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

Take the nonstop: Southwest OAK → MDW (4h 05m) reaches Chicago on time 85% of the time; the most reliable connection, Southwest via Las Vegas (6h 55m), 73%.

Nonstops (seasonal or thin)


Southwest	OAK	MDW	4h 05m	85%	0.2%	505	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 Oakland). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	OAK 19:00 → ONT 20:20WN 271	3h 35m Ontario	ONT 23:55 → MDW 05:40 +1WN 3153	8h 40m	100%	83%
Southwest Details →	OAK 18:25 → SAN 20:00WN 3077	2h 40m San Diego	SAN 22:40 → MDW 04:40 +1WN 257	8h 15m	85%	78%
Southwest Details →	OAK 20:12 → LAX 21:38WN 2396	2h 17m Los Angeles	LAX 23:55 → MDW 05:55 +1WN 2413	7h 43m	92%	78%
Southwest Details →	OAK 05:00 → LAS 06:30WN 2325	1h 50m Las Vegas	LAS 08:20 → MDW 13:55WN 2271	6h 55m	98%	73%
Southwest Details →	OAK 19:50 → PHX 21:50WN 3070	2h 05m Phoenix	PHX 23:55 → MDW 05:10 +1WN 3298	7h 20m	88%	73%
Southwest Details →	OAK 20:15 → LAS 21:52WN 5051	2h 03m Las Vegas	LAS 23:55 → MDW 05:25 +1WN 2276	7h 10m	89%	72%
Southwest Details →	OAK 17:30 → SEA 19:30WN 4747	3h 35m Seattle	SEA 23:05 → MDW 05:00 +1WN 2304	9h 30m	100%	67%
Southwest Details →	OAK 10:15 → PHX 12:10WN 4766	3h 45m Phoenix	PHX 15:55 → MDW 21:15WN 4085	9h 00m	100%	62%
Tight connection: often missed
Southwest Details →	OAK 20:45 → LAS 22:20WN 4503	1h 35m Las Vegas	LAS 23:55 → MDW 05:25 +1WN 2276	6h 40m	74%	62%
Southwest Details →	OAK 20:30 → PDX 22:05WN 4368	1h 25m Portland	PDX 23:30 → MDW 05:20 +1WN 3203	6h 50m	52%	46%
Southwest Details →	OAK 16:20 → PHX 18:20WN 878	55m Phoenix	PHX 19:15 → MDW 00:35 +1WN 2521	6h 15m	54%	4%

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

DEN · 1h 15m · leaves 08:20 0%

LAX · 1h 05m · leaves 09:15 6%

LAS · 50m · leaves 09:00 26%

Afternoon and evening

PHX · 55m · leaves 16:20 46%

LAX · 55m · leaves 16:00 48%

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 2096 OAK 19:13 → PDX Southwest WN 3203 PDX 23:30 → MDW Connection details →	2h 40m	8h 07m	89%	73%
Alaska AS 2298 OAK 07:52 → PDX Southwest WN 3202 PDX 11:50 → MDW Connection details →	2h 21m	7h 53m	98%	62%
Alaska AS 491 OAK 06:22 → SEA Southwest WN 3081 SEA 11:45 → MDW Connection details →	3h 19m	9h 38m	100%	56%

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