95 minutes late on 14% of the days it flew: too late for the 45-minute minimum connection on a 2h 20m layover.
Arrives on time36%First flight not cancelled (11.9% are) × connection made (86%) × second flight not cancelled (2.9% are) and within 15 minutes (48%).
Total trip9h 40mLGA 17:30 to OAK 00:15, 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.