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 CLT → MDW flights land within a few points of 77% on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	CLT	MDW	2h 05m	77%	1.9%	719	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 Charlotte). Layovers up to 4 hours. Pick a connection for the details.


Delta Details →	CLT 06:59 → ATL 08:13DL 2275	2h 52m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 06m	100%	86%
Southwest Details →	CLT 06:35 → BNA 07:00WN 1167	2h 20m Nashville	BNA 09:20 → MDW 11:00WN 1473	5h 25m	98%	86%
Delta + Southwesttwo ticketsDetails →	CLT 05:30 → ATL 06:42DL 3186	3h 18m Atlanta	ATL 10:00 → MDW 11:00WN 224	6h 30m	99%	84%
American + Southwesttwo ticketsDetails →	CLT 05:45 → PHL 07:27AA 2727	3h 55m Philadelphia	PHL 11:22 → MDW 12:32WN 3224	7h 47m	97%	83%
American + Southwesttwo ticketsDetails →	CLT 07:10 → CMH 08:46AA 5144 · flown by PSA	3h 09m Columbus	CMH 11:55 → MDW 12:10WN 4386	6h 00m	97%	82%
American + Deltatwo ticketsDetails →	CLT 07:28 → DTW 09:17AA 1791	3h 08m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	6h 18m	98%	80%
American + Southwesttwo ticketsDetails →	CLT 08:00 → DCA 09:29AA 1977	2h 31m Washington	DCA 12:00 → MDW 13:00WN 1445	6h 00m	97%	79%
American + Southwesttwo ticketsDetails →	CLT 07:30 → BDL 09:28AA 1449	3h 12m Hartford	BDL 12:40 → MDW 14:05WN 427	7h 35m	100%	78%

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 · 1h 05m · leaves 06:00 5%

ATL · 56m · leaves 06:59 16%

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