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

Chicago → Boston via New York: arrives on time 83%

  1. 05:15 MDW → 08:15 LGA
    WN 2801 · Southwest · 2h 00m · 93% on time, 0.0% cancelled
  2. 2h 15m layover in New York (LGA) · 90 min minimum on separate tickets
  3. 10:30 LGA → 11:53 BOS
    AA 4367 · American, flown by Republic · 1h 23m · 89% on time, 5.6% cancelled

Total trip 5h 38m, scheduled departure to arrival (Boston is 1 h ahead of Chicago). Times are local. Both flew on 46 of the last 56 days.

Makes the connection98%The first flight arrived more than 45 minutes late on 2% of the days it flew: too late for the 90-minute minimum connection on a 2h 15m layover.
Arrives on time83%First flight not cancelled (0.0% are) × connection made (98%) × second flight not cancelled (5.6% are) and within 15 minutes (89%).
Total trip5h 38mMDW 05:15 to BOS 11:53, 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.