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

Chicago → Pittsburgh via Orlando: arrives on time 56%

  1. 08:00 MDW → 11:35 MCO
    WN 2817 · Southwest · 2h 35m · 78% on time, 2.4% cancelled
  2. 1h 05m layover in Orlando (MCO) · 45 min minimum on one ticket
  3. 12:40 MCO → 15:00 PIT
    WN 3379 · Southwest · 2h 20m · 73% on time, 2.0% cancelled

Total trip 6h 00m, scheduled departure to arrival (Pittsburgh is 1 h ahead of Chicago). Times are local. Both flew on 40 of the last 56 days.

Makes the connection80%The first flight arrived more than 20 minutes late on 20% of the days it flew: too late for the 45-minute minimum connection on a 1h 05m layover.
Arrives on time56%First flight not cancelled (2.4% are) × connection made (80%) × second flight not cancelled (2.0% are) and within 15 minutes (73%).
Total trip6h 00mMDW 08:00 to PIT 15:00, 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.