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

Connect in the morning. The same one-hour layover misses 1% of the time at 9 am and 14% of the time at 7 pm.

Nonstops (seasonal or thin)


Alaska	PDX	BOS	5h 30m	82%	0.8%	533	Flying now
JetBlue	PDX	BOS	5h 22m	71%	3.6%	138	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

Ranked by chance you reach Boston on time. Total trip = scheduled departure to arrival, layover included (Boston is 3 h ahead of Portland). Layovers up to 4 hours. Pick a connection for the details.


United Details →	PDX 22:40 → ORD 04:45UA 2094	2h 48m Chicago	ORD 07:33 → BOS 11:05 +1UA 1076	9h 25m	100%	94%
Southwest Details →	PDX 23:30 → MDW 05:20WN 3203	3h 50m Chicago	MDW 09:10 → BOS 12:28 +1WN 1405	9h 58m	100%	90%
American Details →	PDX 21:47 → CLT 05:44AA 1170	3h 11m Charlotte	CLT 08:55 → BOS 11:08 +1AA 1533	10h 21m	97%	90%
Delta Details →	PDX 17:24 → SLC 20:19DL 1244	3h 12m Salt Lake City	SLC 23:31 → BOS 06:05 +1DL 696	9h 41m	100%	89%
United Details →	PDX 11:16 → SFO 13:07UA 1613	3h 08m San Francisco	SFO 16:15 → BOS 01:11 +1UA 2001	10h 55m	99%	87%
American Details →	PDX 23:07 → ORD 05:07AA 2977	3h 23m Chicago	ORD 08:30 → BOS 12:07 +1AA 4106 · flown by Envoy	10h 00m	95%	86%
United Details →	PDX 18:50 → DEN 22:29UA 2334	1h 30m Denver	DEN 23:59 → BOS 05:58 +1UA 2656	8h 08m	95%	86%
Delta Details →	PDX 00:33 → MSP 05:49DL 2359	1h 06m Minneapolis	MSP 06:55 → BOS 10:45DL 2649	7h 12m	94%	86%
Tight connection: often missed
American Details →	PDX 23:07 → ORD 05:07AA 2977	53m Chicago	ORD 06:00 → BOS 09:34 +1AA 3022	7h 27m	60%	58%
Alaska Details →	PDX 13:48 → SEA 14:43AS 2205 · flown by Horizon	53m Seattle	SEA 15:36 → BOS 23:59AS 460	7h 11m	50%	40%
United Details →	PDX 07:00 → SFO 08:56UA 2818	1h 09m San Francisco	SFO 10:05 → BOS 18:59UA 2356	8h 59m	39%	24%

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

SLC · 1h 11m · leaves 05:45 1%

DEN · 1h 09m · leaves 05:00 2%

SEA · 1h 06m · leaves 06:19 4%

Afternoon and evening

ATL · 50m · leaves 14:10 20%

SEA · 51m · leaves 21:30 21%

ORD · 1h 03m · leaves 14:25 31%

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.


Alaska AS 1631 PDX 21:31 → EWR Delta DL 5764 EWR 09:30 → BOS Connection details →	3h 31m	10h 24m	100%	93%
United UA 2094 PDX 22:40 → ORD American AA 4106 ORD 08:30 → BOS Connection details →	3h 45m	10h 27m	100%	91%
Alaska AS 376 PDX 22:59 → ORD United UA 1076 ORD 07:33 → BOS Connection details →	2h 33m	9h 06m	98%	90%

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