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

Nonstops


Southwest	MDW	PIT	1h 25m	82%	1.4%	1,116	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

Ranked by chance you reach Pittsburgh on time. Total trip = scheduled departure to arrival, layover included (Pittsburgh is 1 h ahead of Chicago). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	MDW 07:15 → ATL 10:05WN 3054	3h 05m Atlanta	ATL 13:10 → PIT 14:50WN 236	6h 35m	100%	85%
Southwest Details →	MDW 05:10 → MCO 08:40WN 2815	1h 25m Orlando	MCO 10:05 → PIT 12:25WN 2684	6h 15m	98%	84%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 05m Atlanta	ATL 11:00 → PIT 12:42DL 1345	5h 42m	95%	79%
Delta Details →	MDW 11:05 → ATL 14:01DL 1063	1h 28m Atlanta	ATL 15:29 → PIT 17:15DL 1568	5h 10m	94%	76%
Southwest Details →	MDW 06:50 → DEN 08:20WN 2765	1h 45m Denver	DEN 10:05 → PIT 15:15WN 4012	7h 25m	100%	76%
Southwest Details →	MDW 07:00 → BWI 09:45WN 2742	55m Baltimore	BWI 10:40 → PIT 11:45WN 1052	3h 45m	84%	74%
Southwest Details →	MDW 07:50 → STL 09:10WN 2900	55m St Louis	STL 10:05 → PIT 12:40WN 3971	3h 50m	93%	73%
Delta Details →	MDW 17:10 → ATL 20:22DL 1728	2h 44m Atlanta	ATL 23:06 → PIT 00:52 +1DL 1351	6h 42m	95%	73%

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

STL · 55m · leaves 07:50 7%

MCO · 1h 05m · leaves 08:00 20%

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 2038 MDW 08:05 → LGA Delta DL 5715 LGA 13:10 → PIT Connection details →	1h 50m	5h 49m	100%	85%
Southwest WN 2801 MDW 05:15 → LGA Delta DL 5694 LGA 10:38 → PIT Connection details →	2h 23m	6h 05m	100%	84%
Southwest WN 4154 MDW 08:55 → ATL Delta DL 1568 ATL 15:29 → PIT Connection details →	3h 44m	7h 20m	100%	83%

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