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

The nonstop is quickest: United EWR → EYW (3h 31m), on time 4 times in 5. American via Miami (5h 24m) is more reliable, 92%, but takes 1h 53m longer.

Nonstops (seasonal or thin)


United	EWR	EYW	3h 31m	83%	2.0%	460	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

Ranked by chance you reach Key West on time. Total trip = scheduled departure to arrival, layover included. Layovers up to 4 hours. Pick a connection for the details.


American Details →	EWR 05:31 → MIA 08:45AA 1196	1h 10m Miami	MIA 09:55 → EYW 10:55AA 3515 · flown by Envoy	5h 24m	97%	92%
United + Americantwo ticketsDetails →	EWR 07:00 → MIA 10:02UA 2785	2h 08m Miami	MIA 12:10 → EYW 13:14AA 3518 · flown by Envoy	6h 14m	98%	84%
United + Americantwo ticketsDetails →	EWR 11:31 → MIA 14:38UA 2295	3h 33m Miami	MIA 18:11 → EYW 19:10AA 3517 · flown by Envoy	7h 41m	99%	84%
United + Deltatwo ticketsDetails →	EWR 06:00 → ATL 08:23UA 1012	3h 08m Atlanta	ATL 11:31 → EYW 13:28DL 1472	7h 24m	100%	84%
United Details →	EWR 06:00 → ORD 07:42UA 530	3h 13m Chicago	ORD 10:55 → EYW 15:19UA 3690 · flown by Republic	9h 19m	98%	82%
American Details →	EWR 05:00 → CLT 06:57AA 1113	3h 03m Charlotte	CLT 10:00 → EYW 12:14AA 1826	7h 14m	98%	74%
American Details →	EWR 06:56 → ORD 08:44AA 3267	2h 36m Chicago	ORD 11:20 → EYW 15:41AA 3996 · flown by Envoy	8h 45m	95%	74%
Delta Details →	EWR 10:31 → ATL 12:54DL 2325	2h 31m Atlanta	ATL 15:25 → EYW 17:23DL 2168	6h 52m	96%	72%

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

MIA · 1h 10m · leaves 05:31 3%

ORD · 1h 12m · leaves 07:59 10%

Afternoon and evening

CLT · 58m · leaves 13:30 21%

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