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 3% of the time at 9 am and 42% of the time at 6 pm.

Nonstops


United	PDX	ORD	4h 07m	83%	0.8%	1,402	Flying now
Alaska	PDX	ORD	4h 13m	78%	1.4%	510	Flying now
American	PDX	ORD	4h 10m	75%	1.1%	896	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 2 h ahead of Portland). Layovers up to 4 hours. Pick a connection for the details.


United Details →	PDX 23:30 → IAD 07:32UA 498	2h 59m Dulles	IAD 10:31 → ORD 11:53 +1UA 1252	10h 23m	100%	89%
United Details →	PDX 18:03 → SFO 19:53UA 1656	3h 37m San Francisco	SFO 23:30 → ORD 05:57 +1UA 368	9h 54m	100%	85%
United Details →	PDX 23:59 → IAH 06:05UA 780	3h 30m Houston	IAH 09:35 → ORD 12:29 +1UA 2124	10h 30m	99%	84%
Delta Details →	PDX 23:15 → DTW 06:30DL 919	3h 45m Detroit	DTW 10:15 → ORD 10:50 +1DL 3673 · flown by SkyWest	9h 35m	96%	83%
United Details →	PDX 05:00 → DEN 08:31UA 459	1h 04m Denver	DEN 09:35 → ORD 13:15UA 2329	6h 15m	97%	81%
United Details →	PDX 05:15 → SFO 07:01UA 1896	1h 14m San Francisco	SFO 08:15 → ORD 14:50UA 1568	7h 35m	95%	81%
United Details →	PDX 11:16 → SFO 13:07UA 1613	3h 14m San Francisco	SFO 16:21 → ORD 22:59UA 1482	9h 43m	100%	81%
Alaska Details →	PDX 21:30 → SEA 22:27AS 2421 · flown by Horizon	1h 50m Seattle	SEA 00:17 → ORD 06:20 +1AS 328	6h 50m	98%	80%
Tight connection: often missed
Delta Details →	PDX 11:55 → DTW 19:08DL 2171	52m Detroit	DTW 20:00 → ORD 20:31DL 1665	6h 36m	72%	46%
American Details →	PDX 15:31 → PHX 18:12AA 2986	57m Phoenix	PHX 19:09 → ORD 00:51 +1AA 3137	7h 20m	58%	32%
United Details →	PDX 07:00 → SFO 08:56UA 2818	1h 09m San Francisco	SFO 10:05 → ORD 16:38UA 1954	7h 38m	39%	27%

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

SEA · 1h 17m · leaves 06:19 2%

DEN · 1h 04m · leaves 05:00 3%

SFO · 1h 14m · leaves 05:15 5%

Afternoon and evening

ANC · 46m · leaves 17:50 28%

PHX · 57m · leaves 15:31 42%

DFW · 49m · leaves 11:54 44%

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 1622 PDX 17:59 → SMF American AA 3060 SMF 23:10 → ORD Connection details →	3h 33m	9h 34m	98%	91%
Alaska AS 436 PDX 21:56 → BOS American AA 1239 BOS 08:58 → ORD Connection details →	2h 38m	11h 04m	99%	90%
Alaska AS 531 PDX 17:50 → LAS United UA 2102 LAS 23:30 → ORD Connection details →	3h 18m	9h 21m	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