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

Connect in the morning. The same one-hour layover misses 4% of the time at 11 am and 1 time in 4 at 8 pm.

Nonstops


United	SJU	ORD	5h 19m	82%	0.6%	665	Flying now
American	SJU	ORD	5h 32m	77%	2.1%	426	Flying now
Frontier	SJU	ORD	5h 13m	61%	4.8%	42	Flying now
Spirit	SJU	ORD	5h 16m	78%	6.9%	261	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 San Juan). Layovers up to 4 hours. Pick a connection for the details.


United Details →	SJU 02:05 → IAH 06:01UA 2495	2h 04m Houston	IAH 08:05 → ORD 11:01UA 1617	9h 56m	98%	89%
United Details →	SJU 01:00 → EWR 05:10UA 2219	2h 49m Newark	EWR 07:59 → ORD 09:43UA 2488	9h 43m	95%	80%
United Details →	SJU 07:20 → IAD 11:21UA 2022	1h 54m Dulles	IAD 13:15 → ORD 14:29UA 2331	8h 09m	100%	80%
American Details →	SJU 00:58 → DFW 05:00AA 2742	3h 30m Dallas-Fort Worth	DFW 08:30 → ORD 11:10AA 1059	11h 12m	99%	79%
Delta Details →	SJU 06:00 → ATL 09:50DL 1879	3h 12m Atlanta	ATL 13:02 → ORD 14:16DL 1477	9h 16m	100%	74%
United Details →	SJU 16:55 → IAD 20:56UA 2024	1h 24m Dulles	IAD 22:20 → ORD 23:31UA 1738	7h 36m	93%	73%
American Details →	SJU 06:00 → MIA 08:55AA 2817	3h 26m Miami	MIA 12:21 → ORD 14:57AA 2910	9h 57m	99%	70%
American Details →	SJU 07:00 → PHL 11:04AA 3063	1h 38m Philadelphia	PHL 12:42 → ORD 14:15AA 2925	8h 15m	96%	70%
Tight connection: often missed
American Details →	SJU 15:40 → CLT 19:39AA 783	48m Charlotte	CLT 20:27 → ORD 22:00AA 627	7h 20m	75%	44%

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

IAH · 1h 02m · leaves 07:00 4%

DFW · 1h 00m · leaves 00:58 9%

FLL · 1h 00m · leaves 06:00 17%

Afternoon and evening

DEN · 55m · leaves 13:40 16%

MIA · 1h 20m · leaves 16:38 18%

CLT · 48m · leaves 15:40 25%

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 3721 SJU 05:00 → MCO United UA 2466 MCO 10:52 → ORD Connection details →	2h 52m	9h 02m	100%	92%
Frontier F9 1823 SJU 03:10 → MCO United UA 2683 MCO 09:40 → ORD Connection details →	3h 30m	9h 38m	99%	91%
Southwest WN 3722 SJU 06:25 → MCO American AA 2067 MCO 11:38 → ORD Connection details →	2h 08m	8h 20m	100%	90%

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