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

The nonstop is quickest: Southwest MDW → OAK (4h 35m), on time 64% of the time. Southwest via LAX (7h 10m) is more reliable, 83%, but takes 2h 35m longer.

Nonstops (seasonal or thin)


Southwest	MDW	OAK	4h 35m	65%	1.4%	505	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

Ranked by chance you reach Oakland on time. Total trip = scheduled departure to arrival, layover included (Oakland is 2 h behind Chicago). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	MDW 05:20 → PHX 06:55WN 2858	2h 45m Phoenix	PHX 09:40 → OAK 11:35WN 2680	8h 15m	100%	92%
Southwest Details →	MDW 05:10 → LAX 07:25WN 4637	1h 35m Los Angeles	LAX 09:00 → OAK 10:20WN 3014	7h 10m	100%	83%
Southwest Details →	MDW 05:52 → SAN 08:00WN 3103	3h 45m San Diego	SAN 11:45 → OAK 13:25WN 3517	9h 33m	100%	83%
Southwest Details →	MDW 05:15 → DEN 06:50WN 2989	55m Denver	DEN 07:45 → OAK 09:25WN 1240	6h 10m	98%	81%
Southwest Details →	MDW 07:30 → LAS 09:20WN 347	1h 30m Las Vegas	LAS 10:50 → OAK 12:30WN 322	7h 00m	100%	76%
Southwest Details →	MDW 11:45 → ONT 13:50WN 2846	2h 10m Ontario	ONT 16:00 → OAK 17:15WN 3155	7h 30m	95%	75%
Southwest Details →	MDW 10:05 → BUR 12:25WN 2741	2h 40m Burbank	BUR 15:05 → OAK 16:20WN 805	8h 15m	100%	67%
Southwest Details →	MDW 06:50 → DEN 08:20WN 2765	2h 25m Denver	DEN 10:45 → OAK 12:18WN 1577	7h 27m	100%	66%
Tight connection: often missed
Southwest Details →	MDW 14:18 → LAS 16:12WN 2795	58m Las Vegas	LAS 17:10 → OAK 18:45WN 2286	6h 27m	68%	44%
Southwest Details →	MDW 16:55 → LAS 18:45WN 2797	1h 05m Las Vegas	LAS 19:50 → OAK 21:20WN 4270	6h 30m	56%	30%
Southwest Details →	MDW 16:15 → DEN 18:00WN 2769	50m Denver	DEN 18:50 → OAK 20:25WN 1843	6h 10m	53%	15%

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 · 55m · leaves 05:15 2%

Afternoon and evening

PHX · 1h 07m · leaves 18:35 41%

LAS · 1h 05m · leaves 16:55 44%

DEN · 50m · leaves 16:15 47%

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.


Southwest WN 2951 MDW 10:02 → SLC Delta DL 3903 SLC 15:20 → OAK Connection details →	2h 52m	8h 21m	98%	89%

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