Itineraries flown on 20+ days in the Jun 6 – Jul 31, 2026 schedule · each leg’s record Aug 2025 – Jul 2026

No clear winner: airlines and hours on this route all land within a few points of 78% on time.

Nonstops


United	RSW	ORD	3h 21m	82%	0.7%	1,612	Flying now
American	RSW	ORD	3h 21m	76%	1.7%	1,143	Flying now
Spirit	RSW	ORD	3h 10m	71%	5.3%	337	Not flying now
Southwest	RSW	ORD	3h 20m	59%	1.9%	103	Not flying now
Frontier	RSW	ORD	3h 33m	71%few flights	2.8%	36	Not 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.


American Details →	RSW 06:22 → CLT 08:20AA 1097	2h 41m Charlotte	CLT 11:01 → ORD 12:19AA 2908	6h 57m	99%	88%
United Details →	RSW 07:00 → IAH 08:33UA 2773	1h 02m Houston	IAH 09:35 → ORD 12:29UA 2124	6h 29m	100%	85%
United Details →	RSW 06:02 → EWR 08:59UA 2455	2h 26m Newark	EWR 11:25 → ORD 13:08UA 1875	8h 06m	100%	74%
Delta Details →	RSW 08:03 → ATL 09:52DL 1395	3h 10m Atlanta	ATL 13:02 → ORD 14:16DL 1477	7h 13m	99%	74%
Delta Details →	RSW 05:37 → ATL 07:23DL 1385	1h 39m Atlanta	ATL 09:02 → ORD 10:13DL 1147	5h 36m	96%	73%
American Details →	RSW 10:00 → CLT 12:02AA 2427	2h 33m Charlotte	CLT 14:35 → ORD 15:56AA 2080	6h 56m	96%	69%
Delta Details →	RSW 06:45 → ATL 08:33DL 1361	2h 49m Atlanta	ATL 11:22 → ORD 12:36DL 2894	6h 51m	99%	68%
American Details →	RSW 07:01 → PHL 09:45AA 1240	50m Philadelphia	PHL 10:35 → ORD 12:09AA 1041	6h 08m	86%	68%
Tight connection: often missed
American Details →	RSW 18:24 → DCA 20:59AA 2454	1h 11m Washington	DCA 22:10 → ORD 23:30AA 4419 · flown by Republic	6h 06m	69%	43%
American Details →	RSW 12:06 → PHL 14:54AA 2445	51m Philadelphia	PHL 15:45 → ORD 17:29AA 470	6h 23m	66%	41%
American Details →	RSW 18:22 → DFW 20:24AA 2446	1h 48m Dallas-Fort Worth	DFW 22:12 → ORD 00:50 +1AA 1193	7h 28m	73%	35%

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

PHL · 50m · leaves 07:01 14%

Afternoon and evening

DFW · 1h 09m · leaves 14:25 23%

DCA · 1h 11m · leaves 18:24 31%

CLT · 54m · leaves 19:41 33%

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 4872 RSW 06:15 → MCO United UA 2683 MCO 09:40 → ORD Connection details →	2h 25m	6h 33m	100%	92%
Southwest WN 3471 RSW 06:00 → STL United UA 4517 STL 10:20 → ORD Connection details →	2h 50m	6h 52m	100%	89%
Southwest WN 3463 RSW 06:30 → BWI United UA 704 BWI 10:32 → ORD Connection details →	1h 42m	6h 18m	93%	84%

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