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 → SJC (4h 35m), on time 7 times in 10. Southwest via San Diego (7h 08m) is more reliable, 93%, but takes 2h 33m longer.

Nonstops (seasonal or thin)


Southwest	MDW	SJC	4h 35m	70%	1.5%	519	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

Ranked by chance you reach San Jose on time. Total trip = scheduled departure to arrival, layover included (San Jose 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 → SJC 11:35WN 3336	8h 15m	100%	96%
Southwest Details →	MDW 05:52 → SAN 08:00WN 3103	1h 30m San Diego	SAN 09:30 → SJC 11:00WN 4509	7h 08m	100%	93%
Southwest + Alaskatwo ticketsDetails →	MDW 10:05 → PDX 12:25WN 2809	2h 05m Portland	PDX 14:30 → SJC 16:25AS 3210 · flown by SkyWest	8h 20m	96%	92%
Southwest Details →	MDW 07:30 → LAS 09:20WN 347	2h 50m Las Vegas	LAS 12:10 → SJC 13:45WN 1242	8h 15m	100%	90%
Southwest + Deltatwo ticketsDetails →	MDW 10:02 → SLC 12:28WN 2951	2h 43m Salt Lake City	SLC 15:11 → SJC 16:07DL 1260	8h 05m	98%	88%
Southwest Details →	MDW 05:10 → LAX 07:25WN 4637	1h 35m Los Angeles	LAX 09:00 → SJC 10:15WN 2431	7h 05m	100%	86%
Southwest Details →	MDW 08:40 → PHX 10:20WN 3016	3h 35m Phoenix	PHX 13:55 → SJC 15:42WN 4102	9h 03m	100%	84%
Southwest Details →	MDW 05:15 → DEN 06:50WN 2989	1h 00m Denver	DEN 07:50 → SJC 09:25WN 494	6h 10m	98%	84%
Tight connection: often missed
Southwest Details →	MDW 13:15 → LGB 15:30WN 4413	1h 00m Long Beach	LGB 16:30 → SJC 17:45WN 4307	6h 30m	69%	52%
Southwest Details →	MDW 16:55 → LAS 18:45WN 2797	1h 25m Las Vegas	LAS 20:10 → SJC 21:40WN 2352	6h 45m	74%	51%
Southwest Details →	MDW 16:15 → DEN 18:00WN 2769	55m Denver	DEN 18:55 → SJC 20:25WN 1727	6h 12m	56%	16%

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 00m · leaves 05:15 2%

BWI · 1h 05m · leaves 08:55 5%

Afternoon and evening

LGB · 1h 00m · leaves 13:15 31%

LAS · 58m · leaves 14:18 32%

DEN · 55m · leaves 16:15 44%

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