tailodds FORECAST
Connection · two tickets · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026

Portland → Chicago via New York: arrives on time 81%

  1. 06:00 PWM → 07:30 LGA
    DL 5799 · Delta, flown by Republic · 1h 29m · 100% on time, 5.5% cancelled
  2. 3h 25m layover in New York (LGA) · 90 min minimum on separate tickets
  3. 10:55 LGA → 12:15 MDW
    WN 4573 · Southwest · 2h 20m · 85% on time, 0.0% cancelled

Total trip 7h 15m, scheduled departure to arrival (Chicago is 1 h behind Portland). Times are local. Both flew on 32 of the last 56 days.

Makes the connection100%The first flight arrived more than 115 minutes late on 0% of the days it flew: too late for the 90-minute minimum connection on a 3h 25m layover.
Arrives on time81%First flight not cancelled (5.5% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (85%).
Total trip7h 15mPWM 06:00 to MDW 12:15, 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.