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, any airlines

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.


American + Southwesttwo ticketsDetails →	SFO 23:49 → CLT 08:05AA 1580	3h 30m Charlotte	CLT 11:35 → MDW 12:35 +1WN 4529	10h 46m	100%	96%
United + Southwesttwo ticketsDetails →	SFO 21:23 → CMH 05:15UA 1939	3h 45m Columbus	CMH 09:00 → MDW 09:10 +1WN 1197	9h 47m	100%	93%
United + Southwesttwo ticketsDetails →	SFO 23:59 → BNA 06:37UA 1815	2h 43m Nashville	BNA 09:20 → MDW 11:00 +1WN 1473	9h 01m	99%	87%
Delta + Southwesttwo ticketsDetails →	SFO 22:59 → ATL 06:40DL 495	3h 20m Atlanta	ATL 10:00 → MDW 11:00 +1WN 224	10h 01m	98%	86%
Alaska + Southwesttwo ticketsDetails →	SFO 18:46 → PDX 20:31AS 525	2h 59m Portland	PDX 23:30 → MDW 05:20 +1WN 3203	8h 34m	98%	86%
United + Southwesttwo ticketsDetails →	SFO 23:20 → PHL 07:50UA 2854	3h 32m Philadelphia	PHL 11:22 → MDW 12:32 +1WN 3224	11h 12m	100%	86%
Delta Details →	SFO 23:59 → ATL 07:42DL 690	3h 23m Atlanta	ATL 11:05 → MDW 12:05 +1DL 2417	10h 06m	99%	85%
United + Southwesttwo ticketsDetails →	SFO 19:45 → LAX 21:29UA 298	2h 26m Los Angeles	LAX 23:55 → MDW 05:55 +1WN 2413	8h 10m	100%	84%
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.

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