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

Connect in the morning. The same one-hour layover misses 14% of the time at 9 am and 31% of the time at 8 pm.

Nonstops


Southwest	HOU	MDW	2h 25m	73%	1.1%	1,840	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. Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	HOU 07:50 → OMA 10:00WN 2060	3h 10m Omaha	OMA 13:10 → MDW 14:35WN 4470	6h 45m	100%	92%
Southwest Details →	HOU 05:30 → DEN 06:55WN 1970	3h 05m Denver	DEN 10:00 → MDW 13:25WN 755	7h 55m	100%	87%
Southwest Details →	HOU 05:50 → ATL 08:50WN 2622	1h 10m Atlanta	ATL 10:00 → MDW 11:00WN 224	5h 10m	97%	86%
Delta Details →	HOU 06:00 → ATL 09:05DL 2557	2h 00m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 05m	97%	82%
Southwest Details →	HOU 07:00 → DAL 08:10WN 4	1h 55m Dallas	DAL 10:05 → MDW 12:20WN 1357	5h 20m	99%	79%
Southwest Details →	HOU 07:10 → BNA 09:10WN 1954	3h 45m Nashville	BNA 12:55 → MDW 14:30WN 1430	7h 20m	100%	78%
Southwest Details →	HOU 07:30 → MCI 09:25WN 1037	2h 13m Kansas City	MCI 11:38 → MDW 13:02WN 2571	5h 33m	96%	76%
Delta Details →	HOU 10:16 → ATL 13:20DL 1509	1h 55m Atlanta	ATL 15:15 → MDW 16:15DL 1728	5h 59m	96%	70%
Tight connection: often missed
Delta Details →	HOU 17:12 → ATL 20:28DL 2381	47m Atlanta	ATL 21:15 → MDW 22:17DL 1076	5h 05m	69%	51%
Southwest Details →	HOU 11:22 → MCO 14:52WN 2034	48m Orlando	MCO 15:40 → MDW 17:30WN 2658	6h 13m	63%	36%
Southwest Details →	HOU 14:55 → RDU 18:35WN 4411	53m Raleigh/Durham	RDU 19:28 → MDW 20:28WN 3766	5h 33m	29%	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

DAL · 55m · leaves 08:00 14%

DEN · 1h 10m · leaves 10:20 14%

OMA · 55m · leaves 07:50 21%

Afternoon and evening

PHX · 50m · leaves 14:25 57%

SAN · 50m · leaves 20:40 64%

RDU · 53m · leaves 14:55 71%

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 2622 HOU 05:50 → ATL Delta DL 2417 ATL 11:05 → MDW Connection details →	2h 15m	6h 15m	100%	86%
Delta DL 2557 HOU 06:00 → ATL Southwest WN 225 ATL 12:30 → MDW Connection details →	3h 25m	7h 25m	99%	74%
Southwest WN 1947 HOU 09:45 → ATL Delta DL 1728 ATL 15:15 → MDW Connection details →	2h 27m	6h 30m	96%	72%

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