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 IND → MDW (1h 05m) reaches Chicago on time 78% of the time; the most reliable connection, Delta via Detroit (3h 34m), 65%.

Nonstops (seasonal or thin)


Southwest	IND	MDW	1h 05m	78%	1.2%	733	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 Indianapolis). Layovers up to 4 hours. Pick a connection for the details.


Delta Details →	IND 08:05 → ATL 09:44DL 1901	1h 21m Atlanta	ATL 11:05 → MDW 12:05DL 2417	5h 00m	98%	84%
Southwest Details →	IND 05:20 → HOU 06:45WN 4645	1h 25m Houston	HOU 08:10 → MDW 10:40WN 1294	6h 20m	100%	84%
Southwest Details →	IND 07:00 → BNA 07:10WN 2111	2h 10m Nashville	BNA 09:20 → MDW 11:00WN 1473	5h 00m	96%	83%
Delta Details →	IND 06:00 → ATL 07:39DL 3105	1h 30m Atlanta	ATL 09:09 → MDW 10:09DL 1063	5h 09m	97%	82%
Delta Details →	IND 07:47 → DTW 09:03DL 4897 · flown by Endeavor	3h 22m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	5h 59m	97%	77%
Southwest Details →	IND 05:10 → MCO 07:25WN 2129	1h 45m Orlando	MCO 09:10 → MDW 10:55WN 4037	6h 45m	100%	77%
Southwest Details →	IND 06:35 → DAL 07:45WN 3012	2h 20m Dallas	DAL 10:05 → MDW 12:20WN 1357	6h 45m	96%	74%
Delta Details →	IND 11:23 → ATL 13:00DL 2952	2h 15m Atlanta	ATL 15:15 → MDW 16:15DL 1728	5h 52m	99%	73%
Tight connection: often missed
Southwest Details →	IND 19:25 → TPA 21:40WN 2140	50m Tampa	TPA 22:30 → MDW 00:10 +1WN 4035	5h 45m	53%	36%
Southwest Details →	IND 15:55 → DEN 16:38WN 4826	57m Denver	DEN 17:35 → MDW 21:00WN 1604	6h 05m	71%	19%
Southwest Details →	IND 20:25 → DAL 21:35WN 198	47m Dallas	DAL 22:22 → MDW 01:00 +1WN 1359	5h 12m	35%	11%

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

DTW · 55m · leaves 06:40 9%

MCO · 50m · leaves 05:10 14%

Afternoon and evening

RSW · 1h 05m · leaves 13:40 20%

ATL · 49m · leaves 18:40 23%

DEN · 57m · leaves 15:55 29%

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 2938 IND 06:32 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	3h 20m	7h 03m	98%	94%
Delta DL 3105 IND 06:00 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	2h 21m	6h 00m	98%	86%
American AA 4613 IND 06:45 → PHL Southwest WN 3224 PHL 11:22 → MDW Connection details →	2h 41m	6h 47m	99%	84%

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