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

Chicago → New York via Orlando: arrives on time 73%

  1. 08:00 MDW → 11:35 MCO
    WN 2817 · Southwest · 2h 35m · 78% on time, 2.4% cancelled
  2. 3h 22m layover in Orlando (MCO) · 90 min minimum on separate tickets
  3. 14:57 MCO → 17:44 JFK
    B6 1084 · JetBlue · 2h 54m · 79% on time, 5.6% cancelled

Total trip 8h 51m, scheduled departure to arrival (New York is 1 h ahead of Chicago). Times are local. Both flew on 40 of the last 56 days.

Makes the connection100%The first flight arrived more than 112 minutes late on 0% of the days it flew: too late for the 90-minute minimum connection on a 3h 22m layover.
Arrives on time73%First flight not cancelled (2.4% are) × connection made (100%) × second flight not cancelled (5.6% are) and within 15 minutes (79%).
Total trip8h 51mMDW 08:00 to JFK 17:44, 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.