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 50-minute layover misses 6% of the time at 7 am and 44% of the time at 8 pm.

Nonstops


United	BOS	ORD	2h 58m	77%	2.0%	2,733	Flying now
American	BOS	ORD	3h 10m	74%	3.5%	3,160	Flying now
JetBlue	BOS	ORD	3h 05m	71%	2.8%	544	Flying now
Delta	BOS	ORD	3h 03m	67%	4.3%	1,313	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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


United Details →	BOS 05:45 → IAD 07:23UA 1734	3h 08m Dulles	IAD 10:31 → ORD 11:53UA 1252	7h 08m	100%	89%
American Details →	BOS 06:05 → CLT 08:30AA 418	2h 31m Charlotte	CLT 11:01 → ORD 12:19AA 2908	7h 14m	98%	87%
Delta Details →	BOS 05:30 → DTW 07:39DL 1019	2h 36m Detroit	DTW 10:15 → ORD 10:50DL 3673 · flown by SkyWest	6h 20m	98%	86%
American Details →	BOS 08:36 → SYR 10:06AA 4635 · flown by Republic	53m Syracuse	SYR 10:59 → ORD 12:13AA 4044 · flown by Envoy	4h 37m	91%	84%
American Details →	BOS 07:00 → IND 09:45AA 4435 · flown by Republic	2h 35m Indianapolis	IND 12:20 → ORD 12:48AA 851	6h 48m	99%	83%
American Details →	BOS 06:01 → JFK 07:30AA 4401 · flown by Republic	2h 41m New York	JFK 10:11 → ORD 12:05AA 4365 · flown by Republic	7h 04m	100%	83%
American Details →	BOS 06:00 → DCA 07:44AA 2159	3h 51m Washington	DCA 11:35 → ORD 12:53AA 489	7h 53m	100%	79%
American Details →	BOS 06:00 → PHL 07:37AA 1146	2h 58m Philadelphia	PHL 10:35 → ORD 12:09AA 1041	7h 09m	99%	79%
Tight connection: often missed
American Details →	BOS 11:20 → CLT 13:45AA 3161	50m Charlotte	CLT 14:35 → ORD 15:56AA 2080	5h 36m	75%	53%
American Details →	BOS 17:11 → STL 19:21AA 4678 · flown by Republic	53m St Louis	STL 20:14 → ORD 21:45AA 4144 · flown by Envoy	5h 40m	53%	27%
Delta Details →	BOS 17:05 → JFK 18:43DL 5814 · flown by Republic	52m New York	JFK 19:35 → ORD 21:48DL 5640 · flown by Republic	5h 43m	56%	27%

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

IAH · 1h 20m · leaves 07:25 2%

DCA · 1h 13m · leaves 07:00 3%

CLT · 1h 12m · leaves 06:05 3%

Afternoon and evening

DFW · 52m · leaves 17:57 55%

DCA · 52m · leaves 17:23 56%

EWR · 1h 04m · leaves 17:44 57%

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.


Delta DL 1019 BOS 05:30 → DTW American AA 4103 DTW 10:33 → ORD Connection details →	2h 54m	6h 38m	98%	90%
Southwest WN 752 BOS 05:50 → STL United UA 4517 STL 10:20 → ORD Connection details →	2h 35m	7h 02m	100%	89%
American AA 2159 BOS 06:00 → DCA United UA 2201 DCA 10:30 → ORD Connection details →	2h 46m	6h 48m	99%	87%

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