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

Nonstops


Southwest	LAX	MDW	3h 55m	79%	0.6%	1,298	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 Los Angeles). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	LAX 22:05 → MCO 06:00WN 2409	2h 00m Orlando	MCO 08:00 → MDW 09:50 +1WN 2835	9h 45m	100%	94%
Southwest Details →	LAX 20:25 → MCI 01:35WN 2408	3h 40m Kansas City	MCI 05:15 → MDW 06:40 +1WN 4276	8h 15m	100%	93%
Delta Details →	LAX 23:58 → ATL 07:25DL 320	3h 40m Atlanta	ATL 11:05 → MDW 12:05 +1DL 2417	10h 07m	100%	85%
Delta Details →	LAX 22:45 → ATL 06:07DL 899	3h 02m Atlanta	ATL 09:09 → MDW 10:09 +1DL 1063	9h 24m	98%	83%
Southwest Details →	LAX 23:40 → HOU 05:00WN 2402	3h 10m Houston	HOU 08:10 → MDW 10:40 +1WN 1294	9h 00m	98%	83%
Southwest Details →	LAX 05:05 → BNA 11:10WN 4492	1h 45m Nashville	BNA 12:55 → MDW 14:30WN 1430	7h 25m	100%	78%
Southwest Details →	LAX 19:55 → SJC 21:15WN 2435	1h 40m San Jose	SJC 22:55 → MDW 05:00 +1WN 3886	7h 05m	80%	76%
Southwest Details →	LAX 05:35 → LAS 06:50WN 2403	1h 30m Las Vegas	LAS 08:20 → MDW 13:55WN 2271	6h 20m	100%	75%
Tight connection: often missed
Southwest Details →	LAX 21:05 → OAK 22:25WN 4554	1h 30m Oakland	OAK 23:55 → MDW 06:00 +1WN 3059	6h 55m	73%	48%
Southwest Details →	LAX 14:10 → HOU 19:35WN 3225	1h 10m Houston	HOU 20:45 → MDW 23:10WN 2044	7h 00m	37%	14%
Southwest Details →	LAX 17:00 → LAS 18:15WN 1571	1h 05m Las Vegas	LAS 19:20 → MDW 01:30 +1WN 3200	5h 55m	43%	12%

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

SMF · 1h 05m · leaves 09:30 7%

Afternoon and evening

LAS · 1h 05m · leaves 17:00 57%

HOU · 1h 10m · leaves 14:10 63%

DEN · 55m · leaves 14:45 65%

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.


Delta DL 3883 LAX 18:16 → SJC Southwest WN 3886 SJC 22:55 → MDW Connection details →	3h 23m	8h 44m	99%	93%
Delta DL 3759 LAX 18:51 → SMF Southwest WN 3802 SMF 23:50 → MDW Connection details →	3h 25m	8h 54m	99%	91%
Delta DL 4087 LAX 18:15 → SAN Southwest WN 257 SAN 22:40 → MDW Connection details →	3h 24m	8h 25m	99%	91%

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