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, any airlines

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.


American + Southwesttwo ticketsDetails →	IND 06:32 → CLT 08:15AA 2938	3h 20m Charlotte	CLT 11:35 → MDW 12:35WN 4529	7h 03m	98%	94%
Delta + Southwesttwo ticketsDetails →	IND 06:00 → ATL 07:39DL 3105	2h 21m Atlanta	ATL 10:00 → MDW 11:00WN 224	6h 00m	98%	86%
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%
American + Southwesttwo ticketsDetails →	IND 06:45 → PHL 08:41AA 4613 · flown by Republic	2h 41m Philadelphia	PHL 11:22 → MDW 12:32WN 3224	6h 47m	99%	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 + Southwesttwo ticketsDetails →	IND 06:10 → LGA 08:17DL 5771 · flown by Republic	2h 38m New York	LGA 10:55 → MDW 12:15WN 4573	7h 05m	100%	82%
American + Southwesttwo ticketsDetails →	IND 07:39 → DCA 09:30AA 4352 · flown by Republic	2h 30m Washington	DCA 12:00 → MDW 13:00WN 1445	6h 21m	95%	79%
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.

The table above includes two-ticket connections (marked “two tickets”), held to the 90-minute minimum. One ticket only →

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