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 SFO → MDW (4h 05m), on time 73% of the time. Southwest via Denver (6h 15m) is more reliable, 84%, but takes 2h 10m longer.

Nonstops (seasonal or thin)


Southwest	SFO	MDW	4h 05m	74%	1.2%	485	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 San Francisco). Layovers up to 4 hours. Pick a connection for the details.


Delta Details →	SFO 23:59 → ATL 07:42DL 690	3h 23m Atlanta	ATL 11:05 → MDW 12:05 +1DL 2417	10h 06m	99%	85%
Southwest Details →	SFO 18:10 → SAN 19:45WN 4681	2h 55m San Diego	SAN 22:40 → MDW 04:40 +1WN 257	8h 30m	94%	84%
Southwest Details →	SFO 05:10 → DEN 08:40WN 1424	1h 20m Denver	DEN 10:00 → MDW 13:25WN 755	6h 15m	96%	84%
Delta Details →	SFO 22:59 → ATL 06:40DL 495	2h 29m Atlanta	ATL 09:09 → MDW 10:09 +1DL 1063	9h 10m	97%	82%
Southwest Details →	SFO 05:00 → LAS 06:35WN 4231	1h 45m Las Vegas	LAS 08:20 → MDW 13:55WN 2271	6h 55m	100%	75%
Delta Details →	SFO 22:55 → DTW 06:30DL 335	2h 20m Detroit	DTW 08:50 → MDW 09:14 +1DL 4684 · flown by Endeavor	8h 19m	98%	73%
Delta Details →	SFO 06:00 → ATL 13:40DL 570	1h 35m Atlanta	ATL 15:15 → MDW 16:15DL 1728	8h 15m	96%	72%
Delta Details →	SFO 11:38 → ATL 19:27DL 693	1h 48m Atlanta	ATL 21:15 → MDW 22:17DL 1076	8h 39m	95%	72%
Tight connection: often missed
Southwest Details →	SFO 10:00 → DEN 13:30WN 4284	1h 30m Denver	DEN 15:00 → MDW 18:20WN 1603	6h 20m	36%	21%
Southwest Details →	SFO 15:10 → DAL 20:45WN 1859	1h 37m Dallas	DAL 22:22 → MDW 01:00 +1WN 1359	7h 27m	62%	20%
Southwest Details →	SFO 09:45 → LAS 11:20WN 4249	1h 15m Las Vegas	LAS 12:35 → MDW 18:10WN 2273	6h 25m	30%	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 · 1h 20m · leaves 05:10 4%

MSP · 46m · leaves 00:35 22%

LAS · 1h 15m · leaves 09:45 70%

Afternoon and evening

LAS · 1h 05m · leaves 13:20 80%

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.


American AA 1580 SFO 23:49 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	3h 30m	10h 46m	100%	96%
United UA 1939 SFO 21:23 → CMH Southwest WN 1197 CMH 09:00 → MDW Connection details →	3h 45m	9h 47m	100%	93%
United UA 1815 SFO 23:59 → BNA Southwest WN 1473 BNA 09:20 → MDW Connection details →	2h 43m	9h 01m	99%	87%

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