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

Take the nonstop: United SJC → ORD (4h 24m) reaches Chicago on time 9 times in 10; the most reliable connection, Delta via Salt Lake City (7h 13m), 70%.

Nonstops (seasonal or thin)


United	SJC	ORD	4h 24m	92%	1.7%	293	Flying now
American	SJC	ORD	–	100%few flights	0.0%	8	Not flying now

Best connections, any airlines

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 San Jose). Layovers up to 4 hours. Pick a connection for the details.


Delta + Americantwo ticketsDetails →	SJC 17:55 → SEA 20:13DL 3897 · flown by SkyWest	3h 43m Seattle	SEA 23:56 → ORD 06:02 +1AA 2881	10h 07m	100%	92%
Southwest + Unitedtwo ticketsDetails →	SJC 18:50 → LAS 20:20WN 2335	3h 10m Las Vegas	LAS 23:30 → ORD 05:11 +1UA 2102	8h 21m	97%	89%
Southwest + Americantwo ticketsDetails →	SJC 06:00 → LAS 07:35WN 2280	2h 05m Las Vegas	LAS 09:40 → ORD 15:42AA 2020	7h 42m	100%	88%
Delta + Unitedtwo ticketsDetails →	SJC 18:12 → LAX 19:37DL 1438	2h 58m Los Angeles	LAX 22:35 → ORD 04:51 +1UA 353	8h 39m	99%	87%
Alaska + Unitedtwo ticketsDetails →	SJC 18:37 → PDX 20:29AS 3030 · flown by SkyWest	3h 11m Portland	PDX 23:40 → ORD 05:45 +1UA 1490	9h 08m	98%	86%
Alaska + Unitedtwo ticketsDetails →	SJC 17:02 → SAN 18:36AS 3211 · flown by SkyWest	3h 49m San Diego	SAN 22:25 → ORD 04:36 +1UA 1457	9h 34m	100%	86%
Southwest + Unitedtwo ticketsDetails →	SJC 21:40 → BWI 05:45WN 621	2h 31m Baltimore	BWI 08:16 → ORD 09:30 +1UA 2749	9h 50m	98%	85%
Delta + Americantwo ticketsDetails →	SJC 20:19 → LAX 21:55DL 3883 · flown by SkyWest	2h 45m Los Angeles	LAX 00:40 → ORD 07:06 +1AA 2919	8h 47m	99%	85%
Tight connection: often missed
United Details →	SJC 14:32 → DEN 18:10UA 719	1h 00m Denver	DEN 19:10 → ORD 22:49UA 2258	6h 17m	63%	44%
American Details →	SJC 14:24 → DFW 20:06AA 436	54m Dallas-Fort Worth	DFW 21:00 → ORD 23:39AA 2346	7h 15m	51%	30%
Alaska Details →	SJC 08:20 → SEA 10:31AS 1426	58m Seattle	SEA 11:29 → ORD 17:38AS 346	7h 18m	39%	10%

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 · 46m · leaves 07:20 14%

SAN · 57m · leaves 10:03 22%

Afternoon and evening

IAH · 1h 20m · leaves 13:10 15%

MSP · 56m · leaves 13:10 16%

DFW · 54m · leaves 14:24 49%

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