Itineraries flown on 20+ days in the Jun 6 – Jul 31, 2026 schedule · each leg’s record Aug 2025 – Jul 2026

The best bet has a stop: Southwest via Midway (5h 28m) reaches Boston on time 4 times in 5, against 69% on the nonstop.

Nonstops (seasonal or thin)


Southwest	DAL	BOS	3h 40m	70%	0.8%	260	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

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


Southwest + Unitedtwo ticketsDetails →	DAL 19:10 → DEN 20:30WN 1304	3h 29m Denver	DEN 23:59 → BOS 05:58 +1UA 2656	9h 48m	98%	89%
Southwest + Unitedtwo ticketsDetails →	DAL 06:00 → DEN 07:00WN 1296	2h 40m Denver	DEN 09:40 → BOS 15:44UA 1232	8h 44m	100%	85%
Southwest + Deltatwo ticketsDetails →	DAL 06:00 → ATL 09:05WN 1261	2h 05m Atlanta	ATL 11:10 → BOS 13:47DL 862	6h 47m	98%	82%
Southwest + Deltatwo ticketsDetails →	DAL 06:10 → DCA 10:00WN 3351	2h 55m Washington	DCA 12:55 → BOS 14:39DL 5592 · flown by Republic	7h 29m	100%	81%
Southwest Details →	DAL 06:00 → MDW 08:15WN 1355	55m Chicago	MDW 09:10 → BOS 12:28WN 1405	5h 28m	88%	80%
Southwest + Deltatwo ticketsDetails →	DAL 06:05 → MCI 07:35WN 4631	2h 05m Kansas City	MCI 09:40 → BOS 13:49DL 675	6h 50m	95%	80%
Southwest + Americantwo ticketsDetails →	DAL 06:00 → PHX 06:28WN 1379	2h 14m Phoenix	PHX 08:42 → BOS 16:55AA 1564	9h 55m	100%	78%
Southwest + Deltatwo ticketsDetails →	DAL 06:05 → MCO 09:45WN 1434	1h 35m Orlando	MCO 11:20 → BOS 14:24DL 1580	7h 19m	94%	76%
Tight connection: often missed
Delta Details →	DAL 18:40 → ATL 22:00DL 2780	50m Atlanta	ATL 22:50 → BOS 01:31 +1DL 865	5h 51m	72%	54%
Southwest Details →	DAL 15:10 → BWI 19:10WN 1283	55m Baltimore	BWI 20:05 → BOS 21:40WN 4361	5h 30m	60%	20%
Southwest Details →	DAL 17:55 → BNA 19:45WN 277	50m Nashville	BNA 20:35 → BOS 00:55 +1WN 459	5h 15m	23%	10%

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

MDW · 55m · leaves 06:00 12%

BNA · 1h 20m · leaves 07:05 14%

Afternoon and evening

ATL · 50m · leaves 18:40 28%

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