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

Nonstops (seasonal or thin)


Southwest	DSM	MDW	1h 20m	81%	1.7%	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 →	DSM 06:10 → DEN 07:00WN 1769	3h 00m Denver	DEN 10:00 → MDW 13:25WN 755	7h 15m	97%	84%
Delta Details →	DSM 05:35 → ATL 08:44DL 2727	2h 21m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 30m	98%	82%
Delta Details →	DSM 06:08 → DTW 08:59DL 5414 · flown by Endeavor	3h 26m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	6h 38m	96%	76%
Delta Details →	DSM 14:25 → ATL 17:38DL 2094	3h 37m Atlanta	ATL 21:15 → MDW 22:17DL 1076	7h 52m	100%	75%
Delta Details →	DSM 06:50 → MSP 08:12DL 5402 · flown by Endeavor	3h 18m Minneapolis	MSP 11:30 → MDW 13:09DL 4820 · flown by Endeavor	6h 19m	96%	56%
Southwest Details →	DSM 12:05 → LAS 13:10WN 1771	2h 55m Las Vegas	LAS 16:05 → MDW 21:45WN 2274	9h 38m	100%	50%
Southwest Details →	DSM 13:30 → DEN 14:25WN 1770	3h 10m Denver	DEN 17:35 → MDW 21:00WN 1604	7h 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 4777 DSM 05:50 → DEN Southwest WN 755 DEN 10:00 → MDW Connection details →	3h 01m	7h 35m	95%	82%
American AA 3710 DSM 06:30 → DCA Southwest WN 1445 DCA 12:00 → MDW Connection details →	2h 01m	6h 30m	92%	78%
Delta DL 2727 DSM 05:35 → ATL Southwest WN 225 ATL 12:30 → MDW Connection details →	3h 46m	7h 50m	98%	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