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, any airlines

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 + Alaskatwo ticketsDetails →	MDW 11:45 → ONT 13:50WN 2846	3h 42m Ontario	ONT 17:32 → PDX 19:49AS 2456 · flown by Horizon	10h 04m	98%	90%
Southwest + Deltatwo ticketsDetails →	MDW 05:10 → LAX 07:25WN 4637	2h 35m Los Angeles	LAX 10:00 → PDX 12:25DL 2766	9h 15m	100%	89%
Southwest + Alaskatwo ticketsDetails →	MDW 06:50 → DEN 08:20WN 2765	3h 42m Denver	DEN 12:02 → PDX 13:46AS 684	8h 56m	100%	88%
Southwest + Alaskatwo ticketsDetails →	MDW 06:30 → LAS 08:20WN 1182	2h 40m Las Vegas	LAS 11:00 → PDX 13:20AS 1467	8h 50m	98%	88%
Southwest + Alaskatwo ticketsDetails →	MDW 08:40 → PHX 10:20WN 3016	3h 44m Phoenix	PHX 14:04 → PDX 16:46AS 742	10h 06m	100%	87%
Southwest + Alaskatwo ticketsDetails →	MDW 05:52 → SAN 08:00WN 3103	3h 04m San Diego	SAN 11:04 → PDX 13:43AS 576	9h 51m	100%	86%
Southwest + Deltatwo ticketsDetails →	MDW 10:02 → SLC 12:28WN 2951	2h 56m Salt Lake City	SLC 15:24 → PDX 16:19DL 1244	8h 17m	98%	86%
Southwest + Deltatwo ticketsDetails →	MDW 07:40 → MSP 09:10WN 1243	1h 50m Minneapolis	MSP 11:00 → PDX 12:40DL 2167	7h 00m	96%	84%
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.

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