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 DAL → ORD flights land within a few points of 3 in 4 on time whatever the hour.

Nonstops (none in the current schedule)


Southwest	DAL	ORD	2h 25m	75%	0.9%	450	Not flying now

Best connections, any airlines

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 + Americantwo ticketsDetails →	DAL 06:05 → MCO 09:45WN 1434	1h 53m Orlando	MCO 11:38 → ORD 13:45AA 2067	7h 40m	100%	91%
Southwest + Americantwo ticketsDetails →	DAL 06:05 → LAS 06:50WN 1318	2h 50m Las Vegas	LAS 09:40 → ORD 15:42AA 2020	9h 37m	100%	90%
Southwest + Unitedtwo ticketsDetails →	DAL 06:10 → TPA 09:35WN 1415	2h 55m Tampa	TPA 12:30 → ORD 14:40UA 2223	8h 30m	100%	85%
Southwest + Unitedtwo ticketsDetails →	DAL 06:05 → MCI 07:35WN 4631	1h 59m Kansas City	MCI 09:34 → ORD 11:29UA 5504 · flown by SkyWest	5h 24m	95%	84%
Southwest + Unitedtwo ticketsDetails →	DAL 06:00 → DEN 07:00WN 1296	2h 35m Denver	DEN 09:35 → ORD 13:15UA 2329	7h 15m	100%	83%
Southwest + Unitedtwo ticketsDetails →	DAL 06:10 → DCA 10:00WN 3351	1h 57m Washington	DCA 11:57 → ORD 13:15UA 374	7h 05m	98%	82%
Southwest + Americantwo ticketsDetails →	DAL 06:00 → PHX 06:28WN 1379	2h 02m Phoenix	PHX 08:30 → ORD 14:21AA 319	8h 21m	100%	82%
Southwest + Unitedtwo ticketsDetails →	DAL 06:00 → MCO 09:40WN 1348	2h 54m Orlando	MCO 12:34 → ORD 14:42UA 2475	8h 42m	100%	81%
Tight connection: often missed
Delta Details →	DAL 18:40 → ATL 22:00DL 2780	50m Atlanta	ATL 22:50 → ORD 23:53DL 1199	5h 19m	72%	48%

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.

Afternoon and evening

ATL · 50m · leaves 18:40 28%

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.

The table above includes two-ticket connections (marked “two tickets”), held to the 90-minute minimum. One ticket only →

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