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

Take the nonstop: Southwest MDW → MIA (3h 00m) reaches Miami on time 3 times in 4; the most reliable connection, Delta via Atlanta (4h 55m), 53%.

Nonstops (seasonal or thin)


Southwest	MDW	MIA	3h 00m	74%	1.1%	439	Flying now
Frontier	MDW	MIA	3h 13m	75%	1.6%	64	Not flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

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


Southwest + Americantwo ticketsDetails →	MDW 07:50 → STL 09:10WN 2900	1h 50m St Louis	STL 11:00 → MIA 14:46AA 3954 · flown by Envoy	5h 56m	95%	85%
Delta + Americantwo ticketsDetails →	MDW 13:26 → DTW 15:44DL 4688 · flown by Endeavor	3h 13m Detroit	DTW 18:57 → MIA 22:10AA 3358 · flown by Envoy	7h 44m	93%	84%
Southwest + Americantwo ticketsDetails →	MDW 05:10 → MCO 08:40WN 2815	2h 22m Orlando	MCO 11:02 → MIA 12:14AA 1712	6h 04m	100%	83%
Southwest + Americantwo ticketsDetails →	MDW 05:15 → LGA 08:15WN 2801	2h 54m New York	LGA 11:09 → MIA 14:21AA 3076	8h 06m	100%	83%
Southwest + Americantwo ticketsDetails →	MDW 07:40 → BOS 10:55WN 4611	2h 47m Boston	BOS 13:42 → MIA 17:22AA 1589	8h 37m	100%	78%
Southwest + Americantwo ticketsDetails →	MDW 06:00 → DCA 08:45WN 4976	3h 10m Washington	DCA 11:55 → MIA 14:38AA 1627	7h 38m	100%	76%
Southwest Details →	MDW 07:00 → BWI 09:45WN 2742	2h 00m Baltimore	BWI 11:45 → MIA 14:20WN 4737	6h 20m	94%	75%
Southwest + Deltatwo ticketsDetails →	MDW 07:15 → ATL 10:05WN 3054	2h 49m Atlanta	ATL 12:54 → MIA 14:55DL 1579	6h 40m	100%	75%

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

STL · 1h 00m · leaves 10:32 25%

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