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

No clear winner: Southwest’s MDW → IND flights land within a few points of 83% on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	MDW	IND	1h 05m	83%	1.4%	732	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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


Delta Details →	MDW 09:17 → DTW 11:35DL 4674 · flown by Endeavor	2h 25m Detroit	DTW 14:00 → IND 15:19DL 5846 · flown by Republic	5h 02m	96%	87%
Southwest Details →	MDW 05:10 → MCO 08:40WN 2815	1h 10m Orlando	MCO 09:50 → IND 12:12WN 4655	6h 02m	93%	87%
Southwest Details →	MDW 05:15 → DEN 06:50WN 2989	1h 50m Denver	DEN 08:40 → IND 13:00WN 1552	6h 45m	100%	86%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 10m Atlanta	ATL 11:05 → IND 12:40DL 3013	5h 40m	95%	82%
Southwest Details →	MDW 10:20 → MCI 11:45WN 2529	1h 45m Kansas City	MCI 13:30 → IND 16:00WN 1432	4h 40m	100%	81%
Southwest Details →	MDW 07:00 → BWI 09:45WN 2742	1h 00m Baltimore	BWI 10:45 → IND 12:30WN 960	4h 30m	91%	78%
Delta Details →	MDW 09:54 → MSP 11:35DL 5469 · flown by Endeavor	1h 20m Minneapolis	MSP 12:55 → IND 15:33DL 2910	4h 39m	93%	77%
Southwest Details →	MDW 06:30 → MCO 10:05WN 2816	1h 10m Orlando	MCO 11:15 → IND 13:40WN 4721	6h 10m	93%	77%
Tight connection: often missed
Southwest Details →	MDW 11:50 → AUS 14:25WN 2728	55m Austin	AUS 15:20 → IND 18:45WN 927	5h 55m	54%	43%
Delta Details →	MDW 19:06 → MSP 20:51DL 4713 · flown by Endeavor	49m Minneapolis	MSP 21:40 → IND 00:17 +1DL 674	4h 11m	52%	40%

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

MCO · 1h 10m · leaves 06:30 7%

MSP · 1h 20m · leaves 09:54 7%

DTW · 47m · leaves 09:17 21%

Afternoon and evening

DAL · 1h 20m · leaves 16:20 22%

MSP · 49m · leaves 19:06 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.


Southwest WN 4976 MDW 06:00 → DCA American AA 4407 DCA 11:59 → IND Connection details →	3h 14m	6h 56m	100%	95%
Southwest WN 1775 MDW 07:55 → DTW Delta DL 5846 DTW 14:00 → IND Connection details →	3h 55m	6h 24m	100%	91%
Southwest WN 2869 MDW 10:15 → MSP Delta DL 1456 MSP 15:45 → IND Connection details →	4h 00m	7h 07m	98%	87%

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