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, 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 Richmond). Layovers up to 4 hours. Pick a connection for the details.


Delta Details →	RIC 05:45 → ATL 07:20DL 1460	3h 45m Atlanta	ATL 11:05 → MDW 12:05DL 2417	7h 20m	99%	83%
Delta Details →	RIC 10:19 → ATL 12:01DL 1462	3h 14m Atlanta	ATL 15:15 → MDW 16:15DL 1728	6h 56m	99%	72%
Southwest Details →	RIC 06:15 → BWI 07:10WN 3438	2h 25m Baltimore	BWI 09:35 → MDW 10:35WN 4217	5h 20m	100%	66%
Delta Details →	RIC 17:40 → ATL 19:30DL 1214	1h 45m Atlanta	ATL 21:15 → MDW 22:17DL 1076	5h 37m	89%	65%
Delta Details →	RIC 06:00 → DTW 07:55DL 5453 · flown by Endeavor	55m Detroit	DTW 08:50 → MDW 09:14DL 4684 · flown by Endeavor	4h 14m	83%	61%
Delta Details →	RIC 12:36 → DTW 14:21DL 3166	3h 46m Detroit	DTW 18:07 → MDW 18:25DL 4677 · flown by Endeavor	6h 53m	100%	59%
Delta Details →	RIC 06:35 → MSP 08:40DL 5344 · flown by Endeavor	2h 50m Minneapolis	MSP 11:30 → MDW 13:09DL 4820 · flown by Endeavor	7h 34m	96%	57%
Southwest Details →	RIC 16:45 → DEN 18:30WN 2557	2h 20m Denver	DEN 20:50 → MDW 00:15 +1WN 1615	8h 27m	86%	30%
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.


American AA 1063 RIC 06:30 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	3h 41m	7h 05m	98%	92%
American AA 5973 RIC 06:26 → PHL Southwest WN 3224 PHL 11:22 → MDW Connection details →	3h 42m	7h 06m	100%	85%
Delta DL 1460 RIC 05:45 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	2h 40m	6h 15m	97%	84%

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