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

Oakland → New York via Chicago: arrives on time 54%

  1. 05:10 OAK → 11:15 MDW
    WN 2744 · Southwest · 4h 05m · 88% on time, 0.0% cancelled
  2. 3h 35m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 14:50 MDW → 17:55 LGA
    WN 2804 · Southwest · 2h 05m · 59% on time, 8.8% cancelled

Total trip 9h 45m, scheduled departure to arrival (New York is 3 h ahead of Oakland). Times are local. Both flew on 24 of the last 56 days.

Makes the connection100%The first flight arrived more than 170 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 3h 35m layover.
Arrives on time54%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (8.8% are) and within 15 minutes (59%).
Total trip9h 45mOAK 05:10 to LGA 17:55, 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.