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

No clear winner: Southwest’s MDW → BOS flights land within a few points of 2 in 3 on time whatever the hour.

Nonstops


Southwest	MDW	BOS	2h 15m	68%	1.2%	1,360	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 Chicago). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	MDW 06:50 → DEN 08:20WN 2765	1h 40m Denver	DEN 10:00 → BOS 16:05WN 3690	8h 15m	100%	83%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 15m Atlanta	ATL 11:10 → BOS 13:47DL 862	6h 47m	95%	77%
Southwest Details →	MDW 07:50 → STL 09:10WN 2900	55m St Louis	STL 10:05 → BOS 13:40WN 3891	4h 50m	93%	76%
Delta Details →	MDW 17:10 → ATL 20:22DL 1728	2h 28m Atlanta	ATL 22:50 → BOS 01:31 +1DL 865	7h 21m	95%	72%
Southwest Details →	MDW 07:00 → BWI 09:45WN 2742	55m Baltimore	BWI 10:40 → BOS 12:10WN 887	4h 10m	84%	67%
Delta Details →	MDW 09:17 → DTW 11:35DL 4674 · flown by Endeavor	2h 26m Detroit	DTW 14:01 → BOS 16:10DL 1171	5h 53m	96%	67%
Southwest Details →	MDW 08:55 → BWI 11:45WN 1355	2h 05m Baltimore	BWI 13:50 → BOS 15:25WN 211	5h 30m	100%	67%
Delta Details →	MDW 09:54 → MSP 11:35DL 5469 · flown by Endeavor	3h 40m Minneapolis	MSP 15:15 → BOS 19:11DL 2591	8h 17m	98%	65%
Tight connection: often missed
Southwest Details →	MDW 16:15 → DEN 18:00WN 2769	1h 05m Denver	DEN 19:05 → BOS 01:00 +1WN 1494	7h 45m	64%	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

STL · 55m · leaves 07:50 7%

ATL · 1h 05m · leaves 06:00 9%

MSP · 1h 11m · leaves 09:54 11%

Afternoon and evening

ATL · 59m · leaves 12:50 15%

DEN · 1h 05m · leaves 16:15 36%

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.


Southwest WN 2801 MDW 05:15 → LGA American AA 4367 LGA 10:30 → BOS Connection details →	2h 15m	5h 38m	98%	83%
Southwest WN 4976 MDW 06:00 → DCA Delta DL 5693 DCA 11:47 → BOS Connection details →	3h 02m	6h 30m	100%	81%
Southwest WN 2815 MDW 05:10 → MCO Delta DL 1580 MCO 11:20 → BOS Connection details →	2h 40m	8h 14m	100%	81%

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