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 LGA → MDW flights land within a few points of 3 in 4 on time whatever the hour.

Nonstops


Southwest	LGA	MDW	2h 30m	74%	4.9%	2,385	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 New York). Layovers up to 4 hours. Pick a connection for the details.


Delta Details →	LGA 06:00 → ATL 08:15DL 550	2h 50m Atlanta	ATL 11:05 → MDW 12:05DL 2417	7h 05m	98%	81%
Southwest Details →	LGA 06:30 → MCI 08:30WN 576	3h 08m Kansas City	MCI 11:38 → MDW 13:02WN 2571	7h 33m	98%	78%
Southwest Details →	LGA 06:05 → DAL 08:35WN 2341	1h 30m Dallas	DAL 10:05 → MDW 12:20WN 1357	7h 15m	96%	75%
Delta Details →	LGA 10:00 → ATL 12:27DL 989	2h 48m Atlanta	ATL 15:15 → MDW 16:15DL 1728	7h 15m	98%	72%
Delta Details →	LGA 09:25 → DTW 11:25DL 1078	1h 00m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	4h 21m	90%	71%
Delta Details →	LGA 15:00 → ATL 17:53DL 974	3h 22m Atlanta	ATL 21:15 → MDW 22:17DL 1076	8h 17m	96%	70%
Southwest Details →	LGA 06:55 → DEN 09:05WN 2454	55m Denver	DEN 10:00 → MDW 13:25WN 755	7h 30m	80%	69%
Delta Details →	LGA 06:05 → DTW 07:54DL 1231	56m Detroit	DTW 08:50 → MDW 09:14DL 4684 · flown by Endeavor	4h 09m	95%	67%
Tight connection: often missed
Southwest Details →	LGA 18:30 → STL 20:30WN 4895	1h 15m St Louis	STL 21:45 → MDW 22:55WN 3957	5h 20m	64%	35%
Frontier Details →	LGA 06:29 → ATL 09:17F9 3287	48m Atlanta	ATL 10:05 → MDW 11:07F9 2779	5h 40m	46%	27%
Southwest Details →	LGA 14:00 → DEN 16:20WN 2455	1h 15m Denver	DEN 17:35 → MDW 21:00WN 1604	8h 00m	67%	17%

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

DTW · 56m · leaves 06:05 5%

ATL · 54m · leaves 06:00 13%

DEN · 55m · leaves 06:55 20%

Afternoon and evening

DEN · 1h 15m · leaves 14:00 33%

STL · 1h 15m · leaves 18:30 36%

BNA · 1h 00m · leaves 17:30 47%

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.


American AA 3084 LGA 06:00 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	3h 37m	7h 35m	98%	93%
American AA 4491 LGA 07:43 → DCA Southwest WN 1445 DCA 12:00 → MDW Connection details →	2h 47m	6h 17m	100%	85%
American AA 4398 LGA 06:45 → CMH Southwest WN 4386 CMH 11:55 → MDW Connection details →	3h 16m	6h 25m	100%	83%

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