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, one ticket

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.


Delta Details →	MDW 09:17 → DTW 11:35DL 4674 · flown by Endeavor	2h 25m Detroit	DTW 14:00 → PWM 15:55DL 1821	5h 38m	96%	84%
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 Details →	MDW 08:55 → BWI 11:45WN 1355	3h 30m Baltimore	BWI 15:15 → PWM 16:45WN 297	6h 50m	100%	77%
Southwest Details →	MDW 07:15 → BNA 08:40WN 2959	2h 35m Nashville	BNA 11:15 → PWM 14:40WN 651	6h 25m	98%	55%
Delta Details →	MDW 11:05 → ATL 14:01DL 1063	1h 16m Atlanta	ATL 15:17 → PWM 17:54DL 488	5h 48m	93%	51%
Southwest Details →	MDW 17:20 → BWI 20:15WN 4616	2h 20m Baltimore	BWI 22:35 → PWM 00:10 +1WN 4382	5h 50m	80%	43%

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 2801 MDW 05:15 → LGA American AA 2931 LGA 11:13 → PWM Connection details →	2h 58m	6h 20m	100%	92%
Southwest WN 4122 MDW 07:40 → PHL American AA 2354 PHL 12:45 → PWM Connection details →	2h 03m	5h 36m	98%	87%
Southwest WN 1775 MDW 07:55 → DTW Delta DL 1821 DTW 14:00 → PWM Connection details →	3h 55m	7h 00m	100%	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