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

Nonstops (seasonal or thin)


Southwest	JAX	MDW	2h 28m	80%	1.4%	416	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 (Chicago is 1 h behind Jacksonville). Layovers up to 4 hours. Pick a connection for the details.


American + Southwesttwo ticketsDetails →	JAX 06:19 → CLT 07:46AA 1834	3h 49m Charlotte	CLT 11:35 → MDW 12:35WN 4529	7h 16m	99%	95%
Delta + Southwesttwo ticketsDetails →	JAX 05:30 → ATL 06:42DL 2722	3h 18m Atlanta	ATL 10:00 → MDW 11:00WN 224	6h 30m	98%	86%
Delta Details →	JAX 07:00 → ATL 08:15DL 2450	2h 50m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 05m	99%	82%
Southwest Details →	JAX 05:35 → HOU 06:50WN 2162	1h 20m Houston	HOU 08:10 → MDW 10:40WN 1294	6h 05m	100%	81%
American + Southwesttwo ticketsDetails →	JAX 07:00 → PHL 09:14AA 709	2h 08m Philadelphia	PHL 11:22 → MDW 12:32WN 3224	6h 32m	95%	80%
Delta + Southwesttwo ticketsDetails →	JAX 06:15 → LGA 08:38DL 5797 · flown by Republic	2h 17m New York	LGA 10:55 → MDW 12:15WN 4573	7h 00m	94%	78%
Delta Details →	JAX 10:41 → ATL 11:56DL 2326	3h 19m Atlanta	ATL 15:15 → MDW 16:15DL 1728	6h 34m	100%	74%
Delta + Southwesttwo ticketsDetails →	JAX 08:20 → ATL 09:36DL 2569	2h 54m Atlanta	ATL 12:30 → MDW 13:25WN 225	6h 05m	97%	74%
Tight connection: often missed
Delta Details →	JAX 19:04 → ATL 20:29DL 2627	46m Atlanta	ATL 21:15 → MDW 22:17DL 1076	4h 13m	67%	50%
Southwest Details →	JAX 17:20 → DEN 18:50WN 2161	2h 00m Denver	DEN 20:50 → MDW 00:15 +1WN 1615	7h 52m	67%	24%
Frontier Details →	JAX 18:29 → ATL 20:12F9 3083	48m Atlanta	ATL 21:00 → MDW 22:03F9 2291	4h 35m	24%	16%

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 · 54m · leaves 07:00 14%

Afternoon and evening

ATL · 48m · leaves 18:29 76%

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