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

No clear winner: Southwest’s SJC → MDW flights land within a few points of 85% on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	SJC	MDW	4h 05m	85%	0.2%	519	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.


Alaska + Southwesttwo ticketsDetails →	SJC 18:37 → PDX 20:29AS 3030 · flown by SkyWest	3h 01m Portland	PDX 23:30 → MDW 05:20 +1WN 3203	8h 43m	98%	86%
Delta Details →	SJC 22:00 → ATL 05:34DL 2136	3h 35m Atlanta	ATL 09:09 → MDW 10:09 +1DL 1063	10h 09m	100%	85%
Southwest Details →	SJC 17:45 → SAN 19:10WN 3526	3h 30m San Diego	SAN 22:40 → MDW 04:40 +1WN 257	8h 55m	92%	85%
Southwest Details →	SJC 18:50 → LAS 20:20WN 2335	3h 35m Las Vegas	LAS 23:55 → MDW 05:25 +1WN 2276	8h 35m	100%	84%
Southwest Details →	SJC 20:20 → LAX 21:45WN 3681	2h 10m Los Angeles	LAX 23:55 → MDW 05:55 +1WN 2413	7h 35m	96%	81%
Southwest Details →	SJC 19:00 → PHX 20:55WN 3696	3h 00m Phoenix	PHX 23:55 → MDW 05:10 +1WN 3298	8h 10m	100%	79%
Southwest Details →	SJC 20:15 → ONT 21:35WN 3692	2h 20m Ontario	ONT 23:55 → MDW 05:40 +1WN 3153	7h 25m	95%	79%
Delta Details →	SJC 06:35 → ATL 14:14DL 654	1h 01m Atlanta	ATL 15:15 → MDW 16:15DL 1728	7h 40m	94%	70%
Tight connection: often missed
Southwest Details →	SJC 14:58 → SAN 16:22WN 3701	1h 08m San Diego	SAN 17:30 → MDW 23:25WN 3448	6h 27m	64%	32%
Southwest Details →	SJC 09:20 → HOU 15:10WN 3673	48m Houston	HOU 15:58 → MDW 18:22WN 2042	7h 03m	67%	24%
Southwest Details →	SJC 17:00 → LAS 18:30WN 2266	50m Las Vegas	LAS 19:20 → MDW 01:30 +1WN 3200	5h 55m	33%	9%

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

PHX · 1h 15m · leaves 16:05 35%

SAN · 1h 08m · leaves 14:58 36%

LAS · 50m · leaves 17:00 67%

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