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 ICT → MDW flights land within a few points of 88% on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	ICT	MDW	1h 50m	88%	1.0%	290	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 →	ICT 06:25 → DEN 06:55WN 4090	3h 05m Denver	DEN 10:00 → MDW 13:25WN 755	7h 00m	98%	86%
Delta Details →	ICT 05:43 → ATL 08:59DL 2216	2h 06m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 22m	99%	83%
Delta Details →	ICT 11:12 → ATL 14:26DL 1637	49m Atlanta	ATL 15:15 → MDW 16:15DL 1728	5h 03m	78%	58%
Delta Details →	ICT 07:23 → MSP 09:24DL 3542 · flown by SkyWest	2h 06m Minneapolis	MSP 11:30 → MDW 13:09DL 4820 · flown by Endeavor	5h 46m	95%	56%
Southwest Details →	ICT 12:40 → LAS 13:15WN 2104	2h 50m Las Vegas	LAS 16:05 → MDW 21:45WN 2274	9h 03m	98%	49%
Southwest Details →	ICT 14:30 → DEN 15:00WN 4644	2h 35m Denver	DEN 17:35 → MDW 21:00WN 1604	6h 30m	100%	27%

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.


United UA 5355 ICT 06:08 → DEN Southwest WN 755 DEN 10:00 → MDW Connection details →	3h 07m	7h 17m	97%	84%
Delta DL 2216 ICT 05:43 → ATL Southwest WN 225 ATL 12:30 → MDW Connection details →	3h 31m	7h 42m	99%	74%
American AA 3789 ICT 09:36 → DFW Frontier F9 2882 DFW 14:30 → MDW Connection details →	3h 26m	7h 18m	100%	64%

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