tailodds FORECAST
Tickets
Any day
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)

Nonstop details →
United EYW ORD 3h 48m 71% 1.8% 340 Flying now
American EYW ORD 3h 47m 69% 1.4% 435 Flying now

Best connections, any airlines

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 + Unitedtwo ticketsDetails → EYW 07:50 → ATL 09:56DL 1072 3h 22m Atlanta ATL 13:18 → ORD 14:41UA 745 7h 51m 96% 75%
American + Unitedtwo ticketsDetails → EYW 13:01 → CLT 15:25AA 1826 3h 15m Charlotte CLT 18:40 → ORD 20:18UA 5751 · flown by SkyWest 8h 17m 97% 67%
AmericanDetails → EYW 11:28 → MIA 12:20AA 3515 · flown by Envoy 2h 17m Miami MIA 14:37 → ORD 17:18AA 2247 6h 51m 100% 67%
DeltaDetails → EYW 18:18 → ATL 20:32DL 2168 2h 18m Atlanta ATL 22:50 → ORD 23:53DL 1199 6h 41m 96% 65%
UnitedDetails → EYW 14:26 → EWR 17:37UA 1513 2h 42m Newark EWR 20:19 → ORD 22:06UA 546 8h 40m 93% 61%
DeltaDetails → EYW 14:28 → ATL 16:36DL 1472 2h 39m Atlanta ATL 19:15 → ORD 20:33DL 2486 7h 04m 98% 60%
AmericanDetails → EYW 12:18 → DCA 15:17AA 4416 · flown by Republic 2h 05m Washington DCA 17:22 → ORD 18:54AA 1630 7h 36m 95% 59%
AmericanDetails → 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%
Tight connection: often missed
AmericanDetails → EYW 13:01 → CLT 15:25AA 1826 53m Charlotte CLT 16:18 → ORD 17:42AA 536 5h 40m 69% 46%
AmericanDetails → EYW 14:21 → DFW 16:33AA 305 1h 02m Dallas-Fort Worth DFW 17:35 → ORD 20:29AA 1893 7h 09m 73% 27%
AmericanDetails → 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.

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