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 MDW → CLT flights land within a few points of 3 in 4 on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	MDW	CLT	1h 50m	76%	1.4%	719	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

Ranked by chance you reach Charlotte on time. Total trip = scheduled departure to arrival, layover included (Charlotte is 1 h ahead of Chicago). Layovers up to 4 hours. Pick a connection for the details.


Southwest + Americantwo ticketsDetails →	MDW 05:00 → TPA 08:25WN 2906	3h 31m Tampa	TPA 11:56 → CLT 13:53AA 2828	7h 53m	100%	89%
Southwest + Americantwo ticketsDetails →	MDW 08:00 → MCI 09:30WN 2808	2h 45m Kansas City	MCI 12:15 → CLT 15:43AA 2052	6h 43m	100%	87%
Southwest + Americantwo ticketsDetails →	MDW 06:30 → MCO 10:05WN 2816	2h 43m Orlando	MCO 12:48 → CLT 14:45AA 2074	7h 15m	98%	87%
Southwest + Deltatwo ticketsDetails →	MDW 07:55 → DTW 10:05WN 1775	4h 00m Detroit	DTW 14:05 → CLT 15:58DL 1429	7h 03m	100%	85%
Southwest + Americantwo ticketsDetails →	MDW 07:40 → BOS 10:55WN 4611	3h 31m Boston	BOS 14:26 → CLT 17:00AA 1611	8h 20m	100%	85%
Southwest + Americantwo ticketsDetails →	MDW 09:10 → PHL 12:10WN 3222	3h 40m Philadelphia	PHL 15:50 → CLT 17:53AA 2573	7h 43m	100%	84%
Southwest + Deltatwo ticketsDetails →	MDW 07:15 → ATL 10:05WN 3054	2h 15m Atlanta	ATL 12:20 → CLT 13:35DL 2157	5h 20m	100%	84%
Southwest + Americantwo ticketsDetails →	MDW 05:15 → LGA 08:15WN 2801	3h 55m New York	LGA 12:10 → CLT 14:14AA 1150	7h 59m	100%	83%

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

ATL · 1h 15m · leaves 06:00 8%

Afternoon and evening

ATL · 1h 12m · leaves 12:50 12%

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