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

No clear winner: airlines and hours on this route all land within a few points of 3 in 4 on time.

Nonstops (seasonal or thin)


American	MSN	BOS	2h 33m	89%	2.2%	45	Flying now
Delta	MSN	BOS	2h 36m	62%	3.6%	55	Flying now

Best connections, one ticket

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


American Details →	MSN 05:00 → ORD 06:15AA 4322 · flown by Envoy	2h 15m Chicago	ORD 08:30 → BOS 12:07AA 4106 · flown by Envoy	6h 07m	96%	88%
United Details →	MSN 05:00 → DEN 06:42UA 5545 · flown by SkyWest	1h 03m Denver	DEN 07:45 → BOS 13:49UA 558	7h 49m	97%	87%
United Details →	MSN 05:00 → ORD 06:17UA 4707 · flown by SkyWest	1h 16m Chicago	ORD 07:33 → BOS 11:05UA 1076	5h 05m	93%	85%
United Details →	MSN 06:41 → ORD 07:54UA 5902 · flown by SkyWest	1h 21m Chicago	ORD 09:15 → BOS 12:57UA 1117	5h 16m	98%	83%
American Details →	MSN 07:00 → CLT 10:16AA 1002	1h 02m Charlotte	CLT 11:18 → BOS 13:33AA 1611	5h 33m	93%	83%
Delta Details →	MSN 05:48 → ATL 09:00DL 1160	1h 00m Atlanta	ATL 10:00 → BOS 12:44DL 855	5h 56m	93%	78%
Delta Details →	MSN 06:00 → MSP 07:09DL 1274	2h 56m Minneapolis	MSP 10:05 → BOS 13:51DL 2655	6h 55m	97%	77%
United Details →	MSN 06:29 → EWR 09:50UA 3482 · flown by Republic	2h 09m Newark	EWR 11:59 → BOS 13:16UA 1669	5h 47m	96%	76%
Tight connection: often missed
Delta Details →	MSN 18:32 → DTW 20:58DL 5214 · flown by Endeavor	55m Detroit	DTW 21:53 → BOS 23:54DL 1187	4h 22m	72%	50%
United Details →	MSN 15:18 → DEN 16:45UA 2338	55m Denver	DEN 17:40 → BOS 23:44UA 1356	7h 26m	68%	48%
Delta Details →	MSN 15:10 → LGA 18:29DL 5033 · flown by Endeavor	1h 31m New York	LGA 20:00 → BOS 21:31DL 5850 · flown by Republic	5h 21m	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

DEN · 1h 03m · leaves 05:00 3%

CLT · 1h 02m · leaves 07:00 7%

ATL · 1h 00m · leaves 05:48 7%

Afternoon and evening

DEN · 55m · leaves 15:18 32%

PHL · 57m · leaves 13:17 37%

DCA · 51m · leaves 16:34 58%

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 4322 MSN 05:00 → ORD United UA 1117 ORD 09:15 → BOS Connection details →	3h 00m	6h 57m	96%	84%
United UA 4707 MSN 05:00 → ORD American AA 4106 ORD 08:30 → BOS Connection details →	2h 13m	6h 07m	93%	82%
American AA 4688 MSN 06:34 → ORD United UA 1606 ORD 10:25 → BOS Connection details →	2h 25m	6h 28m	93%	75%

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