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 MCI → MDW flights land within a few points of 4 in 5 on time whatever the hour.

Nonstops


Southwest	MCI	MDW	1h 25m	81%	1.1%	2,107	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 →	MCI 06:50 → AUS 08:40WN 2528	1h 45m Austin	AUS 10:25 → MDW 12:55WN 4077	6h 05m	100%	88%
Southwest Details →	MCI 06:55 → DEN 07:45WN 2546	2h 15m Denver	DEN 10:00 → MDW 13:25WN 755	6h 30m	100%	87%
Delta Details →	MCI 05:38 → ATL 08:44DL 1204	2h 21m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 27m	99%	84%
Southwest Details →	MCI 06:05 → LGA 09:50WN 4862	1h 05m New York	LGA 10:55 → MDW 12:15WN 4573	6h 10m	96%	82%
Delta Details →	MCI 06:25 → DTW 09:25DL 1256	3h 00m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	6h 21m	100%	79%
Southwest Details →	MCI 13:30 → IND 16:00WN 1432	1h 40m Indianapolis	IND 17:40 → MDW 17:55WN 961	4h 25m	96%	79%
Southwest Details →	MCI 06:10 → DAL 07:45WN 4188	2h 20m Dallas	DAL 10:05 → MDW 12:20WN 1357	6h 10m	100%	79%
Southwest Details →	MCI 05:10 → TPA 08:45WN 4796	2h 00m Tampa	TPA 10:45 → MDW 12:25WN 4033	7h 15m	100%	78%
Tight connection: often missed
Southwest Details →	MCI 19:25 → DAL 20:55WN 2540	1h 27m Dallas	DAL 22:22 → MDW 01:00 +1WN 1359	5h 12m	74%	24%
Southwest Details →	MCI 17:30 → BNA 19:05WN 4269	1h 20m Nashville	BNA 20:25 → MDW 21:55WN 4286	4h 25m	63%	18%
Southwest Details →	MCI 17:25 → LAS 18:25WN 4240	55m Las Vegas	LAS 19:20 → MDW 01:30 +1WN 3200	7h 30m	38%	11%

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

LGA · 1h 05m · leaves 06:05 4%

PHX · 55m · leaves 05:50 5%

ATL · 1h 01m · leaves 07:00 6%

Afternoon and evening

DTW · 57m · leaves 14:10 13%

BNA · 1h 20m · leaves 17:30 37%

LAS · 55m · leaves 17:25 62%

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.


American AA 1297 MCI 06:31 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	1h 35m	6h 04m	91%	86%
United UA 355 MCI 06:00 → DEN Southwest WN 755 DEN 10:00 → MDW Connection details →	3h 04m	7h 25m	98%	84%
Delta DL 1635 MCI 06:23 → MSP Southwest WN 4345 MSP 10:25 → MDW Connection details →	2h 31m	5h 32m	97%	77%

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