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

No clear winner: airlines and hours on this route all land within a few points of 77% on time.

Nonstops


Southwest	MDW	MCO	2h 35m	76%	1.5%	2,543	Flying now
Frontier	MDW	MCO	2h 48m	82%	1.9%	213	Not flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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


Southwest Details →	MDW 06:50 → DEN 08:20WN 2765	1h 40m Denver	DEN 10:00 → MCO 15:55WN 1339	8h 05m	100%	85%
Southwest Details →	MDW 08:00 → MCI 09:30WN 2808	2h 15m Kansas City	MCI 11:45 → MCO 15:35WN 3238	6h 35m	100%	84%
Southwest Details →	MDW 07:52 → BUF 10:25WN 758	2h 15m Buffalo	BUF 12:40 → MCO 15:15WN 762	6h 23m	100%	81%
Southwest Details →	MDW 06:40 → HOU 09:15WN 4497	2h 07m Houston	HOU 11:22 → MCO 14:52WN 2034	7h 12m	100%	79%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	1h 30m Atlanta	ATL 10:25 → MCO 12:00DL 664	5h 00m	94%	76%
Southwest Details →	MDW 05:00 → DAL 07:15WN 1377	1h 55m Dallas	DAL 09:10 → MCO 12:50WN 1725	6h 50m	100%	76%
Southwest Details →	MDW 05:20 → AUS 07:50WN 2726	2h 25m Austin	AUS 10:15 → MCO 13:55WN 349	7h 35m	100%	76%
Southwest Details →	MDW 07:40 → MHT 10:50WN 830	1h 40m Manchester	MHT 12:30 → MCO 15:35WN 2919	6h 55m	100%	76%
Tight connection: often missed
Delta Details →	MDW 17:10 → ATL 20:22DL 1728	58m Atlanta	ATL 21:20 → MCO 22:56DL 1733	4h 46m	74%	47%
Southwest Details →	MDW 18:00 → STL 19:10WN 2904	50m St Louis	STL 20:00 → MCO 23:30WN 3950	4h 30m	57%	34%
Southwest Details →	MDW 20:35 → PHX 22:15WN 2863	50m Phoenix	PHX 23:05 → MCO 06:20 +1WN 4508	8h 45m	30%	22%

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

BWI · 1h 03m · leaves 08:55 7%

MSP · 1h 10m · leaves 09:54 11%

Afternoon and evening

DEN · 50m · leaves 21:25 51%

ROC · 50m · leaves 13:20 59%

PHX · 50m · leaves 20:35 70%

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 4088 MDW 07:55 → CLE United UA 1488 CLE 12:16 → MCO Connection details →	2h 06m	5h 48m	95%	88%
Southwest WN 4976 MDW 06:00 → DCA American AA 2062 DCA 11:25 → MCO Connection details →	2h 40m	6h 51m	100%	85%
Southwest WN 2726 MDW 05:20 → AUS Frontier F9 4524 AUS 10:42 → MCO Connection details →	2h 52m	8h 13m	100%	79%

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