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

Nonstops


Southwest	BNA	MDW	1h 35m	76%	1.3%	1,894	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 →	BNA 06:15 → STL 07:35WN 679	1h 20m St Louis	STL 08:55 → MDW 10:00WN 2570	3h 45m	100%	87%
Southwest Details →	BNA 05:40 → DCA 08:25WN 4991	3h 35m Washington	DCA 12:00 → MDW 13:00WN 1445	7h 20m	100%	85%
Delta Details →	BNA 06:15 → ATL 08:31DL 3001	2h 34m Atlanta	ATL 11:05 → MDW 12:05DL 2417	5h 50m	99%	84%
Southwest Details →	BNA 05:02 → HOU 07:02WN 4430	1h 08m Houston	HOU 08:10 → MDW 10:40WN 1294	5h 38m	99%	83%
Delta Details →	BNA 05:10 → ATL 07:20DL 2637	1h 49m Atlanta	ATL 09:09 → MDW 10:09DL 1063	4h 59m	97%	80%
Southwest Details →	BNA 08:10 → MCI 09:50WN 4289	1h 48m Kansas City	MCI 11:38 → MDW 13:02WN 2571	4h 53m	100%	80%
Southwest Details →	BNA 05:10 → DAL 07:00WN 485	3h 05m Dallas	DAL 10:05 → MDW 12:20WN 1357	7h 10m	100%	79%
Delta Details →	BNA 06:05 → DTW 08:49DL 2439	3h 36m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	6h 41m	98%	79%
Tight connection: often missed
Southwest Details →	BNA 16:30 → CMH 18:50WN 481	1h 18m Columbus	CMH 20:08 → MDW 20:22WN 1200	3h 53m	64%	39%
Southwest Details →	BNA 14:45 → PHL 17:50WN 626	1h 05m Philadelphia	PHL 18:55 → MDW 20:20WN 3226	5h 35m	51%	28%
Southwest Details →	BNA 14:55 → MCO 18:00WN 569	55m Orlando	MCO 18:55 → MDW 20:50WN 2660	5h 55m	46%	17%

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

MCO · 1h 10m · leaves 05:10 0%

STL · 1h 20m · leaves 06:15 0%

HOU · 1h 08m · leaves 05:02 1%

Afternoon and evening

PHL · 1h 05m · leaves 14:45 49%

MCO · 55m · leaves 14:55 54%

TPA · 55m · leaves 18:45 69%

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 1065 BNA 05:31 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	3h 35m	7h 04m	100%	95%
Delta DL 2637 BNA 05:10 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	2h 40m	5h 50m	97%	84%
Delta DL 5708 BNA 06:05 → DCA Southwest WN 1445 DCA 12:00 → MDW Connection details →	2h 58m	6h 55m	96%	81%

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