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 3 in 4 on time.

Nonstops


Southwest	MDW	PHX	3h 50m	76%	1.6%	2,620	Flying now
Frontier	MDW	PHX	4h 09m	79%	1.7%	118	Not flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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


Southwest Details →	MDW 05:15 → DEN 06:50WN 2989	1h 50m Denver	DEN 08:40 → PHX 09:35WN 431	6h 20m	100%	89%
Southwest Details →	MDW 08:00 → MCI 09:30WN 2808	1h 10m Kansas City	MCI 10:40 → PHX 11:25WN 4651	5h 25m	100%	86%
Southwest Details →	MDW 07:30 → LAS 09:20WN 347	3h 10m Las Vegas	LAS 12:30 → PHX 13:50WN 2311	8h 20m	100%	86%
Southwest Details →	MDW 06:40 → HOU 09:15WN 4497	2h 45m Houston	HOU 12:00 → PHX 12:40WN 2063	8h 00m	100%	85%
Southwest Details →	MDW 06:30 → LAS 08:20WN 1182	1h 20m Las Vegas	LAS 09:40 → PHX 11:00WN 2310	6h 30m	98%	83%
Southwest Details →	MDW 05:00 → TPA 08:25WN 2906	3h 15m Tampa	TPA 11:40 → PHX 13:00WN 4040	10h 00m	100%	81%
Southwest Details →	MDW 05:52 → SAN 08:00WN 3103	1h 15m San Diego	SAN 09:15 → PHX 10:40WN 681	6h 48m	100%	81%
Southwest Details →	MDW 05:20 → AUS 07:50WN 2726	3h 55m Austin	AUS 11:45 → PHX 12:05WN 375	8h 45m	100%	80%
Tight connection: often missed
Southwest Details →	MDW 12:00 → BWI 14:50WN 2744	55m Baltimore	BWI 15:45 → PHX 17:35WN 1050	7h 35m	60%	35%
Southwest Details →	MDW 16:55 → LAS 18:45WN 2797	1h 00m Las Vegas	LAS 19:45 → PHX 21:00WN 2314	6h 05m	54%	27%
Southwest Details →	MDW 16:15 → DEN 18:00WN 2769	55m Denver	DEN 18:55 → PHX 19:50WN 1683	5h 40m	56%	16%

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 0%

SAN · 1h 15m · leaves 05:52 0%

LAS · 1h 20m · leaves 06:30 2%

Afternoon and evening

MCI · 1h 00m · leaves 16:05 24%

DEN · 55m · leaves 16:15 44%

LAS · 1h 00m · leaves 16:55 46%

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 2433 MDW 10:10 → LAX United UA 5457 LAX 16:22 → PHX Connection details →	3h 52m	9h 49m	100%	99%
Southwest WN 4637 MDW 05:10 → LAX American AA 1668 LAX 10:00 → PHX Connection details →	2h 35m	8h 18m	100%	91%
Southwest WN 2765 MDW 06:50 → DEN United UA 1686 DEN 11:25 → PHX Connection details →	3h 05m	7h 35m	100%	87%

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