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 OMA → MDW flights land within a few points of 82% on time whatever the hour.

Nonstops


Southwest	OMA	MDW	1h 25m	82%	1.4%	1,327	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 →	OMA 06:15 → DEN 06:50WN 3127	3h 10m Denver	DEN 10:00 → MDW 13:25WN 755	7h 10m	98%	84%
Delta Details →	OMA 05:46 → ATL 08:59DL 1136	2h 06m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 19m	97%	82%
Delta Details →	OMA 06:25 → DTW 09:30DL 4110 · flown by SkyWest	2h 55m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	6h 21m	97%	78%
Southwest Details →	OMA 21:20 → PHX 22:00WN 3137	1h 55m Phoenix	PHX 23:55 → MDW 05:10 +1WN 3298	7h 50m	90%	75%
Southwest Details →	OMA 06:00 → LAS 06:50WN 2340	1h 30m Las Vegas	LAS 08:20 → MDW 13:55WN 2271	7h 55m	98%	73%
Delta Details →	OMA 10:40 → ATL 13:53DL 2632	1h 22m Atlanta	ATL 15:15 → MDW 16:15DL 1728	5h 35m	93%	69%
Southwest Details →	OMA 17:15 → STL 18:30WN 3365	3h 15m St Louis	STL 21:45 → MDW 22:55WN 3957	5h 35m	100%	67%
Southwest Details →	OMA 07:55 → STL 09:10WN 3139	3h 30m St Louis	STL 12:40 → MDW 13:45WN 3344	5h 50m	100%	58%
Tight connection: often missed
Southwest Details →	OMA 17:25 → HOU 19:45WN 3129	1h 00m Houston	HOU 20:45 → MDW 23:10WN 2044	5h 45m	73%	27%

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

ATL · 49m · leaves 07:01 12%

Afternoon and evening

DTW · 57m · leaves 14:05 23%

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.


United UA 1442 OMA 06:00 → DEN Southwest WN 755 DEN 10:00 → MDW Connection details →	3h 11m	7h 25m	99%	86%
American AA 1042 OMA 06:20 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	1h 37m	6h 15m	90%	86%
Delta DL 3864 OMA 06:15 → MSP Southwest WN 4345 MSP 10:25 → MDW Connection details →	2h 50m	5h 40m	96%	76%

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