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 SAN → MDW flights land within a few points of 4 in 5 on time whatever the hour.

Nonstops


Southwest	SAN	MDW	4h 00m	79%	1.0%	1,093	Flying now

Best connections, one ticket

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


Southwest Details →	SAN 18:05 → SJC 19:35WN 4185	3h 20m San Jose	SJC 22:55 → MDW 05:00 +1WN 3886	8h 55m	100%	94%
Southwest Details →	SAN 21:55 → MCO 05:55WN 4874	2h 05m Orlando	MCO 08:00 → MDW 09:50 +1WN 2835	9h 55m	100%	92%
Southwest Details →	SAN 19:50 → AUS 01:10WN 3477	3h 55m Austin	AUS 05:05 → MDW 07:35 +1WN 356	9h 45m	100%	89%
Southwest Details →	SAN 19:30 → SMF 21:10WN 3550	2h 40m Sacramento	SMF 23:50 → MDW 05:45 +1WN 3802	8h 15m	97%	88%
Delta Details →	SAN 22:30 → ATL 05:50DL 819	3h 19m Atlanta	ATL 09:09 → MDW 10:09 +1DL 1063	9h 39m	99%	83%
Southwest Details →	SAN 19:00 → LAS 20:25WN 4160	3h 30m Las Vegas	LAS 23:55 → MDW 05:25 +1WN 2276	8h 25m	98%	82%
Southwest Details →	SAN 07:05 → RNO 08:45WN 1283	1h 00m Reno	RNO 09:45 → MDW 15:30WN 3449	6h 25m	92%	81%
Delta Details →	SAN 10:43 → ATL 18:12DL 725	3h 03m Atlanta	ATL 21:15 → MDW 22:17DL 1076	9h 34m	99%	75%
Tight connection: often missed
Southwest Details →	SAN 08:10 → DAL 13:15WN 4751	50m Dallas	DAL 14:05 → MDW 16:20WN 1358	6h 10m	68%	39%
Southwest Details →	SAN 21:00 → SMF 22:45WN 3551	1h 05m Sacramento	SMF 23:50 → MDW 05:45 +1WN 3802	6h 45m	41%	37%
Southwest Details →	SAN 10:45 → DEN 14:08WN 3495	52m Denver	DEN 15:00 → MDW 18:20WN 1603	5h 35m	50%	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.

Morning

SJC · 58m · leaves 08:10 10%

DEN · 1h 05m · leaves 08:32 16%

Afternoon and evening

OAK · 1h 20m · leaves 21:00 47%

SMF · 1h 05m · leaves 21:00 59%

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.


Alaska AS 707 SAN 21:06 → MCO Southwest WN 2835 MCO 08:00 → MDW Connection details →	2h 42m	10h 44m	99%	92%
Alaska AS 3068 SAN 17:37 → SJC Southwest WN 3886 SJC 22:55 → MDW Connection details →	3h 44m	9h 23m	98%	90%
American AA 1860 SAN 21:25 → CLT Southwest WN 3048 CLT 07:35 → MDW Connection details →	2h 23m	9h 15m	96%	86%

Rank all connections, any airlines →

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