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

No clear winner: airlines and hours on this route all land within a few points of 4 in 5 on time.

Nonstops


American	PWM	ORD	3h 06m	80%	4.0%	677	Flying now
United	PWM	ORD	3h 05m	78%	3.1%	817	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 1 h behind Portland). Layovers up to 4 hours. Pick a connection for the details.


United Details →	PWM 05:15 → IAD 07:00UA 1926	3h 31m Dulles	IAD 10:31 → ORD 11:53UA 1252	7h 38m	100%	91%
American Details →	PWM 07:16 → CLT 09:46AA 2966	1h 15m Charlotte	CLT 11:01 → ORD 12:19AA 2908	6h 03m	93%	83%
United Details →	PWM 06:00 → EWR 07:33UA 3604 · flown by Republic	2h 51m Newark	EWR 10:24 → ORD 12:06UA 1525	7h 06m	100%	74%
Delta Details →	PWM 06:20 → JFK 07:44DL 5277 · flown by Endeavor	2h 46m New York	JFK 10:30 → ORD 12:20DL 5119 · flown by Endeavor	7h 00m	98%	73%
American Details →	PWM 08:00 → PHL 09:39AA 2951	3h 03m Philadelphia	PHL 12:42 → ORD 14:15AA 2925	7h 15m	99%	73%
American Details →	PWM 05:45 → DCA 07:45AA 4351 · flown by Republic	3h 50m Washington	DCA 11:35 → ORD 12:53AA 489	8h 08m	98%	73%
Delta Details →	PWM 06:00 → LGA 07:30DL 5799 · flown by Republic	1h 15m New York	LGA 08:45 → ORD 10:31DL 2985	5h 31m	100%	73%
United Details →	PWM 09:55 → IAD 11:46UA 3465 · flown by Republic	1h 29m Dulles	IAD 13:15 → ORD 14:29UA 2331	5h 34m	90%	69%
Tight connection: often missed
United Details →	PWM 15:37 → DEN 18:16UA 287	54m Denver	DEN 19:10 → ORD 22:49UA 2258	8h 12m	69%	48%
Delta Details →	PWM 18:59 → ATL 21:56DL 488	54m Atlanta	ATL 22:50 → ORD 23:53DL 1199	6h 00m	64%	43%
American Details →	PWM 14:56 → PHL 16:53AA 2354	47m Philadelphia	PHL 17:40 → ORD 19:26AA 1012	5h 30m	44%	23%

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

LGA · 1h 15m · leaves 06:00 0%

IAD · 1h 15m · leaves 05:15 3%

CLT · 1h 15m · leaves 07:16 7%

Afternoon and evening

ATL · 54m · leaves 18:59 36%

DCA · 56m · leaves 17:17 41%

PHL · 47m · leaves 14:56 56%

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.


Southwest WN 4674 PWM 05:35 → BWI United UA 704 BWI 10:32 → ORD Connection details →	3h 17m	7h 13m	98%	89%
American AA 4351 PWM 05:45 → DCA United UA 2201 DCA 10:30 → ORD Connection details →	2h 45m	7h 03m	98%	81%
Delta DL 1515 PWM 06:00 → ATL United UA 1239 ATL 11:29 → ORD Connection details →	2h 44m	7h 52m	99%	80%

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