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 → HOU flights land within a few points of 3 in 4 on time whatever the hour.

Nonstops


Southwest	MDW	HOU	2h 40m	75%	1.2%	1,857	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

Ranked by chance you reach Houston on time. Total trip = scheduled departure to arrival, layover included. Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	MDW 05:20 → PHX 06:55WN 2858	1h 10m Phoenix	PHX 08:05 → HOU 12:40WN 2833	7h 20m	94%	88%
Southwest Details →	MDW 08:00 → MCI 09:30WN 2808	2h 25m Kansas City	MCI 11:55 → HOU 14:05WN 2555	6h 05m	100%	84%
Southwest Details →	MDW 05:10 → MCO 08:40WN 2815	1h 00m Orlando	MCO 09:40 → HOU 11:10WN 3174	6h 00m	93%	84%
Southwest Details →	MDW 05:15 → LGA 08:15WN 2801	2h 15m New York	LGA 10:30 → HOU 13:20WN 1711	8h 05m	100%	82%
Southwest Details →	MDW 06:50 → DEN 08:20WN 2765	1h 55m Denver	DEN 10:15 → HOU 13:55WN 1543	7h 05m	100%	81%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 10m Atlanta	ATL 11:05 → HOU 12:11DL 1195	6h 12m	95%	78%
Southwest Details →	MDW 05:00 → DAL 07:15WN 1377	1h 15m Dallas	DAL 08:30 → HOU 09:45WN 7	4h 45m	96%	77%
Southwest Details →	MDW 06:40 → DAL 09:00WN 3796	1h 30m Dallas	DAL 10:30 → HOU 11:45WN 23	5h 05m	96%	73%
Tight connection: often missed
Southwest Details →	MDW 11:20 → BNA 12:45WN 2733	1h 10m Nashville	BNA 13:55 → HOU 15:55WN 533	4h 35m	69%	27%
Southwest Details →	MDW 09:45 → LGA 12:50WN 4044	50m New York	LGA 13:40 → HOU 16:30WN 4861	6h 45m	52%	26%
Southwest Details →	MDW 14:55 → FLL 18:55WN 4899	1h 15m Fort Lauderdale	FLL 20:10 → HOU 21:45WN 4583	6h 50m	65%	19%

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

BWI · 1h 15m · leaves 08:55 5%

MCO · 1h 00m · leaves 05:10 7%

Afternoon and evening

CMH · 1h 00m · leaves 16:40 36%

LAS · 1h 10m · leaves 16:55 40%

DEN · 58m · leaves 14:30 50%

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 4154 MDW 08:55 → ATL Delta DL 2381 ATL 15:11 → HOU Connection details →	3h 26m	7h 30m	100%	79%
Southwest WN 4592 MDW 14:40 → ATL Delta DL 2051 ATL 20:35 → HOU Connection details →	3h 00m	7h 03m	90%	64%
Delta DL 1063 MDW 11:05 → ATL Southwest WN 206 ATL 16:05 → HOU Connection details →	2h 04m	6h 10m	93%	59%

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