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 SEA → MDW flights land within a few points of 82% on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	SEA	MDW	3h 55m	82%	0.4%	678	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 Seattle). Layovers up to 4 hours. Pick a connection for the details.


Alaska + Southwesttwo ticketsDetails →	SEA 22:05 → CVG 05:30AS 298	2h 30m Hebron	CVG 08:00 → MDW 08:05 +1WN 3016	8h 00m	98%	96%
Alaska + Southwesttwo ticketsDetails →	SEA 17:45 → SJC 20:00AS 539	2h 55m San Jose	SJC 22:55 → MDW 05:00 +1WN 3886	9h 15m	100%	94%
Alaska + Southwesttwo ticketsDetails →	SEA 22:12 → CMH 05:40AS 280	3h 20m Columbus	CMH 09:00 → MDW 09:10 +1WN 1197	8h 58m	100%	93%
Alaska + Southwesttwo ticketsDetails →	SEA 21:33 → RDU 05:40AS 677	2h 25m Raleigh/Durham	RDU 08:05 → MDW 09:00 +1WN 3432	9h 27m	97%	92%
Alaska + Southwesttwo ticketsDetails →	SEA 16:45 → SAN 19:36AS 1348	3h 04m San Diego	SAN 22:40 → MDW 04:40 +1WN 257	9h 55m	96%	89%
Southwest Details →	SEA 18:05 → SMF 20:05WN 3566	3h 45m Sacramento	SMF 23:50 → MDW 05:45 +1WN 3802	9h 40m	97%	89%
Alaska + Southwesttwo ticketsDetails →	SEA 23:31 → ATL 07:24AS 464	2h 36m Atlanta	ATL 10:00 → MDW 11:00 +1WN 224	9h 29m	98%	87%
Delta + Southwesttwo ticketsDetails →	SEA 18:55 → PDX 20:02DL 3923 · flown by SkyWest	3h 28m Portland	PDX 23:30 → MDW 05:20 +1WN 3203	8h 25m	98%	86%
Tight connection: often missed
Southwest Details →	SEA 13:30 → AUS 19:40WN 4956	1h 20m Austin	AUS 21:00 → MDW 23:35WN 361	8h 02m	70%	45%
Southwest Details →	SEA 20:25 → OAK 22:35WN 2890	1h 20m Oakland	OAK 23:55 → MDW 06:00 +1WN 3059	7h 35m	49%	31%
Southwest Details →	SEA 15:05 → DAL 21:00WN 1404	1h 22m Dallas	DAL 22:22 → MDW 01:00 +1WN 1359	7h 32m	55%	18%

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 10m · leaves 05:15 4%

BWI · 50m · leaves 21:25 62%

Afternoon and evening

DTW · 1h 02m · leaves 09:45 10%

AUS · 1h 20m · leaves 13:30 30%

OAK · 1h 20m · leaves 20:25 51%

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