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

No nonstop, and no clear pattern: the best connection reaches Chicago on time 84% of the time.

Best connections, any airlines

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


American + Southwesttwo ticketsDetails →	JFK 05:59 → CLT 07:57AA 2643	3h 38m Charlotte	CLT 11:35 → MDW 12:35WN 4529	7h 36m	98%	93%
Delta Details →	JFK 06:00 → ATL 08:24DL 2286	2h 41m Atlanta	ATL 11:05 → MDW 12:05DL 2417	7h 05m	99%	84%
American + Southwesttwo ticketsDetails →	JFK 11:52 → IND 14:15AA 4385 · flown by Republic	3h 25m Indianapolis	IND 17:40 → MDW 17:55WN 961	7h 03m	97%	78%
Delta Details →	JFK 07:15 → DTW 09:25DL 5080 · flown by Endeavor	3h 00m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	6h 31m	98%	77%
Delta + Southwesttwo ticketsDetails →	JFK 08:35 → DCA 10:02DL 5750 · flown by Republic	1h 58m Washington	DCA 12:00 → MDW 13:00WN 1445	5h 25m	94%	77%
Delta + Southwesttwo ticketsDetails →	JFK 07:44 → BNA 09:20DL 4919 · flown by Endeavor	3h 35m Nashville	BNA 12:55 → MDW 14:30WN 1430	7h 46m	99%	75%
American + Southwesttwo ticketsDetails →	JFK 12:30 → CLE 14:25AA 4453 · flown by Republic	2h 20m Cleveland	CLE 16:45 → MDW 17:05WN 1162	5h 35m	93%	70%
JetBlue + Deltatwo ticketsDetails →	JFK 15:08 → ATL 17:38B6 419	3h 37m Atlanta	ATL 21:15 → MDW 22:17DL 1076	8h 09m	95%	69%

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