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 → PNS flights land within a few points of 88% on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	MDW	PNS	2h 15m	88%	0.8%	124	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

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


Southwest + Deltatwo ticketsDetails →	MDW 07:15 → ATL 10:05WN 3054	2h 45m Atlanta	ATL 12:50 → PNS 13:00DL 1640	5h 48m	100%	86%
Southwest + Deltatwo ticketsDetails →	MDW 08:55 → ATL 11:45WN 4154	3h 26m Atlanta	ATL 15:11 → PNS 15:26DL 1013	6h 31m	100%	84%
Southwest + Americantwo ticketsDetails →	MDW 08:30 → MIA 12:30WN 2464	3h 01m Miami	MIA 15:31 → PNS 16:34AA 3749 · flown by Envoy	7h 58m	100%	81%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	1h 44m Atlanta	ATL 10:39 → PNS 10:51DL 3198	4h 52m	94%	80%
Delta Details →	MDW 11:05 → ATL 14:01DL 1063	2h 49m Atlanta	ATL 16:50 → PNS 17:06DL 2211	6h 01m	98%	76%
Southwest Details →	MDW 05:00 → DAL 07:15WN 1377	2h 20m Dallas	DAL 09:35 → PNS 11:25WN 3796	6h 25m	100%	75%
Southwest + Unitedtwo ticketsDetails →	MDW 06:50 → DEN 08:20WN 2765	2h 00m Denver	DEN 10:20 → PNS 14:15UA 2185	7h 25m	94%	73%
Southwest + Frontiertwo ticketsDetails →	MDW 11:10 → DEN 12:40WN 2960	2h 06m Denver	DEN 14:46 → PNS 18:41F9 3930	7h 38m	92%	73%
Tight connection: often missed
Southwest Details →	MDW 16:20 → DAL 18:35WN 2758	1h 15m Dallas	DAL 19:50 → PNS 21:35WN 1388	5h 15m	70%	22%

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.

Afternoon and evening

ATL · 1h 17m · leaves 17:10 18%

DAL · 1h 15m · leaves 16:20 30%

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