Itineraries flown on 20+ days in the Jun 6 – Jul 31, 2026 schedule · each leg’s record Aug 2025 – Jul 2026

No clear winner: airlines and hours on this route all land within a few points of 73% on time.

Nonstops


Southwest	PHX	MDW	3h 15m	73%	1.1%	2,639	Flying now
Frontier	PHX	MDW	3h 23m	69%	1.7%	118	Not 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 Phoenix). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	PHX 20:32 → MCI 01:35WN 3459	3h 40m Kansas City	MCI 05:15 → MDW 06:40 +1WN 4276	8h 08m	100%	93%
Southwest Details →	PHX 23:05 → MCO 06:20WN 4508	1h 40m Orlando	MCO 08:00 → MDW 09:50 +1WN 2835	8h 45m	98%	91%
Southwest Details →	PHX 18:15 → SAN 19:25WN 3324	3h 15m San Diego	SAN 22:40 → MDW 04:40 +1WN 257	8h 25m	98%	90%
Southwest Details →	PHX 21:25 → OMA 01:55WN 3311	3h 30m Omaha	OMA 05:25 → MDW 06:50 +1WN 4504	7h 25m	90%	87%
Southwest Details →	PHX 05:15 → DEN 08:00WN 3259	2h 00m Denver	DEN 10:00 → MDW 13:25WN 755	6h 10m	98%	85%
Southwest Details →	PHX 18:55 → LAX 20:20WN 2438	3h 35m Los Angeles	LAX 23:55 → MDW 05:55 +1WN 2413	9h 00m	100%	84%
Delta Details →	PHX 23:59 → ATL 06:39DL 929	2h 30m Atlanta	ATL 09:09 → MDW 10:09 +1DL 1063	8h 10m	99%	84%
Southwest Details →	PHX 20:55 → STL 01:52WN 3354	3h 48m St Louis	STL 05:40 → MDW 06:45 +1WN 1008	7h 50m	96%	81%
Tight connection: often missed
Southwest Details →	PHX 13:45 → DEN 16:35WN 3264	1h 00m Denver	DEN 17:35 → MDW 21:00WN 1604	5h 15m	61%	17%
Southwest Details →	PHX 10:25 → HOU 15:05WN 3067	53m Houston	HOU 15:58 → MDW 18:22WN 2042	5h 58m	46%	16%
Southwest Details →	PHX 15:20 → BNA 20:40WN 4600	1h 00m Nashville	BNA 21:40 → MDW 19:10WN 578	5h 50m	32%	13%

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

SJC · 1h 00m · leaves 07:45 6%

DEN · 1h 00m · leaves 06:15 8%

MCO · 1h 05m · leaves 23:05 14%

Afternoon and evening

DEN · 1h 00m · leaves 13:45 39%

HOU · 53m · leaves 10:25 54%

BNA · 1h 00m · leaves 15:20 68%

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.


Delta DL 929 PHX 23:59 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	3h 21m	9h 01m	99%	87%
Alaska AS 662 PHX 17:48 → PDX Southwest WN 3203 PDX 23:30 → MDW Connection details →	3h 00m	9h 32m	98%	86%
United UA 4722 PHX 18:54 → LAX Southwest WN 2413 LAX 23:55 → MDW Connection details →	3h 24m	9h 01m	100%	84%

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