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 RIC → MDW flights land within a few points of 78% on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	RIC	MDW	2h 00m	78%	1.0%	413	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 Richmond). Layovers up to 4 hours. Pick a connection for the details.


American + Southwesttwo ticketsDetails →	RIC 06:30 → CLT 07:54AA 1063	3h 41m Charlotte	CLT 11:35 → MDW 12:35WN 4529	7h 05m	98%	92%
American + Southwesttwo ticketsDetails →	RIC 06:26 → PHL 07:40AA 5973 · flown by Piedmont	3h 42m Philadelphia	PHL 11:22 → MDW 12:32WN 3224	7h 06m	100%	85%
Delta + Southwesttwo ticketsDetails →	RIC 05:45 → ATL 07:20DL 1460	2h 40m Atlanta	ATL 10:00 → MDW 11:00WN 224	6h 15m	97%	84%
Delta Details →	RIC 07:00 → ATL 08:48DL 1402	2h 17m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 05m	97%	82%
American + Southwesttwo ticketsDetails →	RIC 06:07 → LGA 07:29AA 4451 · flown by Republic	3h 26m New York	LGA 10:55 → MDW 12:15WN 4573	7h 08m	96%	79%
Delta + Southwesttwo ticketsDetails →	RIC 08:05 → ATL 09:45DL 1415	2h 45m Atlanta	ATL 12:30 → MDW 13:25WN 225	6h 20m	96%	72%
Delta Details →	RIC 10:19 → ATL 12:01DL 1462	3h 14m Atlanta	ATL 15:15 → MDW 16:15DL 1728	6h 56m	99%	72%
Delta + Southwesttwo ticketsDetails →	RIC 06:35 → MSP 08:40DL 5344 · flown by Endeavor	1h 45m Minneapolis	MSP 10:25 → MDW 11:55WN 4345	6h 20m	88%	70%
Tight connection: often missed
Delta Details →	RIC 18:31 → ATL 20:24DL 3152	51m Atlanta	ATL 21:15 → MDW 22:17DL 1076	4h 46m	74%	55%

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 20m · leaves 08:05 6%

DTW · 55m · leaves 06:00 17%

Afternoon and evening

ATL · 51m · leaves 18:31 26%

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