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, one ticket

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 Details →	MDW 07:00 → BWI 09:45WN 2742	2h 00m Baltimore	BWI 11:45 → MIA 14:20WN 4737	6h 20m	94%	75%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 05m Atlanta	ATL 11:00 → MIA 13:04DL 1332	6h 04m	95%	75%
Southwest Details →	MDW 07:45 → CMH 10:05WN 4093	3h 45m Columbus	CMH 13:50 → MIA 16:25WN 114	7h 40m	100%	73%
Delta Details →	MDW 09:17 → DTW 11:35DL 4674 · flown by Endeavor	3h 08m Detroit	DTW 14:43 → MIA 18:04DL 866	7h 47m	98%	72%
Frontier Details →	MDW 06:00 → ATL 09:19F9 2292	2h 28m Atlanta	ATL 11:47 → MIA 13:53F9 4406	6h 49m	98%	70%
Southwest Details →	MDW 13:40 → MCO 17:30WN 2819	3h 20m Orlando	MCO 20:50 → MIA 22:05WN 1516	7h 25m	100%	69%
Delta Details →	MDW 13:49 → MSP 15:33DL 4820 · flown by Endeavor	3h 18m Minneapolis	MSP 18:51 → MIA 23:35DL 2187	8h 47m	94%	68%
Southwest Details →	MDW 05:20 → AUS 07:50WN 2726	3h 58m Austin	AUS 11:48 → MIA 15:38WN 362	9h 18m	100%	64%

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.


Southwest WN 2900 MDW 07:50 → STL American AA 3954 STL 11:00 → MIA Connection details →	1h 50m	5h 56m	95%	85%
Delta DL 4688 MDW 13:26 → DTW American AA 3358 DTW 18:57 → MIA Connection details →	3h 13m	7h 44m	93%	84%
Southwest WN 2815 MDW 05:10 → MCO American AA 1712 MCO 11:02 → MIA Connection details →	2h 22m	6h 04m	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