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 PIT → MDW flights land within a few points of 4 in 5 on time whatever the hour.

Nonstops


Southwest	PIT	MDW	1h 30m	81%	1.1%	1,118	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 (Chicago is 1 h behind Pittsburgh). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	PIT 06:45 → STL 07:30WN 3386	1h 25m St Louis	STL 08:55 → MDW 10:00WN 2570	4h 15m	100%	88%
Southwest Details →	PIT 06:30 → BNA 07:05WN 1935	2h 15m Nashville	BNA 09:20 → MDW 11:00WN 1473	5h 30m	98%	86%
Delta Details →	PIT 05:45 → ATL 07:25DL 1504	3h 40m Atlanta	ATL 11:05 → MDW 12:05DL 2417	7h 20m	99%	83%
Southwest Details →	PIT 06:00 → DAL 07:50WN 4465	2h 15m Dallas	DAL 10:05 → MDW 12:20WN 1357	7h 20m	100%	81%
Southwest Details →	PIT 05:10 → MCO 07:30WN 3374	1h 40m Orlando	MCO 09:10 → MDW 10:55WN 4037	6h 45m	98%	76%
Delta Details →	PIT 10:10 → ATL 12:00DL 1380	3h 15m Atlanta	ATL 15:15 → MDW 16:15DL 1728	7h 05m	99%	72%
Delta Details →	PIT 16:55 → ATL 18:48DL 1353	2h 27m Atlanta	ATL 21:15 → MDW 22:17DL 1076	6h 22m	96%	71%
Delta Details →	PIT 10:25 → DTW 11:38DL 5607 · flown by Republic	47m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	3h 21m	85%	69%

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

BWI · 50m · leaves 10:30 9%

DTW · 1h 06m · leaves 06:30 12%

Afternoon and evening

ATL · 59m · leaves 18:20 15%

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 384 PIT 06:38 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	3h 25m	6h 57m	99%	94%
Delta DL 1504 PIT 05:45 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	2h 35m	6h 15m	98%	85%
Delta DL 5753 PIT 06:05 → LGA Southwest WN 4573 LGA 10:55 → MDW Connection details →	3h 21m	7h 10m	99%	81%

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