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 14% of the time at 12 pm and 31% of the time at 5 pm.

Nonstops


Southwest	MCO	MDW	2h 50m	71%	1.8%	2,548	Flying now
Frontier	MCO	MDW	3h 00m	76%	1.4%	212	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 Orlando). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	MCO 06:40 → AUS 08:15WN 2594	2h 10m Austin	AUS 10:25 → MDW 12:55WN 4077	7h 15m	100%	88%
Southwest Details →	MCO 06:25 → DEN 08:15WN 2628	1h 45m Denver	DEN 10:00 → MDW 13:25WN 755	8h 00m	100%	87%
Delta Details →	MCO 06:15 → ATL 07:52DL 1494	3h 13m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 50m	99%	85%
Southwest Details →	MCO 06:10 → CMH 08:20WN 2616	3h 35m Columbus	CMH 11:55 → MDW 12:10WN 4386	7h 00m	100%	85%
Southwest Details →	MCO 07:00 → PVD 09:50WN 4545	2h 50m Providence	PVD 12:40 → MDW 14:10WN 3409	8h 10m	100%	83%
Delta Details →	MCO 05:30 → ATL 07:02DL 1548	2h 07m Atlanta	ATL 09:09 → MDW 10:09DL 1063	5h 39m	98%	82%
Southwest Details →	MCO 06:15 → DAL 07:50WN 7	2h 15m Dallas	DAL 10:05 → MDW 12:20WN 1357	7h 05m	100%	81%
Southwest Details →	MCO 11:15 → IND 13:40WN 4721	4h 00m Indianapolis	IND 17:40 → MDW 17:55WN 961	7h 40m	100%	80%
Tight connection: often missed
Southwest Details →	MCO 18:40 → STL 20:20WN 3236	1h 25m St Louis	STL 21:45 → MDW 22:55WN 3957	5h 10m	58%	39%
Southwest Details →	MCO 19:00 → BNA 20:05WN 2607	1h 35m Nashville	BNA 21:40 → MDW 19:10WN 578	5h 10m	62%	26%
Southwest Details →	MCO 12:50 → AUS 14:30WN 4719	1h 00m Austin	AUS 15:30 → MDW 18:00WN 360	6h 10m	72%	12%

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 17m · leaves 06:15 3%

MSY · 1h 20m · leaves 09:35 7%

DTW · 52m · leaves 09:00 14%

Afternoon and evening

DAL · 1h 02m · leaves 19:35 48%

ATL · 53m · leaves 15:22 60%

DEN · 50m · leaves 15:50 62%

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 461 MCO 06:15 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	3h 31m	7h 20m	99%	95%
Delta DL 1548 MCO 05:30 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	2h 58m	6h 30m	98%	85%
American AA 2745 MCO 06:57 → DCA Southwest WN 1445 DCA 12:00 → MDW Connection details →	2h 40m	7h 03m	97%	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