Itineraries flown on 20+ days in the Jun 6 – Jul 31, 2026 schedule · each leg’s record Aug 2025 – Jul 2026

No clear winner: Southwest’s COS → MDW flights land within a few points of 3 in 4 on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	COS	MDW	2h 20m	76%	1.1%	189	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

Ranked by chance you reach Chicago on time. Total trip = scheduled departure to arrival, layover included (Chicago is 1 h ahead of Colorado Springs). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	COS 05:45 → DEN 06:45WN 1220	3h 15m Denver	DEN 10:00 → MDW 13:25WN 755	6h 40m	98%	85%
Southwest Details →	COS 05:10 → DAL 08:00WN 1218	2h 05m Dallas	DAL 10:05 → MDW 12:20WN 1357	6h 10m	100%	79%
Southwest Details →	COS 20:55 → PHX 21:45WN 1231	2h 10m Phoenix	PHX 23:55 → MDW 05:10 +1WN 3298	7h 15m	89%	75%
Southwest Details →	COS 06:10 → LAS 07:05WN 3313	1h 15m Las Vegas	LAS 08:20 → MDW 13:55WN 2271	6h 45m	96%	72%
Delta Details →	COS 13:40 → ATL 18:45DL 2427	2h 30m Atlanta	ATL 21:15 → MDW 22:17DL 1076	7h 37m	96%	71%
Delta + Southwesttwo ticketsDetails →	COS 06:00 → ATL 10:54DL 1074	1h 36m Atlanta	ATL 12:30 → MDW 13:25WN 225	6h 25m	89%	67%
American + Frontiertwo ticketsDetails →	COS 08:01 → DFW 10:56AA 782	3h 34m Dallas-Fort Worth	DFW 14:30 → MDW 16:51F9 2882	7h 53m	98%	60%
Southwest Details →	COS 11:10 → DEN 12:05WN 4325	2h 55m Denver	DEN 15:00 → MDW 18:20WN 1603	6h 10m	100%	59%
Tight connection: often missed
Southwest Details →	COS 11:10 → DEN 12:05WN 4325	55m Denver	DEN 13:00 → MDW 16:20WN 1601	4h 10m	69%	41%

Mixing airlines

One ticketMiss it and the airline rebooks you; bags go through. 45 min is enough.

Separate ticketsMiss it and you buy a new ticket. Re-check bags, clear security again: we require 90 min.

The table above includes two-ticket connections (marked “two tickets”), held to the 90-minute minimum. One ticket only →

Regional partners count as the airline that sells them: SkyWest flying Delta Connection is one Delta ticket.

How these are worked out. Makes the connection: share of the last year’s flights where the first flight arrived with at least 45 minutes to spare (90 on separate tickets). Arrives on time: first flight not cancelled × connection made × second flight not cancelled and arriving within 15 minutes. Not yet counted: the second flight also leaving late (which helps), gate-to-gate distance at the hub, and rebooking after a missed connection.

About this data: US DOT on-time records, Aug 2025 – Jul 2026, all US airlines; regional flights count under the airline that sells them. Schedules (which flights and connections exist, and their times) are as of Jun 6 – Jul 31, 2026; seasonal flights outside that window aren’t ranked. Rebuilt monthly. JSON