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

Chicago → Colorado Springs via Denver: arrives on time 26%

  1. 16:15 MDW → 18:00 DEN
    WN 2769 · Southwest · 2h 45m · 62% on time, 1.7% cancelled
  2. 2h 55m layover in Denver (DEN) · 45 min minimum on one ticket
  3. 20:55 DEN → 21:45 COS
    WN 3811 · Southwest · 52m · 29% on time, 0.0% cancelled

Total trip 6h 32m, scheduled departure to arrival (Colorado Springs is 1 h behind Chicago). Times are local. Both flew on 40 of the last 56 days.

Makes the connection91%The first flight arrived more than 130 minutes late on 9% of the days it flew: too late for the 45-minute minimum connection on a 2h 55m layover.
Arrives on time26%First flight not cancelled (1.7% are) × connection made (91%) × second flight not cancelled (0.0% are) and within 15 minutes (29%).
Total trip6h 32mMDW 16:15 to COS 21:45, 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.