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 7 in 10 on time.

Nonstops (seasonal or thin)


United	EYW	ORD	3h 48m	71%	1.8%	340	Flying now
American	EYW	ORD	3h 47m	69%	1.4%	435	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 Key West). Layovers up to 4 hours. Pick a connection for the details.


Delta Details →	EYW 07:50 → ATL 09:56DL 1072	3h 06m Atlanta	ATL 13:02 → ORD 14:16DL 1477	7h 26m	97%	72%
American Details →	EYW 11:28 → MIA 12:20AA 3515 · flown by Envoy	2h 17m Miami	MIA 14:37 → ORD 17:18AA 2247	6h 51m	100%	67%
Delta Details →	EYW 18:18 → ATL 20:32DL 2168	2h 18m Atlanta	ATL 22:50 → ORD 23:53DL 1199	6h 41m	96%	65%
United Details →	EYW 14:26 → EWR 17:37UA 1513	2h 42m Newark	EWR 20:19 → ORD 22:06UA 546	8h 40m	93%	61%
Delta Details →	EYW 14:28 → ATL 16:36DL 1472	2h 39m Atlanta	ATL 19:15 → ORD 20:33DL 2486	7h 04m	98%	60%
American Details →	EYW 12:18 → DCA 15:17AA 4416 · flown by Republic	2h 05m Washington	DCA 17:22 → ORD 18:54AA 1630	7h 36m	95%	59%
American Details →	EYW 16:44 → CLT 19:16AA 3519 · flown by Envoy	3h 23m Charlotte	CLT 22:39 → ORD 00:01 +1AA 3014	8h 17m	99%	58%
American Details →	EYW 13:47 → MIA 14:40AA 3518 · flown by Envoy	2h 20m Miami	MIA 17:00 → ORD 19:53AA 3056	7h 06m	98%	58%
Tight connection: often missed
American Details →	EYW 13:01 → CLT 15:25AA 1826	53m Charlotte	CLT 16:18 → ORD 17:42AA 536	5h 40m	69%	46%
American Details →	EYW 14:21 → DFW 16:33AA 305	1h 02m Dallas-Fort Worth	DFW 17:35 → ORD 20:29AA 1893	7h 09m	73%	27%
American Details →	EYW 17:34 → PHL 20:40AA 3147	52m Philadelphia	PHL 21:32 → ORD 23:30AA 3042	6h 56m	49%	26%

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

DFW · 1h 02m · leaves 14:21 27%

CLT · 53m · leaves 13:01 31%

PHL · 52m · leaves 17:34 51%

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.


Delta DL 1072 EYW 07:50 → ATL United UA 745 ATL 13:18 → ORD Connection details →	3h 22m	7h 51m	96%	75%
American AA 1826 EYW 13:01 → CLT United UA 5751 CLT 18:40 → ORD Connection details →	3h 15m	8h 17m	97%	67%
American AA 3515 EYW 11:28 → MIA United UA 2106 MIA 16:10 → ORD Connection details →	3h 50m	8h 25m	100%	58%

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