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 Chicago on time 84% of the time.

Best connections, any airlines

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


Alaska + Unitedtwo ticketsDetails →	OAK 17:35 → PDX 19:12AS 2304 · flown by Horizon	3h 28m Portland	PDX 22:40 → ORD 04:45 +1UA 2094	9h 10m	100%	90%
Southwest + Unitedtwo ticketsDetails →	OAK 18:10 → LAS 19:45WN 4693	3h 45m Las Vegas	LAS 23:30 → ORD 05:11 +1UA 2102	9h 01m	98%	90%
Southwest + Americantwo ticketsDetails →	OAK 05:00 → LAS 06:30WN 2325	3h 10m Las Vegas	LAS 09:40 → ORD 15:42AA 2020	8h 42m	98%	88%
Southwest + Unitedtwo ticketsDetails →	OAK 17:30 → SEA 19:30WN 4747	3h 41m Seattle	SEA 23:11 → ORD 05:18 +1UA 747	9h 48m	100%	85%
Southwest + Unitedtwo ticketsDetails →	OAK 17:30 → LAX 18:55WN 4229	3h 40m Los Angeles	LAX 22:35 → ORD 04:51 +1UA 353	9h 21m	96%	83%
Southwest + Unitedtwo ticketsDetails →	OAK 12:05 → SAN 13:35WN 3075	3h 06m San Diego	SAN 16:41 → ORD 22:59UA 2486	8h 54m	100%	82%
Southwest + Unitedtwo ticketsDetails →	OAK 06:20 → SAN 07:55WN 3073	2h 40m San Diego	SAN 10:35 → ORD 16:52UA 1710	8h 32m	100%	81%
Southwest + Americantwo ticketsDetails →	OAK 20:12 → LAX 21:38WN 2396	3h 02m Los Angeles	LAX 00:40 → ORD 07:06 +1AA 2919	8h 54m	92%	80%
Tight connection: often missed
Alaska Details →	OAK 14:50 → SAN 16:26AS 3311 · flown by SkyWest	57m San Diego	SAN 17:23 → ORD 23:36AS 1493	6h 46m	54%	37%
Alaska Details →	OAK 14:55 → SEA 17:00AS 1464	48m Seattle	SEA 17:48 → ORD 23:59AS 538	7h 04m	38%	30%

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.

Afternoon and evening

SAN · 57m · leaves 14:50 46%

SEA · 48m · leaves 14:55 62%

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