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 3 in 4 on time.

Nonstops


American	ORD	PWM	2h 32m	77%	3.2%	677	Flying now
United	ORD	PWM	2h 32m	74%	2.1%	817	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.


United Details →	ORD 06:30 → IAD 09:24UA 1689	3h 21m Dulles	IAD 12:45 → PWM 14:34UA 3535 · flown by Republic	7h 04m	100%	89%
American Details →	ORD 06:00 → LGA 09:16AA 327	1h 57m New York	LGA 11:13 → PWM 12:35AA 2931	5h 35m	97%	89%
United Details →	ORD 06:00 → EWR 09:12UA 2295	2h 47m Newark	EWR 11:59 → PWM 13:25UA 3685 · flown by Republic	6h 25m	99%	88%
Delta Details →	ORD 05:30 → ATL 08:33DL 1264	1h 47m Atlanta	ATL 10:20 → PWM 13:00DL 2479	6h 30m	96%	83%
Delta Details →	ORD 08:52 → DTW 11:23DL 4456 · flown by SkyWest	2h 37m Detroit	DTW 14:00 → PWM 15:55DL 1821	6h 03m	94%	82%
American Details →	ORD 06:36 → PHL 09:46AA 2115	2h 59m Philadelphia	PHL 12:45 → PWM 14:16AA 2354	6h 40m	96%	80%
United Details →	ORD 11:07 → IAD 14:12UA 1869	3h 18m Dulles	IAD 17:30 → PWM 19:27UA 3651 · flown by Republic	7h 20m	99%	77%
American Details →	ORD 08:00 → CLT 11:08AA 3222	3h 45m Charlotte	CLT 14:53 → PWM 17:09AA 2352	8h 09m	97%	74%
Tight connection: often missed
Delta Details →	ORD 11:23 → ATL 14:25DL 1147	52m Atlanta	ATL 15:17 → PWM 17:54DL 488	5h 30m	75%	41%
Delta Details →	ORD 18:00 → JFK 21:40DL 4783 · flown by Endeavor	1h 19m New York	JFK 22:59 → PWM 00:52 +1DL 5411 · flown by Endeavor	5h 52m	69%	39%
Delta Details →	ORD 17:35 → LGA 21:00DL 2336	59m New York	LGA 21:59 → PWM 23:29DL 5705 · flown by Republic	4h 55m	50%	25%

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

DCA · 1h 18m · leaves 05:58 8%

DEN · 59m · leaves 07:05 8%

IAD · 53m · leaves 08:40 10%

Afternoon and evening

DCA · 1h 10m · leaves 17:56 38%

LGA · 59m · leaves 17:35 50%

IAD · 48m · leaves 18:12 59%

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.


American AA 4103 ORD 07:30 → DTW Delta DL 1821 DTW 14:00 → PWM Connection details →	3h 57m	7h 25m	100%	87%
United UA 2617 ORD 06:00 → LGA American AA 2931 LGA 11:13 → PWM Connection details →	2h 02m	5h 35m	96%	87%
United UA 2038 ORD 07:15 → PHL American AA 2354 PHL 12:45 → PWM Connection details →	2h 15m	6h 01m	96%	85%

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