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

Nonstops (seasonal or thin)


Southwest	PNS	MDW	2h 15m	76%	0.0%	124	Flying now

Best connections, any airlines

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.


American + Southwesttwo ticketsDetails →	PNS 05:22 → CLT 08:18AA 5548 · flown by PSA	3h 17m Charlotte	CLT 11:35 → MDW 12:35WN 4529	7h 13m	97%	90%
Delta Details →	PNS 07:00 → ATL 09:17DL 3129	1h 48m Atlanta	ATL 11:05 → MDW 12:05DL 2417	5h 05m	97%	82%
Delta + Southwesttwo ticketsDetails →	PNS 06:00 → ATL 08:15DL 3019	1h 45m Atlanta	ATL 10:00 → MDW 11:00WN 224	5h 00m	93%	80%
Southwest Details →	PNS 07:50 → BNA 09:20WN 3391	3h 35m Nashville	BNA 12:55 → MDW 14:30WN 1430	6h 40m	100%	78%
American + Southwesttwo ticketsDetails →	PNS 06:00 → DCA 09:29AA 5424 · flown by PSA	2h 31m Washington	DCA 12:00 → MDW 13:00WN 1445	7h 00m	89%	73%
Delta Details →	PNS 09:23 → ATL 11:35DL 3103	3h 40m Atlanta	ATL 15:15 → MDW 16:15DL 1728	6h 52m	99%	72%
Delta + Southwesttwo ticketsDetails →	PNS 08:00 → ATL 10:16DL 3067	2h 14m Atlanta	ATL 12:30 → MDW 13:25WN 225	5h 25m	95%	72%
Southwest Details →	PNS 07:00 → DAL 08:45WN 3393	1h 20m Dallas	DAL 10:05 → MDW 12:20WN 1357	5h 20m	92%	71%
Tight connection: often missed
Southwest Details →	PNS 14:10 → MCI 16:15WN 4795	1h 15m Kansas City	MCI 17:30 → MDW 18:55WN 2029	4h 45m	73%	28%
Southwest Details →	PNS 17:05 → DEN 19:10WN 1514	1h 40m Denver	DEN 20:50 → MDW 00:15 +1WN 1615	7h 07m	58%	20%

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

ATL · 54m · leaves 06:00 8%

Afternoon and evening

MCI · 1h 15m · leaves 14:10 27%

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