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

The nonstop is quickest: Southwest MDW → COS (2h 35m), on time 73% of the time. Southwest via Denver (4h 40m) is more reliable, 98%, but takes 2h 05m longer.

Nonstops (seasonal or thin)


Southwest	MDW	COS	2h 35m	74%	0.5%	189	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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


Southwest Details →	MDW 05:15 → DEN 06:50WN 2989	1h 10m Denver	DEN 08:00 → COS 08:55WN 3419	4h 40m	100%	98%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 35m Atlanta	ATL 11:30 → COS 12:35DL 2427	7h 35m	95%	76%
Southwest Details →	MDW 05:00 → DAL 07:15WN 1377	3h 50m Dallas	DAL 11:05 → COS 12:00WN 3257	8h 00m	100%	68%
Southwest Details →	MDW 09:55 → DEN 11:30WN 2654	1h 50m Denver	DEN 13:20 → COS 14:05WN 1228	5h 10m	96%	53%
Southwest Details →	MDW 10:10 → HOU 12:50WN 2783	2h 12m Houston	HOU 15:02 → COS 16:22WN 4385	7h 12m	95%	51%
Southwest Details →	MDW 11:20 → PHX 12:55WN 4189	3h 45m Phoenix	PHX 16:40 → COS 19:20WN 3064	9h 00m	98%	46%
Southwest Details →	MDW 16:15 → DEN 18:00WN 2769	2h 55m Denver	DEN 20:55 → COS 21:45WN 3811	6h 32m	91%	26%
Tight connection: often missed
Southwest Details →	MDW 05:20 → PHX 06:55WN 2858	50m Phoenix	PHX 07:45 → COS 10:30WN 4142	6h 10m	74%	58%
Southwest Details →	MDW 16:55 → LAS 18:45WN 2797	1h 05m Las Vegas	LAS 19:50 → COS 22:45WN 4487	6h 47m	56%	33%
Southwest Details →	MDW 18:00 → DEN 19:45WN 1497	1h 10m Denver	DEN 20:55 → COS 21:45WN 3811	4h 47m	72%	21%

Same layover, different day-part

How often the first flight arrives too late to connect (45 min minimum), for one-ticket layovers of 45–80 minutes.

Morning

DEN · 1h 10m · leaves 05:15 0%

Afternoon and evening

LAS · 1h 05m · leaves 16:55 44%

Delays build through the day, so an afternoon first leg eats the layover. A short connection is fine early in the morning and a gamble later on.

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.


Southwest WN 2951 MDW 10:02 → SLC Delta DL 4449 SLC 15:55 → COS Connection details →	3h 27m	8h 38m	100%	92%
Southwest WN 1497 MDW 18:00 → DEN United UA 4745 DEN 23:09 → COS Connection details →	3h 24m	6h 59m	96%	83%
Southwest WN 2989 MDW 05:15 → DEN United UA 5306 DEN 09:45 → COS Connection details →	2h 55m	6h 31m	100%	81%

Rank all connections, any airlines →

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