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

Chicago → Colorado Springs via Denver: arrives on time 81%

  1. 05:15 MDW → 06:50 DEN
    WN 2989 · Southwest · 2h 35m · 98% on time, 0.0% cancelled
  2. 2h 55m layover in Denver (DEN) · 90 min minimum on separate tickets
  3. 09:45 DEN → 10:46 COS
    UA 5306 · United, flown by SkyWest · 1h 01m · 83% on time, 2.5% cancelled

Total trip 6h 31m, scheduled departure to arrival (Colorado Springs is 1 h behind Chicago). Times are local. Both flew on 43 of the last 56 days.

Makes the connection100%The first flight arrived more than 85 minutes late on 0% of the days it flew: too late for the 90-minute minimum connection on a 2h 55m layover.
Arrives on time81%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (2.5% are) and within 15 minutes (83%).
Total trip6h 31mMDW 05:15 to COS 10:46, 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.