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

Boston → Chicago via Kansas City: arrives on time 15%

14:20 BOS → 16:40 MCI

WN 743 · Southwest · 3h 20m · 55% on time, 0.0% cancelled
50m layover in Kansas City (MCI) · 45 min minimum on one ticket
17:30 MCI → 18:55 MDW

WN 2029 · Southwest · 1h 25m · 40% on time, 3.8% cancelled

Total trip 5h 35m, scheduled departure to arrival (Chicago is 1 h behind Boston). Times are local. Both flew on 24 of the last 56 days.

Makes the connection38%The first flight arrived more than 5 minutes late on 62% of the days it flew: too late for the 45-minute minimum connection on a 50m layover.

Arrives on time15%First flight not cancelled (0.0% are) × connection made (38%) × second flight not cancelled (3.8% are) and within 15 minutes (40%).

Total trip5h 35mBOS 14:20 to MDW 18:55, layover included

Tight connection: often missed. The first flight is late enough to miss it on more than 1 day in 4.

Not yet counted: the second flight also leaving late (which helps), gate-to-gate distance at the hub, and rebooking after a missed connection.