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 3 in 4 on time.

Nonstops


Southwest	PHL	MDW	2h 10m	75%	1.7%	1,455	Flying now
Frontier	PHL	MDW	2h 13m	84%	1.4%	69	Not 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 Philadelphia). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	PHL 06:12 → STL 07:32WN 3227	1h 23m St Louis	STL 08:55 → MDW 10:00WN 2570	4h 48m	96%	85%
Delta Details →	PHL 06:25 → ATL 08:32DL 1152	2h 33m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 40m	98%	83%
Delta Details →	PHL 05:15 → ATL 07:22DL 1269	1h 47m Atlanta	ATL 09:09 → MDW 10:09DL 1063	5h 54m	97%	80%
Delta Details →	PHL 10:40 → ATL 12:54DL 1100	2h 21m Atlanta	ATL 15:15 → MDW 16:15DL 1728	6h 35m	99%	72%
Delta Details →	PHL 16:08 → ATL 18:25DL 2131	2h 50m Atlanta	ATL 21:15 → MDW 22:17DL 1076	7h 09m	95%	70%
Delta Details →	PHL 09:46 → DTW 11:31DL 2968	54m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	4h 00m	86%	67%
Delta Details →	PHL 06:10 → DTW 07:50DL 1540	1h 00m Detroit	DTW 08:50 → MDW 09:14DL 4684 · flown by Endeavor	4h 04m	91%	66%
Delta Details →	PHL 12:36 → DTW 14:20DL 2331	3h 47m Detroit	DTW 18:07 → MDW 18:25DL 4677 · flown by Endeavor	6h 53m	100%	57%
Tight connection: often missed
Southwest Details →	PHL 18:00 → STL 19:30WN 2679	2h 15m St Louis	STL 21:45 → MDW 22:55WN 3957	5h 50m	72%	46%
Frontier Details →	PHL 06:30 → ATL 09:05F9 2551	1h 00m Atlanta	ATL 10:05 → MDW 11:07F9 2779	5h 39m	71%	42%
Southwest Details →	PHL 18:30 → DAL 21:00WN 3218	1h 22m Dallas	DAL 22:22 → MDW 01:00 +1WN 1359	7h 07m	48%	15%

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

DTW · 1h 00m · leaves 06:10 9%

ATL · 53m · leaves 08:05 16%

Afternoon and evening

BNA · 1h 13m · leaves 13:55 24%

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 3139 PHL 06:00 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	3h 42m	7h 35m	99%	93%
Delta DL 1269 PHL 05:15 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	2h 38m	6h 45m	97%	84%
American AA 5997 PHL 09:00 → BDL Southwest WN 427 BDL 12:40 → MDW Connection details →	2h 18m	6h 05m	99%	78%

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