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

San Jose → New York via Chicago: arrives on time 24%

  1. 10:40 SJC → 16:45 MDW
    WN 4357 · Southwest · 4h 05m · 65% on time, 0.0% cancelled
  2. 3h 00m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 19:45 MDW → 22:55 LGA
    WN 4120 · Southwest · 2h 12m · 27% on time, 8.8% cancelled

Total trip 9h 17m, scheduled departure to arrival (New York is 3 h ahead of San Jose). Times are local. Both flew on 32 of the last 56 days.

Makes the connection100%The first flight arrived more than 135 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 3h 00m layover.
Arrives on time24%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (8.8% are) and within 15 minutes (27%).
Total trip9h 17mSJC 10:40 to LGA 22:55, 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.