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

No clear winner: Southwest’s MDW → LGA flights land within a few points of 7 in 10 on time whatever the hour.

Nonstops


Southwest	MDW	LGA	2h 05m	70%	4.2%	2,385	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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.


Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 35m Atlanta	ATL 11:30 → LGA 13:44DL 467	6h 44m	95%	78%
Southwest Details →	MDW 08:00 → MCI 09:30WN 2808	1h 45m Kansas City	MCI 11:15 → LGA 15:00WN 2563	6h 00m	100%	73%
Southwest Details →	MDW 07:50 → STL 09:10WN 2900	1h 50m St Louis	STL 11:00 → LGA 14:25WN 1373	5h 35m	96%	72%
Delta Details →	MDW 09:54 → MSP 11:35DL 5469 · flown by Endeavor	1h 25m Minneapolis	MSP 13:00 → LGA 16:45DL 2756	5h 51m	95%	71%
Delta Details →	MDW 09:17 → DTW 11:35DL 4674 · flown by Endeavor	2h 27m Detroit	DTW 14:02 → LGA 15:55DL 2602	5h 38m	96%	71%
Southwest Details →	MDW 10:10 → OMA 11:35WN 2984	1h 30m Omaha	OMA 13:05 → LGA 16:55WN 2294	5h 45m	94%	68%
Delta Details →	MDW 11:05 → ATL 14:01DL 1063	1h 29m Atlanta	ATL 15:30 → LGA 17:49DL 433	5h 44m	94%	64%
Delta Details →	MDW 12:50 → ATL 15:49DL 2417	3h 11m Atlanta	ATL 19:00 → LGA 21:25DL 468	7h 35m	98%	61%
Tight connection: often missed
Southwest Details →	MDW 07:15 → BNA 08:40WN 2959	1h 05m Nashville	BNA 09:45 → LGA 13:05WN 1966	4h 50m	71%	45%
Southwest Details →	MDW 14:30 → DEN 16:10WN 2768	1h 05m Denver	DEN 17:15 → LGA 23:00WN 4480	7h 30m	57%	14%

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

BNA · 1h 05m · leaves 07:15 29%

Afternoon and evening

ATL · 1h 11m · leaves 12:50 12%

DEN · 1h 05m · leaves 14:30 43%

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 2906 MDW 05:00 → TPA Delta DL 2531 TPA 11:07 → LGA Connection details →	2h 42m	7h 53m	100%	90%
Southwest WN 2749 MDW 07:50 → CLT American AA 2036 CLT 13:07 → LGA Connection details →	2h 12m	6h 15m	100%	81%
Southwest WN 846 MDW 07:45 → PIT Delta DL 5694 PIT 13:00 → LGA Connection details →	2h 45m	5h 52m	100%	80%

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