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

Connect in the morning. The same 75-minute layover misses 5% of the time at 7 am and 1 time in 3 at 9 pm.

Nonstops (seasonal or thin)


Delta	BOS	MSN	2h 55m	85%	0.0%	55	Flying now
American	BOS	MSN	2h 47m	60%	6.5%	46	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

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


American Details →	BOS 06:00 → DCA 07:44AA 2159	3h 06m Washington	DCA 10:50 → MSN 12:13AA 4523 · flown by Republic	7h 13m	100%	93%
United Details →	BOS 06:00 → ORD 07:58UA 1414	2h 37m Chicago	ORD 10:35 → MSN 11:49UA 5843 · flown by SkyWest	6h 49m	100%	88%
American Details →	BOS 05:10 → ORD 07:04AA 3324	3h 48m Chicago	ORD 10:52 → MSN 12:02AA 3437 · flown by Envoy	7h 52m	99%	87%
American Details →	BOS 06:05 → CLT 08:30AA 418	2h 42m Charlotte	CLT 11:12 → MSN 12:37AA 5457 · flown by PSA	7h 29m	99%	86%
Delta Details →	BOS 05:30 → ATL 08:15DL 2242	1h 05m Atlanta	ATL 09:20 → MSN 10:22DL 2681	5h 54m	98%	84%
United + Americantwo ticketsDetails →	BOS 08:15 → ORD 10:12UA 1834	3h 02m Chicago	ORD 13:14 → MSN 14:19AA 3716 · flown by Envoy	7h 07m	99%	81%
Delta Details →	BOS 05:55 → MSP 08:04DL 2303	2h 08m Minneapolis	MSP 10:12 → MSN 11:20DL 4102 · flown by SkyWest	6h 25m	98%	81%
Delta Details →	BOS 07:15 → MSP 09:30DL 1138	3h 25m Minneapolis	MSP 12:55 → MSN 14:05DL 4032 · flown by SkyWest	7h 50m	99%	80%
Tight connection: often missed
American Details →	BOS 11:52 → DCA 13:44AA 4349 · flown by Republic	51m Washington	DCA 14:35 → MSN 16:04AA 5599 · flown by PSA	5h 05m	75%	42%
American Details →	BOS 17:05 → PHL 18:49AA 3309	1h 15m Philadelphia	PHL 20:04 → MSN 21:41AA 5512 · flown by PSA	5h 34m	69%	38%
American Details →	BOS 16:06 → DFW 19:38AA 1595	58m Dallas-Fort Worth	DFW 20:36 → MSN 22:53AA 876	7h 47m	73%	33%

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 05m · leaves 05:30 2%

EWR · 1h 09m · leaves 06:05 5%

DCA · 49m · leaves 08:19 11%

Afternoon and evening

DTW · 58m · leaves 17:15 32%

ORD · 1h 05m · leaves 18:31 36%

DEN · 49m · leaves 16:57 38%

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