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

Nonstops


Southwest	RSW	MDW	2h 55m	75%	1.6%	1,161	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 (Chicago is 1 h behind Fort Myers). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	RSW 06:25 → DEN 08:20WN 1739	1h 40m Denver	DEN 10:00 → MDW 13:25WN 755	8h 00m	100%	87%
Southwest Details →	RSW 06:15 → MCO 07:15WN 4872	1h 00m Orlando	MCO 08:15 → MDW 10:00WN 1340	4h 45m	100%	87%
Southwest Details →	RSW 06:00 → STL 07:30WN 3471	1h 25m St Louis	STL 08:55 → MDW 10:00WN 2570	5h 00m	98%	87%
Delta Details →	RSW 06:45 → ATL 08:33DL 1361	2h 32m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 20m	98%	84%
Delta Details →	RSW 05:37 → ATL 07:23DL 1385	1h 46m Atlanta	ATL 09:09 → MDW 10:09DL 1063	5h 32m	96%	80%
Delta Details →	RSW 15:41 → ATL 17:34DL 1196	3h 41m Atlanta	ATL 21:15 → MDW 22:17DL 1076	7h 36m	98%	72%
Delta Details →	RSW 10:48 → ATL 12:27DL 1089	2h 48m Atlanta	ATL 15:15 → MDW 16:15DL 1728	6h 27m	98%	72%
Southwest Details →	RSW 06:30 → BWI 08:50WN 3463	3h 40m Baltimore	BWI 12:30 → MDW 13:30WN 435	8h 00m	100%	69%
Tight connection: often missed
Southwest Details →	RSW 19:20 → STL 20:55WN 3472	50m St Louis	STL 21:45 → MDW 22:55WN 3957	4h 30m	33%	22%
Southwest Details →	RSW 16:45 → PIT 19:15WN 3470	55m Pittsburgh	PIT 20:10 → MDW 20:40WN 4073	4h 55m	26%	18%

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 00m · leaves 06:15 0%

ATL · 1h 13m · leaves 08:03 6%

Afternoon and evening

STL · 50m · leaves 19:20 67%

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 1097 RSW 06:22 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	3h 15m	7h 13m	99%	95%
Delta DL 1385 RSW 05:37 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	2h 37m	6h 23m	96%	84%
Delta DL 1361 RSW 06:45 → ATL Southwest WN 225 ATL 12:30 → MDW Connection details →	3h 57m	7h 40m	99%	75%

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