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 MDW → SAT flights land within a few points of 78% on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	MDW	SAT	2h 50m	78%	1.2%	661	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

Ranked by chance you reach San Antonio on time. Total trip = scheduled departure to arrival, layover included. Layovers up to 4 hours. Pick a connection for the details.


Southwest + Unitedtwo ticketsDetails →	MDW 05:15 → DEN 06:50WN 2989	2h 45m Denver	DEN 09:35 → SAT 12:43UA 2625	7h 28m	100%	92%
Southwest Details →	MDW 05:20 → PHX 06:55WN 2858	1h 00m Phoenix	PHX 07:55 → SAT 12:05WN 4081	6h 45m	88%	85%
Southwest Details →	MDW 06:30 → LAS 08:20WN 1182	2h 00m Las Vegas	LAS 10:20 → SAT 15:00WN 2333	8h 30m	98%	84%
Southwest + Deltatwo ticketsDetails →	MDW 07:15 → ATL 10:05WN 3054	2h 10m Atlanta	ATL 12:15 → SAT 13:38DL 1408	6h 26m	100%	84%
Delta Details →	MDW 09:54 → MSP 11:35DL 5469 · flown by Endeavor	2h 45m Minneapolis	MSP 14:20 → SAT 17:11DL 2580	7h 17m	98%	81%
Southwest + Deltatwo ticketsDetails →	MDW 07:55 → DTW 10:05WN 1775	3h 33m Detroit	DTW 13:38 → SAT 15:49DL 2458	7h 53m	100%	79%
Southwest + Frontiertwo ticketsDetails →	MDW 11:10 → DEN 12:40WN 2960	3h 00m Denver	DEN 15:40 → SAT 18:56F9 2356	7h 46m	96%	79%
Southwest + Unitedtwo ticketsDetails →	MDW 09:55 → DEN 11:30WN 2654	2h 14m Denver	DEN 13:44 → SAT 16:55UA 1022	7h 00m	90%	78%
Tight connection: often missed
Southwest Details →	MDW 18:35 → PHX 20:15WN 2862	50m Phoenix	PHX 21:05 → SAT 01:15 +1WN 3328	6h 42m	33%	15%
Southwest Details →	MDW 18:25 → DAL 20:40WN 2961	1h 05m Dallas	DAL 21:45 → SAT 22:52WN 2231	4h 28m	67%	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

DEN · 55m · leaves 05:15 2%

LAS · 1h 00m · leaves 07:30 12%

ATL · 47m · leaves 06:00 16%

Afternoon and evening

DAL · 1h 20m · leaves 16:20 22%

PHX · 50m · leaves 18:35 67%

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