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

Nonstops (seasonal or thin)


Southwest	MDW	PWM	2h 15m	79%	0.7%	151	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

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


Southwest + Americantwo ticketsDetails →	MDW 05:15 → LGA 08:15WN 2801	2h 58m New York	LGA 11:13 → PWM 12:35AA 2931	6h 20m	100%	92%
Southwest + Americantwo ticketsDetails →	MDW 07:40 → PHL 10:42WN 4122	2h 03m Philadelphia	PHL 12:45 → PWM 14:16AA 2354	5h 36m	98%	87%
Southwest + Deltatwo ticketsDetails →	MDW 07:55 → DTW 10:05WN 1775	3h 55m Detroit	DTW 14:00 → PWM 15:55DL 1821	7h 00m	100%	87%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	1h 25m Atlanta	ATL 10:20 → PWM 13:00DL 2479	6h 00m	93%	79%
Southwest Details →	MDW 07:00 → BWI 09:45WN 2742	1h 05m Baltimore	BWI 10:50 → PWM 12:20WN 1065	4h 20m	94%	79%
Southwest + Americantwo ticketsDetails →	MDW 07:50 → CLT 10:55WN 2749	3h 58m Charlotte	CLT 14:53 → PWM 17:09AA 2352	8h 19m	100%	79%
Southwest Details →	MDW 08:55 → BWI 11:45WN 1355	3h 30m Baltimore	BWI 15:15 → PWM 16:45WN 297	6h 50m	100%	77%
Southwest + Americantwo ticketsDetails →	MDW 06:00 → DCA 08:45WN 4976	1h 48m Washington	DCA 10:33 → PWM 12:11AA 344	5h 11m	96%	73%

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