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 MDW → JAX flights land within a few points of 73% on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	MDW	JAX	2h 15m	73%	1.0%	416	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

Ranked by chance you reach Jacksonville on time. Total trip = scheduled departure to arrival, layover included (Jacksonville is 1 h ahead of Chicago). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	MDW 05:20 → AUS 07:50WN 2726	2h 50m Austin	AUS 10:40 → JAX 14:10WN 320	7h 50m	100%	88%
Southwest + Deltatwo ticketsDetails →	MDW 07:15 → ATL 10:05WN 3054	3h 52m Atlanta	ATL 13:57 → JAX 15:07DL 2990	6h 53m	100%	81%
Delta Details →	MDW 09:54 → MSP 11:35DL 5469 · flown by Endeavor	1h 22m Minneapolis	MSP 12:57 → JAX 16:54DL 2392	5h 58m	93%	79%
Delta Details →	MDW 09:17 → DTW 11:35DL 4674 · flown by Endeavor	3h 28m Detroit	DTW 15:03 → JAX 17:27DL 2994	7h 10m	98%	78%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	1h 53m Atlanta	ATL 10:48 → JAX 12:00DL 2923	5h 00m	94%	78%
Southwest + Deltatwo ticketsDetails →	MDW 08:55 → ATL 11:45WN 4154	3h 35m Atlanta	ATL 15:20 → JAX 16:33DL 2720	6h 38m	100%	77%
Frontier + Deltatwo ticketsDetails →	MDW 06:00 → ATL 09:19F9 2292	3h 14m Atlanta	ATL 12:33 → JAX 13:43DL 3024	6h 43m	98%	75%
Southwest + Unitedtwo ticketsDetails →	MDW 06:50 → DEN 08:20WN 2765	1h 45m Denver	DEN 10:05 → JAX 15:39UA 1451	7h 49m	84%	71%
Tight connection: often missed
Frontier Details →	MDW 12:11 → ATL 15:13F9 2144	1h 05m Atlanta	ATL 16:18 → JAX 17:34F9 1550	4h 23m	71%	37%
Southwest Details →	MDW 11:20 → BNA 12:45WN 2733	55m Nashville	BNA 13:40 → JAX 16:15WN 542	3h 55m	48%	22%

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 · 1h 05m · leaves 12:11 29%

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