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 7% of the time at 8 am and almost half the time at 8 pm.

Nonstops (seasonal or thin)


Southwest	MIA	MDW	3h 15m	68%	1.6%	439	Flying now
Frontier	MIA	MDW	3h 27m	79%	1.6%	64	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 Miami). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	MIA 05:25 → MCO 06:30WN 4086	1h 45m Orlando	MCO 08:15 → MDW 10:00WN 1340	5h 35m	96%	85%
Delta Details →	MIA 06:00 → ATL 08:05DL 1249	3h 00m Atlanta	ATL 11:05 → MDW 12:05DL 2417	7h 05m	99%	83%
Southwest Details →	MIA 05:10 → HOU 06:45WN 2927	1h 25m Houston	HOU 08:10 → MDW 10:40WN 1294	6h 30m	89%	74%
Delta Details →	MIA 16:00 → ATL 18:22DL 1579	2h 53m Atlanta	ATL 21:15 → MDW 22:17DL 1076	7h 17m	95%	71%
Delta Details →	MIA 10:40 → ATL 12:48DL 2836	2h 27m Atlanta	ATL 15:15 → MDW 16:15DL 1728	6h 35m	96%	71%
Southwest Details →	MIA 06:20 → BWI 08:55WN 974	3h 35m Baltimore	BWI 12:30 → MDW 13:30WN 435	8h 10m	100%	69%
Southwest Details →	MIA 07:15 → STL 09:05WN 2931	3h 35m St Louis	STL 12:40 → MDW 13:45WN 3344	7h 30m	100%	58%
Southwest Details →	MIA 15:20 → MCI 17:35WN 4925	2h 20m Kansas City	MCI 19:55 → MDW 21:20WN 345	7h 00m	93%	57%
Tight connection: often missed
Delta Details →	MIA 18:05 → ATL 20:22DL 1386	53m Atlanta	ATL 21:15 → MDW 22:17DL 1076	5h 12m	52%	38%
Frontier Details →	MIA 17:28 → ATL 20:00F9 4405	1h 00m Atlanta	ATL 21:00 → MDW 22:03F9 2291	5h 36m	57%	38%
Southwest Details →	MIA 17:00 → DAL 19:00WN 1374	50m Dallas	DAL 19:50 → MDW 22:00WN 107	6h 05m	23%	8%

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

ATL · 1h 04m · leaves 06:00 7%

Afternoon and evening

DTW · 1h 18m · leaves 13:38 11%

BWI · 1h 15m · leaves 15:05 33%

ATL · 53m · leaves 18:05 48%

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 2187 MIA 06:21 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	3h 00m	7h 14m	97%	92%
American AA 491 MIA 06:19 → DCA Southwest WN 1445 DCA 12:00 → MDW Connection details →	3h 00m	7h 41m	98%	84%
Delta DL 1249 MIA 06:00 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	1h 55m	6h 00m	94%	81%

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