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

No nonstop, and no clear pattern: the best connection reaches Oakland on time 87% of the time.

Best connections, any airlines

Ranked by chance you reach Oakland on time. Total trip = scheduled departure to arrival, layover included (Oakland is 2 h behind Chicago). Layovers up to 4 hours. Pick a connection for the details.


United + Alaskatwo ticketsDetails →	ORD 09:00 → PDX 11:38UA 1994	3h 30m Portland	PDX 15:08 → OAK 16:55AS 2035 · flown by Horizon	9h 55m	99%	99%
United + Deltatwo ticketsDetails →	ORD 08:55 → SLC 11:39UA 1972	3h 41m Salt Lake City	SLC 15:20 → OAK 16:23DL 3903 · flown by SkyWest	9h 28m	99%	89%
American + Southwesttwo ticketsDetails →	ORD 05:00 → PHX 06:32AA 2434	3h 08m Phoenix	PHX 09:40 → OAK 11:35WN 2680	8h 35m	97%	87%
Alaska Details →	ORD 14:12 → PDX 16:47AS 325	3h 07m Portland	PDX 19:54 → OAK 21:41AS 2036 · flown by Horizon	9h 29m	98%	87%
American + Alaskatwo ticketsDetails →	ORD 12:10 → PDX 14:40AA 2545	2h 53m Portland	PDX 17:33 → OAK 19:23AS 2082 · flown by Horizon	9h 13m	88%	86%
United + Alaskatwo ticketsDetails →	ORD 07:01 → SAN 09:29UA 2428	3h 01m San Diego	SAN 12:30 → OAK 14:10AS 3218 · flown by SkyWest	9h 09m	99%	83%
American + Southwesttwo ticketsDetails →	ORD 06:48 → SAN 09:08AA 2484	2h 37m San Diego	SAN 11:45 → OAK 13:25WN 3517	8h 37m	99%	82%
United + Southwesttwo ticketsDetails →	ORD 07:00 → PDX 09:34UA 2300	2h 51m Portland	PDX 12:25 → OAK 14:10WN 4928	9h 10m	99%	80%
Tight connection: often missed
Alaska Details →	ORD 08:02 → SEA 10:37AS 587	1h 04m Seattle	SEA 11:41 → OAK 13:59AS 1328	7h 57m	72%	52%
Alaska Details →	ORD 14:12 → PDX 16:47AS 325	46m Portland	PDX 17:33 → OAK 19:23AS 2082 · flown by Horizon	7h 11m	50%	49%

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 04m · leaves 08:02 28%

Afternoon and evening

PDX · 46m · leaves 14:12 50%

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.

The table above includes two-ticket connections (marked “two tickets”), held to the 90-minute minimum. One ticket only →

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