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

New York → Chicago via St Louis: arrives on time 35%

  1. 18:30 LGA → 20:30 STL
    WN 4895 · Southwest · 3h 00m · 49% on time, 17.5% cancelled
  2. 1h 15m layover in St Louis (STL) · 45 min minimum on one ticket
  3. 21:45 STL → 22:55 MDW
    WN 3957 · Southwest · 1h 05m · 67% on time, 0.0% cancelled

Total trip 5h 20m, scheduled departure to arrival (Chicago is 1 h behind New York). Times are local. Both flew on 55 of the last 56 days.

Makes the connection64%The first flight arrived more than 30 minutes late on 36% of the days it flew: too late for the 45-minute minimum connection on a 1h 15m layover.
Arrives on time35%First flight not cancelled (17.5% are) × connection made (64%) × second flight not cancelled (0.0% are) and within 15 minutes (67%).
Total trip5h 20mLGA 18:30 to MDW 22:55, 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.