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 PDX → MDW flights land within a few points of 9 in 10 on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	PDX	MDW	3h 55m	90%	0.7%	684	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 Portland). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	PDX 17:20 → SJC 19:05WN 3210	3h 50m San Jose	SJC 22:55 → MDW 05:00 +1WN 3886	9h 40m	100%	94%
Southwest Details →	PDX 18:00 → LAS 20:15WN 2256	3h 40m Las Vegas	LAS 23:55 → MDW 05:25 +1WN 2276	9h 25m	100%	84%
Delta Details →	PDX 22:55 → ATL 06:27DL 564	2h 42m Atlanta	ATL 09:09 → MDW 10:09 +1DL 1063	9h 14m	96%	80%
Delta Details →	PDX 00:33 → MSP 05:49DL 2359	1h 06m Minneapolis	MSP 06:55 → MDW 08:37DL 4712 · flown by Endeavor	6h 04m	94%	79%
Southwest Details →	PDX 20:15 → SMF 21:48WN 3213	2h 02m Sacramento	SMF 23:50 → MDW 05:45 +1WN 3802	7h 30m	86%	79%
Delta Details →	PDX 11:40 → ATL 19:26DL 539	1h 49m Atlanta	ATL 21:15 → MDW 22:17DL 1076	8h 37m	97%	72%
Southwest Details →	PDX 05:00 → LAS 07:10WN 344	1h 10m Las Vegas	LAS 08:20 → MDW 13:55WN 2271	6h 55m	96%	72%
Delta Details →	PDX 06:35 → ATL 14:20DL 662	55m Atlanta	ATL 15:15 → MDW 16:15DL 1728	7h 40m	93%	69%
Tight connection: often missed
Southwest Details →	PDX 21:20 → BWI 05:15WN 3194	55m Baltimore	BWI 06:10 → MDW 07:10 +1WN 995	7h 50m	72%	65%
Southwest Details →	PDX 15:15 → DAL 20:55WN 1577	1h 27m Dallas	DAL 22:22 → MDW 01:00 +1WN 1359	7h 22m	62%	20%

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

MSP · 1h 06m · leaves 00:33 6%

BWI · 55m · leaves 21:20 28%

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.


Alaska AS 2113 PDX 17:40 → SJC Southwest WN 3886 SJC 22:55 → MDW Connection details →	3h 23m	9h 20m	99%	93%
Delta DL 564 PDX 22:55 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	3h 33m	10h 05m	96%	84%
Alaska AS 278 PDX 17:37 → LAX Southwest WN 2413 LAX 23:55 → MDW Connection details →	3h 46m	10h 18m	99%	83%

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