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 70-minute layover misses 6% of the time at 9 am and 42% of the time at 7 pm.

Nonstops (seasonal or thin)


Delta	MKE	BOS	2h 25m	73%	4.0%	568	Flying now
JetBlue	MKE	BOS	2h 22m	70%	0.0%	172	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 Milwaukee). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	MKE 05:45 → MDW 06:35WN 3178	2h 35m Chicago	MDW 09:10 → BOS 12:28WN 1405	5h 43m	100%	92%
American Details →	MKE 05:02 → ORD 06:14AA 6358 · flown by SkyWest	2h 16m Chicago	ORD 08:30 → BOS 12:07AA 4106 · flown by Envoy	6h 05m	96%	86%
United Details →	MKE 05:00 → ORD 05:59UA 5799 · flown by SkyWest	1h 34m Chicago	ORD 07:33 → BOS 11:05UA 1076	5h 05m	91%	84%
American Details →	MKE 07:01 → CLT 10:07AA 2866	1h 11m Charlotte	CLT 11:18 → BOS 13:33AA 1611	5h 32m	91%	81%
United Details →	MKE 06:20 → ORD 07:30UA 5896 · flown by SkyWest	1h 45m Chicago	ORD 09:15 → BOS 12:57UA 1117	5h 37m	96%	81%
Delta Details →	MKE 05:40 → ATL 08:42DL 1221	1h 18m Atlanta	ATL 10:00 → BOS 12:44DL 855	6h 04m	94%	80%
Delta Details →	MKE 06:20 → MSP 07:43DL 4460 · flown by SkyWest	2h 22m Minneapolis	MSP 10:05 → BOS 13:51DL 2655	6h 35m	96%	78%
United Details →	MKE 06:14 → EWR 09:35UA 3470 · flown by Republic	2h 24m Newark	EWR 11:59 → BOS 13:16UA 1669	6h 02m	95%	77%
Tight connection: often missed
Delta Details →	MKE 18:40 → ATL 21:52DL 1206	58m Atlanta	ATL 22:50 → BOS 01:31 +1DL 865	5h 51m	70%	54%
Delta Details →	MKE 10:50 → LGA 14:09DL 5623 · flown by Republic	51m New York	LGA 15:00 → BOS 16:31DL 5727 · flown by Republic	4h 41m	73%	40%
American Details →	MKE 12:49 → DCA 15:59AA 5286 · flown by PSA	1h 01m Washington	DCA 17:00 → BOS 18:47AA 3207	4h 58m	61%	24%

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 · 1h 05m · leaves 05:45 2%

BNA · 1h 00m · leaves 07:40 5%

ATL · 1h 18m · leaves 05:40 6%

Afternoon and evening

DCA · 1h 01m · leaves 12:49 39%

DTW · 53m · leaves 18:49 42%

ORD · 1h 05m · leaves 17:29 42%

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 6358 MKE 05:02 → ORD United UA 1117 ORD 09:15 → BOS Connection details →	3h 01m	6h 55m	96%	82%
United UA 5799 MKE 05:00 → ORD American AA 4106 ORD 08:30 → BOS Connection details →	2h 31m	6h 07m	92%	81%
American AA 4914 MKE 06:08 → ORD United UA 1606 ORD 10:25 → BOS Connection details →	2h 55m	6h 54m	96%	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