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 MDW → STL flights land within a few points of 82% on time whatever the hour.

Nonstops


Southwest	MDW	STL	1h 15m	82%	1.3%	1,708	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

Ranked by chance you reach St Louis on time. Total trip = scheduled departure to arrival, layover included. Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	MDW 06:50 → DEN 08:20WN 2765	1h 45m Denver	DEN 10:05 → STL 13:20WN 1753	6h 30m	100%	96%
Southwest Details →	MDW 10:20 → MCI 11:45WN 2529	2h 00m Kansas City	MCI 13:45 → STL 14:50WN 2083	4h 30m	100%	88%
Southwest Details →	MDW 07:45 → PNS 10:00WN 4103	1h 55m Pensacola	PNS 11:55 → STL 13:45WN 4979	6h 00m	100%	84%
Southwest Details →	MDW 05:10 → MCO 08:40WN 2815	2h 30m Orlando	MCO 11:10 → STL 12:40WN 3316	7h 30m	100%	83%
Southwest Details →	MDW 05:00 → TPA 08:25WN 2906	1h 50m Tampa	TPA 10:15 → STL 11:40WN 4049	6h 35m	100%	81%
Delta Details →	MDW 09:54 → MSP 11:35DL 5469 · flown by Endeavor	3h 40m Minneapolis	MSP 15:15 → STL 16:46DL 3185	6h 52m	98%	77%
Southwest Details →	MDW 07:15 → ATL 10:05WN 3054	3h 05m Atlanta	ATL 13:10 → STL 13:50WN 240	6h 35m	100%	76%
Southwest Details →	MDW 05:00 → DAL 07:15WN 1377	2h 25m Dallas	DAL 09:40 → STL 11:25WN 1411	6h 25m	100%	76%
Tight connection: often missed
Delta Details →	MDW 19:06 → MSP 20:51DL 4713 · flown by Endeavor	59m Minneapolis	MSP 21:50 → STL 23:22DL 1609	4h 17m	61%	47%
Southwest Details →	MDW 18:40 → BNA 20:10WN 1073	1h 28m Nashville	BNA 21:38 → STL 22:55WN 682	4h 13m	73%	39%
Southwest Details →	MDW 16:15 → DEN 18:00WN 2769	1h 15m Denver	DEN 19:15 → STL 22:28WN 1756	6h 15m	73%	27%

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

MCO · 1h 05m · leaves 06:30 7%

DTW · 53m · leaves 09:17 17%

Afternoon and evening

MSP · 59m · leaves 19:06 39%

CLE · 50m · leaves 17:25 41%

HOU · 50m · leaves 19:15 56%

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 4154 MDW 08:55 → ATL Delta DL 2700 ATL 14:09 → STL Connection details →	2h 24m	5h 55m	98%	87%
Southwest WN 2989 MDW 05:15 → DEN United UA 652 DEN 09:35 → STL Connection details →	2h 45m	7h 27m	100%	84%
Southwest WN 3054 MDW 07:15 → ATL Delta DL 566 ATL 11:52 → STL Connection details →	1h 47m	5h 15m	95%	77%

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