Itineraries flown on 20+ days in the Jun 6 – Jul 31, 2026 schedule · each leg’s record Aug 2025 – Jul 2026

No clear winner: airlines and hours on this route all land within a few points of 78% on time.

Nonstops


Southwest	MDW	PHL	1h 55m	77%	1.7%	1,454	Flying now
Frontier	MDW	PHL	2h 01m	84%	1.5%	68	Not flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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


Southwest Details →	MDW 07:50 → STL 09:10WN 2900	50m St Louis	STL 10:00 → PHL 13:10WN 3222	4h 20m	89%	79%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 26m Atlanta	ATL 11:21 → PHL 13:24DL 2279	6h 26m	95%	78%
Southwest Details →	MDW 06:50 → DEN 08:20WN 2765	2h 02m Denver	DEN 10:22 → PHL 16:00WN 3157	8h 10m	100%	72%
Delta Details →	MDW 09:54 → MSP 11:35DL 5469 · flown by Endeavor	2h 50m Minneapolis	MSP 14:25 → PHL 18:07DL 2594	7h 13m	98%	72%
Delta Details →	MDW 17:10 → ATL 20:22DL 1728	2h 33m Atlanta	ATL 22:55 → PHL 00:59 +1DL 2642	6h 50m	95%	70%
Delta Details →	MDW 09:17 → DTW 11:35DL 4674 · flown by Endeavor	3h 18m Detroit	DTW 14:53 → PHL 16:36DL 1391	6h 19m	98%	68%
Southwest Details →	MDW 07:15 → BNA 08:40WN 2959	1h 35m Nashville	BNA 10:15 → PHL 13:20WN 623	5h 05m	90%	64%
Delta Details →	MDW 13:26 → DTW 15:44DL 4688 · flown by Endeavor	1h 56m Detroit	DTW 17:40 → PHL 19:25DL 1686	4h 59m	89%	62%
Tight connection: often missed
Frontier Details →	MDW 06:00 → ATL 09:19F9 2292	51m Atlanta	ATL 10:10 → PHL 12:22F9 2298	5h 23m	58%	38%
Southwest Details →	MDW 16:15 → DEN 18:00WN 2769	1h 05m Denver	DEN 19:05 → PHL 00:45 +1WN 2686	7h 25m	64%	14%
Southwest Details →	MDW 18:40 → BNA 20:10WN 1073	1h 00m Nashville	BNA 21:10 → PHL 00:25 +1WN 634	4h 30m	50%	13%

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 · 50m · leaves 07:50 11%

ATL · 51m · leaves 06:00 42%

Afternoon and evening

DEN · 1h 05m · leaves 16:15 36%

BNA · 1h 00m · leaves 18:40 50%

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.


Frontier F9 2292 MDW 06:00 → ATL American AA 4338 ATL 12:25 → PHL Connection details →	3h 06m	7h 36m	98%	89%
Southwest WN 2906 MDW 05:00 → TPA American AA 2807 TPA 10:48 → PHL Connection details →	2h 23m	7h 27m	100%	89%
Southwest WN 2900 MDW 07:50 → STL American AA 2720 STL 11:16 → PHL Connection details →	2h 06m	5h 45m	96%	87%

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