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 94% 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 Santa Ana). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	SNA 18:25 → SJC 19:40WN 342	3h 15m San Jose	SJC 22:55 → MDW 05:00 +1WN 3886	8h 35m	100%	94%
Southwest Details →	SNA 18:45 → SMF 20:10WN 3872	3h 40m Sacramento	SMF 23:50 → MDW 05:45 +1WN 3802	9h 00m	100%	91%
Alaska + Southwesttwo ticketsDetails →	SNA 18:09 → PDX 20:31AS 589	2h 59m Portland	PDX 23:30 → MDW 05:20 +1WN 3203	9h 11m	100%	86%
Southwest Details →	SNA 19:00 → LAS 20:10WN 2477	3h 45m Las Vegas	LAS 23:55 → MDW 05:25 +1WN 2276	8h 25m	100%	84%
Southwest Details →	SNA 20:45 → PHX 22:05WN 3857	1h 50m Phoenix	PHX 23:55 → MDW 05:10 +1WN 3298	6h 25m	100%	81%
Southwest Details →	SNA 06:45 → SMF 08:25WN 2669	3h 35m Sacramento	SMF 12:00 → MDW 17:55WN 3769	9h 10m	100%	70%
Delta Details →	SNA 12:18 → ATL 19:41DL 1521	1h 34m Atlanta	ATL 21:15 → MDW 22:17DL 1076	7h 59m	91%	68%
Southwest Details →	SNA 20:30 → OAK 22:00WN 312	1h 55m Oakland	OAK 23:55 → MDW 06:00 +1WN 3059	7h 30m	100%	66%
Tight connection: often missed
Southwest Details →	SNA 10:55 → DEN 14:10WN 187	50m Denver	DEN 15:00 → MDW 18:20WN 1603	5h 25m	62%	36%
Southwest Details →	SNA 17:00 → LAS 18:10WN 2187	1h 10m Las Vegas	LAS 19:20 → MDW 01:30 +1WN 3200	5h 55m	72%	20%

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

SJC · 1h 20m · leaves 08:00 0%

Afternoon and evening

LAS · 1h 10m · leaves 17:00 28%

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