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, 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 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 Details →	CLT 05:30 → ATL 06:42DL 3186	2h 27m Atlanta	ATL 09:09 → MDW 10:09DL 1063	5h 39m	99%	80%
Delta Details →	CLT 12:19 → ATL 13:41DL 3190	1h 34m Atlanta	ATL 15:15 → MDW 16:15DL 1728	4h 56m	96%	72%
Delta Details →	CLT 09:42 → DTW 11:30DL 1639	55m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	4h 04m	88%	71%
Delta Details →	CLT 16:56 → ATL 18:15DL 3032	3h 00m Atlanta	ATL 21:15 → MDW 22:17DL 1076	6h 21m	92%	70%
Delta Details →	CLT 06:00 → DTW 07:45DL 1405	1h 05m Detroit	DTW 08:50 → MDW 09:14DL 4684 · flown by Endeavor	4h 14m	95%	69%
Southwest Details →	CLT 07:50 → BWI 09:20WN 4695	3h 10m Baltimore	BWI 12:30 → MDW 13:30WN 435	6h 40m	98%	68%

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.


Delta DL 3186 CLT 05:30 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	3h 18m	6h 30m	99%	84%
American AA 2727 CLT 05:45 → PHL Southwest WN 3224 PHL 11:22 → MDW Connection details →	3h 55m	7h 47m	97%	83%
American AA 5144 CLT 07:10 → CMH Southwest WN 4386 CMH 11:55 → MDW Connection details →	3h 09m	6h 00m	97%	82%

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