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 4 in 5 on time.

Nonstops (seasonal or thin)


American	ORD	EYW	3h 26m	82%	1.4%	435	Flying now
United	ORD	EYW	3h 24m	80%	1.5%	340	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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


American Details →	ORD 10:04 → MIA 14:16AA 1474	3h 55m Miami	MIA 18:11 → EYW 19:10AA 3517 · flown by Envoy	8h 08m	100%	87%
American Details →	ORD 05:00 → MIA 09:09AA 2984	3h 01m Miami	MIA 12:10 → EYW 13:14AA 3518 · flown by Envoy	7h 14m	100%	87%
Delta Details →	ORD 05:30 → ATL 08:33DL 1264	2h 58m Atlanta	ATL 11:31 → EYW 13:28DL 1472	6h 54m	98%	83%
American Details →	ORD 08:00 → CLT 11:08AA 3222	2h 42m Charlotte	CLT 13:50 → EYW 16:11AA 3519 · flown by Envoy	7h 11m	97%	82%
American Details →	ORD 05:00 → PHL 08:05AA 2970	2h 25m Philadelphia	PHL 10:30 → EYW 13:41AA 1898	7h 40m	94%	78%
Delta Details →	ORD 09:45 → ATL 12:51DL 1178	2h 34m Atlanta	ATL 15:25 → EYW 17:23DL 2168	6h 38m	99%	76%
United Details →	ORD 06:00 → EWR 09:12UA 2295	1h 06m Newark	EWR 10:18 → EYW 13:30UA 1418	6h 30m	94%	74%
Delta Details →	ORD 11:23 → ATL 14:25DL 1147	3h 28m Atlanta	ATL 17:53 → EYW 19:53DL 2815	7h 30m	98%	72%
Tight connection: often missed
Delta Details →	ORD 13:46 → ATL 16:54DL 2894	59m Atlanta	ATL 17:53 → EYW 19:53DL 2815	5h 07m	72%	55%

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

EWR · 1h 06m · leaves 06:00 6%

MIA · 46m · leaves 05:00 20%

Afternoon and evening

ATL · 59m · leaves 13:46 28%

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.


United UA 1620 ORD 10:33 → MIA American AA 3517 MIA 18:11 → EYW Connection details →	3h 14m	7h 39m	97%	84%
United UA 530 ORD 09:07 → ATL Delta DL 2168 ATL 15:25 → EYW Connection details →	3h 03m	7h 16m	97%	74%
United UA 539 ORD 07:15 → DFW American AA 1814 DFW 13:02 → EYW Connection details →	3h 04m	8h 39m	97%	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