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 MSY → MDW flights land within a few points of 3 in 4 on time whatever the hour.

Nonstops


Southwest	MSY	MDW	2h 20m	76%	1.2%	1,014	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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


Southwest Details →	MSY 06:05 → AUS 07:30WN 2976	2h 55m Austin	AUS 10:25 → MDW 12:55WN 4077	6h 50m	100%	88%
Southwest Details →	MSY 05:10 → DEN 06:55WN 2991	3h 05m Denver	DEN 10:00 → MDW 13:25WN 755	8h 15m	98%	86%
Delta Details →	MSY 05:20 → ATL 07:53DL 1547	3h 12m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 45m	99%	85%
Southwest Details →	MSY 05:20 → DAL 06:45WN 2964	3h 20m Dallas	DAL 10:05 → MDW 12:20WN 1357	7h 00m	100%	81%
Southwest Details →	MSY 07:45 → BNA 09:20WN 2981	3h 35m Nashville	BNA 12:55 → MDW 14:30WN 1430	6h 45m	100%	78%
Southwest Details →	MSY 07:30 → DCA 11:00WN 222	1h 00m Washington	DCA 12:00 → MDW 13:00WN 1445	5h 30m	92%	78%
Southwest Details →	MSY 05:55 → HOU 07:10WN 4547	1h 00m Houston	HOU 08:10 → MDW 10:40WN 1294	4h 45m	89%	75%
Southwest Details →	MSY 05:00 → MCO 07:50WN 4663	1h 20m Orlando	MCO 09:10 → MDW 10:55WN 4037	5h 55m	98%	74%
Tight connection: often missed
Delta Details →	MSY 17:07 → ATL 19:45DL 924	1h 30m Atlanta	ATL 21:15 → MDW 22:17DL 1076	5h 10m	69%	52%
Frontier Details →	MSY 17:16 → ATL 20:10F9 2972	50m Atlanta	ATL 21:00 → MDW 22:03F9 2291	4h 48m	33%	21%
Southwest Details →	MSY 18:40 → HOU 19:55WN 1810	50m Houston	HOU 20:45 → MDW 23:10WN 2044	4h 30m	32%	11%

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 20m · leaves 05:00 2%

ATL · 1h 16m · leaves 05:20 5%

HOU · 1h 00m · leaves 05:55 11%

Afternoon and evening

ATL · 50m · leaves 17:16 67%

HOU · 50m · leaves 18:40 68%

LAX · 50m · leaves 15:30 83%

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.


American AA 1266 MSY 06:53 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	1h 35m	5h 42m	91%	88%
Delta DL 1547 MSY 05:20 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	2h 07m	5h 40m	95%	84%
Delta DL 1534 MSY 06:20 → ATL Southwest WN 225 ATL 12:30 → MDW Connection details →	3h 36m	7h 05m	99%	74%

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