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, any airlines

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%
Southwest + Deltatwo ticketsDetails →	MDW 10:02 → SLC 12:28WN 2951	3h 27m Salt Lake City	SLC 15:55 → COS 17:40DL 4449 · flown by SkyWest	8h 38m	100%	92%
Southwest + Unitedtwo ticketsDetails →	MDW 18:00 → DEN 19:45WN 1497	3h 24m Denver	DEN 23:09 → COS 23:59UA 4745 · flown by SkyWest	6h 59m	96%	83%
Southwest + Unitedtwo ticketsDetails →	MDW 14:30 → DEN 16:10WN 2768	3h 40m Denver	DEN 19:50 → COS 20:46UA 5669 · flown by SkyWest	7h 16m	92%	77%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 35m Atlanta	ATL 11:30 → COS 12:35DL 2427	7h 35m	95%	76%
Southwest + Unitedtwo ticketsDetails →	MDW 11:10 → DEN 12:40WN 2960	2h 55m Denver	DEN 15:35 → COS 16:32UA 5546 · flown by SkyWest	6h 22m	96%	76%
Southwest + Unitedtwo ticketsDetails →	MDW 06:50 → DEN 08:20WN 2765	3h 12m Denver	DEN 11:32 → COS 12:23UA 1111	6h 33m	100%	75%
Southwest Details →	MDW 05:00 → DAL 07:15WN 1377	3h 50m Dallas	DAL 11:05 → COS 12:00WN 3257	8h 00m	100%	68%
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.

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