Connection · two tickets · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026
Chicago → Washington via Orlando: arrives on time 87%
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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 00m layover in Orlando (MCO) · 90 min minimum on separate tickets
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10:40 MCO → 12:59 DCAAA 2088 · American · 2h 19m · 93% on time, 1.4% cancelled
Total trip 6h 49m, scheduled departure to arrival (Washington is 1 h ahead of Chicago). Times are local. Both flew on 40 of the last 56 days.
Makes the connection95%The first flight arrived more than 30 minutes late on 5% of the days it flew: too late for the 90-minute minimum connection on a 2h 00m layover.
Arrives on time87%First flight not cancelled (0.0% are) × connection made (95%) × second flight not cancelled (1.4% are) and within 15 minutes (93%).
Total trip6h 49mMDW 05:10 to DCA 12:59, 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.