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 → RIC flights land within a few points of 73% on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	MDW	RIC	1h 50m	73%	1.0%	413	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

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


Southwest + Deltatwo ticketsDetails →	MDW 07:15 → ATL 10:05WN 3054	2h 25m Atlanta	ATL 12:30 → RIC 14:05DL 1437	5h 50m	100%	88%
Southwest + Americantwo ticketsDetails →	MDW 07:40 → PHL 10:42WN 4122	2h 30m Philadelphia	PHL 13:12 → RIC 14:35AA 5843 · flown by Piedmont	5h 55m	98%	87%
Southwest + Americantwo ticketsDetails →	MDW 05:15 → LGA 08:15WN 2801	3h 01m New York	LGA 11:16 → RIC 12:50AA 4501 · flown by Republic	6h 32m	100%	83%
Southwest + Deltatwo ticketsDetails →	MDW 08:55 → ATL 11:45WN 4154	4h 00m Atlanta	ATL 15:45 → RIC 17:26DL 3152	7h 31m	100%	82%
Southwest + JetBluetwo ticketsDetails →	MDW 05:10 → MCO 08:40WN 2815	2h 05m Orlando	MCO 10:45 → RIC 12:50B6 670	6h 40m	95%	79%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	1h 20m Atlanta	ATL 10:15 → RIC 11:56DL 2650	4h 56m	92%	78%
Southwest + Deltatwo ticketsDetails →	MDW 09:10 → BOS 12:28WN 1405	3h 42m Boston	BOS 16:10 → RIC 18:17DL 5665 · flown by Republic	8h 11m	100%	76%
Delta Details →	MDW 09:17 → DTW 11:35DL 4674 · flown by Endeavor	3h 00m Detroit	DTW 14:35 → RIC 16:21DL 4096 · flown by SkyWest	6h 04m	98%	73%
Tight connection: often missed
Southwest Details →	MDW 11:20 → BNA 12:45WN 2733	1h 05m Nashville	BNA 13:50 → RIC 16:30WN 4530	4h 10m	60%	19%

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 06:00 8%

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