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 → RSW flights land within a few points of 77% on time whatever the hour.

Nonstops


Southwest	MDW	RSW	2h 45m	77%	1.5%	1,162	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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


Southwest Details →	MDW 07:50 → STL 09:10WN 2900	55m St Louis	STL 10:05 → RSW 13:35WN 4940	4h 45m	93%	82%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	3h 58m Atlanta	ATL 12:53 → RSW 14:35DL 1196	7h 34m	97%	79%
Delta Details →	MDW 09:17 → DTW 11:35DL 4674 · flown by Endeavor	2h 57m Detroit	DTW 14:32 → RSW 17:27DL 1225	7h 10m	98%	76%
Southwest Details →	MDW 10:05 → IND 12:08WN 3877	1h 32m Indianapolis	IND 13:40 → RSW 16:05WN 2137	5h 00m	99%	73%
Delta Details →	MDW 11:05 → ATL 14:01DL 1063	3h 06m Atlanta	ATL 17:07 → RSW 18:55DL 1124	6h 47m	99%	70%
Delta Details →	MDW 17:10 → ATL 20:22DL 1728	2h 53m Atlanta	ATL 23:15 → RSW 01:01 +1DL 1217	6h 51m	95%	68%
Delta Details →	MDW 12:50 → ATL 15:49DL 2417	3h 38m Atlanta	ATL 19:27 → RSW 21:12DL 1736	7h 22m	98%	64%
Delta Details →	MDW 09:54 → MSP 11:35DL 5469 · flown by Endeavor	1h 10m Minneapolis	MSP 12:45 → RSW 17:10DL 402	6h 16m	89%	61%
Tight connection: often missed
Southwest Details →	MDW 18:00 → STL 19:10WN 2904	50m St Louis	STL 20:00 → RSW 23:25WN 4831	4h 25m	57%	34%

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

STL · 55m · leaves 07:50 7%

MSP · 1h 10m · leaves 09:54 11%

Afternoon and evening

ATL · 1h 18m · leaves 12:50 11%

STL · 50m · leaves 18:00 43%

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.


Southwest WN 3054 MDW 07:15 → ATL Delta DL 1196 ATL 12:53 → RSW Connection details →	2h 48m	6h 19m	100%	84%
Southwest WN 4154 MDW 08:55 → ATL Delta DL 1379 ATL 14:54 → RSW Connection details →	3h 09m	6h 44m	100%	71%
Southwest WN 4976 MDW 06:00 → DCA American AA 2448 DCA 10:45 → RSW Connection details →	2h 00m	6h 23m	100%	70%

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