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 → SFO (4h 40m), on time almost half the time. Delta via Atlanta (7h 45m) is more reliable, 60%, but takes 3h 05m longer.

Nonstops (seasonal or thin)


Southwest	MDW	SFO	4h 40m	49%	1.2%	485	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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


Delta Details →	MDW 09:54 → MSP 11:35DL 5469 · flown by Endeavor	3h 32m Minneapolis	MSP 15:07 → SFO 17:14DL 756	9h 19m	98%	73%
Delta Details →	MDW 12:50 → ATL 15:49DL 2417	2h 19m Atlanta	ATL 18:08 → SFO 20:05DL 517	9h 17m	97%	65%
Delta Details →	MDW 17:10 → ATL 20:22DL 1728	2h 18m Atlanta	ATL 22:40 → SFO 00:40 +1DL 656	9h 30m	93%	62%
Delta Details →	MDW 11:05 → ATL 14:01DL 1063	1h 34m Atlanta	ATL 15:35 → SFO 17:31DL 823	8h 32m	95%	60%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	50m Atlanta	ATL 09:45 → SFO 11:45DL 672	7h 45m	87%	60%
Delta Details →	MDW 13:49 → MSP 15:33DL 4820 · flown by Endeavor	3h 17m Minneapolis	MSP 18:50 → SFO 21:00DL 2809	9h 11m	94%	59%
Southwest Details →	MDW 18:35 → PHX 20:15WN 2862	2h 35m Phoenix	PHX 22:50 → SFO 00:55 +1WN 1098	8h 20m	96%	52%
Delta Details →	MDW 13:26 → DTW 15:44DL 4688 · flown by Endeavor	3h 11m Detroit	DTW 18:55 → SFO 20:59DL 509	9h 33m	94%	51%
Tight connection: often missed
Southwest Details →	MDW 10:05 → BUR 12:25WN 2741	47m Burbank	BUR 13:12 → SFO 14:35WN 2165	6h 27m	75%	39%
Delta Details →	MDW 19:06 → MSP 20:51DL 4713 · flown by Endeavor	51m Minneapolis	MSP 21:42 → SFO 23:50DL 2089	6h 43m	54%	33%
Southwest Details →	MDW 16:55 → LAS 18:45WN 2797	1h 20m Las Vegas	LAS 20:05 → SFO 21:35WN 4397	6h 40m	72%	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 · 58m · leaves 05:15 2%

ATL · 50m · leaves 06:00 13%

Afternoon and evening

LAS · 1h 20m · leaves 16:55 28%

PHX · 1h 15m · leaves 18:35 35%

MSP · 51m · leaves 19:06 46%

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 4864 MDW 11:50 → GEG Alaska AS 3070 GEG 16:21 → SFO Connection details →	2h 46m	8h 55m	96%	83%
Southwest WN 4648 MDW 10:08 → SAN United UA 2117 SAN 16:09 → SFO Connection details →	3h 54m	9h 41m	100%	76%
Southwest WN 2809 MDW 10:05 → PDX Alaska AS 236 PDX 14:49 → SFO Connection details →	2h 24m	8h 35m	100%	73%

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