Connection · two tickets · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026
Chicago → New York via Orlando: arrives on time 79%
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05:10 MDW → 08:40 MCOWN 2815 · Southwest · 2h 30m · 93% on time, 0.0% cancelled
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2h 25m layover in Orlando (MCO) · 90 min minimum on separate tickets
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11:05 MCO → 13:47 JFKDL 2049 · Delta · 2h 42m · 82% on time, 4.0% cancelled
Total trip 7h 37m, 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 55 minutes late on 0% of the days it flew: too late for the 90-minute minimum connection on a 2h 25m layover.
Arrives on time79%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (4.0% are) and within 15 minutes (82%).
Total trip7h 37mMDW 05:10 to JFK 13:47, 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.