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 MDW → PDX flights land within a few points of 64% on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	MDW	PDX	4h 20m	64%	1.0%	683	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

Ranked by chance you reach Portland on time. Total trip = scheduled departure to arrival, layover included (Portland is 2 h behind Chicago). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	MDW 10:20 → SMF 12:40WN 2094	1h 35m Sacramento	SMF 14:15 → PDX 15:45WN 422	7h 25m	88%	78%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 05m Atlanta	ATL 11:00 → PDX 13:00DL 2206	9h 00m	95%	77%
Southwest Details →	MDW 05:15 → DEN 06:50WN 2989	2h 45m Denver	DEN 09:35 → PDX 11:10WN 1667	7h 55m	100%	77%
Southwest Details →	MDW 06:30 → LAS 08:20WN 1182	1h 00m Las Vegas	LAS 09:20 → PDX 11:40WN 4132	7h 10m	91%	76%
Southwest Details →	MDW 07:10 → PHX 08:45WN 2520	2h 50m Phoenix	PHX 11:35 → PDX 14:10WN 2310	9h 00m	100%	71%
Delta Details →	MDW 11:05 → ATL 14:01DL 1063	2h 51m Atlanta	ATL 16:52 → PDX 18:56DL 503	9h 51m	98%	71%
Delta Details →	MDW 12:50 → ATL 15:49DL 2417	3h 51m Atlanta	ATL 19:40 → PDX 21:45DL 357	10h 55m	98%	69%
Delta Details →	MDW 13:49 → MSP 15:33DL 4820 · flown by Endeavor	3h 01m Minneapolis	MSP 18:34 → PDX 20:17DL 2151	8h 28m	91%	69%
Tight connection: often missed
Southwest Details →	MDW 16:55 → LAS 18:45WN 2797	1h 10m Las Vegas	LAS 19:55 → PDX 22:10WN 2307	7h 15m	60%	41%
Delta Details →	MDW 19:06 → MSP 20:51DL 4713 · flown by Endeavor	47m Minneapolis	MSP 21:38 → PDX 23:18DL 2391	6h 12m	51%	39%
Southwest Details →	MDW 18:00 → DEN 19:45WN 1497	1h 20m Denver	DEN 21:05 → PDX 22:45WN 1671	6h 47m	72%	23%

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 · 55m · leaves 05:15 2%

LAS · 1h 00m · leaves 06:30 9%

Afternoon and evening

ATL · 1h 03m · leaves 12:50 14%

LAS · 1h 10m · leaves 16:55 40%

MSP · 47m · leaves 19:06 49%

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.


Southwest WN 2846 MDW 11:45 → ONT Alaska AS 2456 ONT 17:32 → PDX Connection details →	3h 42m	10h 04m	98%	90%
Southwest WN 4637 MDW 05:10 → LAX Delta DL 2766 LAX 10:00 → PDX Connection details →	2h 35m	9h 15m	100%	89%
Southwest WN 2765 MDW 06:50 → DEN Alaska AS 684 DEN 12:02 → PDX Connection details →	3h 42m	8h 56m	100%	88%

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