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 CHS → MDW flights land within a few points of 82% on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	CHS	MDW	2h 15m	82%	0.5%	370	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 Charleston). Layovers up to 4 hours. Pick a connection for the details.


American + Southwesttwo ticketsDetails →	CHS 06:41 → CLT 07:47AA 3235	3h 48m Charlotte	CLT 11:35 → MDW 12:35WN 4529	6h 54m	99%	95%
Southwest Details →	CHS 06:30 → BNA 06:55WN 1141	2h 25m Nashville	BNA 09:20 → MDW 11:00WN 1473	5h 30m	100%	88%
Delta + Southwesttwo ticketsDetails →	CHS 05:10 → ATL 06:21DL 3055	3h 39m Atlanta	ATL 10:00 → MDW 11:00WN 224	6h 50m	100%	87%
Delta Details →	CHS 07:20 → ATL 08:34DL 1664	2h 31m Atlanta	ATL 11:05 → MDW 12:05DL 2417	5h 45m	98%	84%
American + Southwesttwo ticketsDetails →	CHS 05:00 → CLT 06:01AA 3298	1h 34m Charlotte	CLT 07:35 → MDW 08:40WN 3048	4h 40m	95%	83%
American + Southwesttwo ticketsDetails →	CHS 06:00 → DCA 07:35AA 3089	1h 50m Washington	DCA 09:25 → MDW 10:20WN 1444	5h 20m	97%	82%
Delta Details →	CHS 06:15 → ATL 07:25DL 2124	1h 44m Atlanta	ATL 09:09 → MDW 10:09DL 1063	4h 54m	96%	81%
American + Southwesttwo ticketsDetails →	CHS 06:06 → PHL 08:00AA 5067 · flown by PSA	3h 22m Philadelphia	PHL 11:22 → MDW 12:32WN 3224	7h 26m	96%	78%
Tight connection: often missed
Southwest Details →	CHS 16:10 → BWI 17:45WN 470	1h 15m Baltimore	BWI 19:00 → MDW 20:05WN 1005	4h 55m	66%	41%
Southwest Details →	CHS 17:40 → DEN 19:25WN 1145	1h 25m Denver	DEN 20:50 → MDW 00:15 +1WN 1615	7h 32m	65%	23%

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