Connection · two tickets · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026
Chicago → Portland via New York: arrives on time 92%
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05:15 MDW → 08:15 LGAWN 2801 · Southwest · 2h 00m · 93% on time, 0.0% cancelled
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2h 58m layover in New York (LGA) · 90 min minimum on separate tickets
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11:13 LGA → 12:35 PWMAA 2931 · American · 1h 22m · 92% on time, 0.0% cancelled
Total trip 6h 20m, scheduled departure to arrival (Portland is 1 h ahead of Chicago). Times are local. Both flew on 38 of the last 56 days.
Makes the connection100%The first flight arrived more than 88 minutes late on 0% of the days it flew: too late for the 90-minute minimum connection on a 2h 58m layover.
Arrives on time92%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (92%).
Total trip6h 20mMDW 05:15 to PWM 12:35, 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.