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 New York on time 3 times in 4.

Best connections, any airlines

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


Southwest + Deltatwo ticketsDetails →	MDW 05:00 → TPA 08:25WN 2906	2h 43m Tampa	TPA 11:08 → JFK 13:59DL 2042	7h 59m	100%	85%
Southwest + Americantwo ticketsDetails →	MDW 07:45 → PIT 10:15WN 846	1h 58m Pittsburgh	PIT 12:13 → JFK 13:55AA 4568 · flown by Republic	5h 10m	100%	83%
Southwest + Deltatwo ticketsDetails →	MDW 07:40 → MSP 09:10WN 1243	3h 43m Minneapolis	MSP 12:53 → JFK 17:00DL 2661	8h 20m	100%	82%
Southwest + Deltatwo ticketsDetails →	MDW 05:10 → MCO 08:40WN 2815	2h 25m Orlando	MCO 11:05 → JFK 13:47DL 2049	7h 37m	100%	79%
Southwest + Deltatwo ticketsDetails →	MDW 07:45 → CMH 10:05WN 4093	2h 42m Columbus	CMH 12:47 → JFK 14:55DL 5649 · flown by Republic	6h 10m	100%	76%
Southwest + Deltatwo ticketsDetails →	MDW 07:15 → ATL 10:05WN 3054	3h 54m Atlanta	ATL 13:59 → JFK 16:28DL 1575	8h 13m	100%	76%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 15m Atlanta	ATL 11:10 → JFK 13:29DL 2380	6h 29m	95%	75%
Southwest + JetBluetwo ticketsDetails →	MDW 08:00 → MCO 11:35WN 2817	3h 22m Orlando	MCO 14:57 → JFK 17:44B6 1084	8h 51m	100%	73%

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

MSP · 1h 18m · leaves 09:54 8%

Afternoon and evening

ATL · 54m · leaves 12:50 18%

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