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, any airlines

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.


Southwest + Alaskatwo ticketsDetails →	MDW 11:50 → GEG 13:35WN 4864	2h 46m Spokane	GEG 16:21 → SFO 18:45AS 3070 · flown by SkyWest	8h 55m	96%	83%
Southwest + Unitedtwo ticketsDetails →	MDW 10:08 → SAN 12:15WN 4648	3h 54m San Diego	SAN 16:09 → SFO 17:49UA 2117	9h 41m	100%	76%
Southwest + Alaskatwo ticketsDetails →	MDW 10:05 → PDX 12:25WN 2809	2h 24m Portland	PDX 14:49 → SFO 16:40AS 236	8h 35m	100%	73%
Southwest + Deltatwo ticketsDetails →	MDW 10:15 → MSP 11:45WN 2869	3h 22m Minneapolis	MSP 15:07 → SFO 17:14DL 756	8h 58m	98%	73%
Southwest + Deltatwo ticketsDetails →	MDW 07:15 → ATL 10:05WN 3054	2h 51m Atlanta	ATL 12:56 → SFO 14:50DL 750	9h 39m	100%	73%
Southwest + JetBluetwo ticketsDetails →	MDW 09:10 → BOS 12:28WN 1405	3h 22m Boston	BOS 15:50 → SFO 19:22B6 233	12h 14m	100%	72%
Southwest + Unitedtwo ticketsDetails →	MDW 05:52 → SAN 08:00WN 3103	3h 55m San Diego	SAN 11:55 → SFO 13:41UA 2428	9h 49m	100%	72%
Southwest + Unitedtwo ticketsDetails →	MDW 06:50 → DEN 08:20WN 2765	3h 01m Denver	DEN 11:21 → SFO 13:04UA 1561	8h 14m	100%	72%
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.

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