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 PWM → MDW flights land within a few points of 9 in 10 on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	PWM	MDW	2h 35m	89%	0.0%	151	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 (Chicago is 1 h behind Portland). Layovers up to 4 hours. Pick a connection for the details.


American + Southwesttwo ticketsDetails →	PWM 07:16 → CLT 09:46AA 2966	1h 49m Charlotte	CLT 11:35 → MDW 12:35WN 4529	6h 19m	92%	88%
Delta Details →	PWM 06:00 → ATL 08:45DL 1515	2h 20m Atlanta	ATL 11:05 → MDW 12:05DL 2417	7h 05m	99%	84%
Delta + Southwesttwo ticketsDetails →	PWM 06:00 → LGA 07:30DL 5799 · flown by Republic	3h 25m New York	LGA 10:55 → MDW 12:15WN 4573	7h 15m	100%	81%
American + Southwesttwo ticketsDetails →	PWM 05:45 → DCA 07:45AA 4351 · flown by Republic	1h 40m Washington	DCA 09:25 → MDW 10:20WN 1444	5h 35m	96%	76%
American + Southwesttwo ticketsDetails →	PWM 08:00 → PHL 09:39AA 2951	1h 43m Philadelphia	PHL 11:22 → MDW 12:32WN 3224	5h 32m	88%	74%
Southwest Details →	PWM 05:35 → BWI 07:15WN 4674	2h 20m Baltimore	BWI 09:35 → MDW 10:35WN 4217	6h 00m	98%	66%
Southwest Details →	PWM 15:10 → BWI 16:55WN 183	2h 05m Baltimore	BWI 19:00 → MDW 20:05WN 1005	5h 55m	97%	62%
Delta Details →	PWM 11:48 → MSP 13:50DL 1766	2h 48m Minneapolis	MSP 16:38 → MDW 18:18DL 4714 · flown by Endeavor	7h 29m	99%	59%

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