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 → BDL flights land within a few points of 77% on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	MDW	BDL	2h 02m	77%	1.6%	823	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

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


Southwest + JetBluetwo ticketsDetails →	MDW 06:30 → MCO 10:05WN 2816	2h 40m Orlando	MCO 12:45 → BDL 15:40B6 2938	8h 10m	98%	91%
Delta Details →	MDW 09:17 → DTW 11:35DL 4674 · flown by Endeavor	2h 52m Detroit	DTW 14:27 → BDL 16:13DL 2814	5h 56m	98%	83%
Southwest + Americantwo ticketsDetails →	MDW 07:40 → PHL 10:42WN 4122	2h 09m Philadelphia	PHL 12:51 → BDL 14:11AA 6035 · flown by Piedmont	5h 31m	98%	82%
Southwest + Deltatwo ticketsDetails →	MDW 07:15 → ATL 10:05WN 3054	3h 49m Atlanta	ATL 13:54 → BDL 16:14DL 2739	7h 59m	100%	79%
Southwest Details →	MDW 07:00 → BWI 09:45WN 2742	3h 05m Baltimore	BWI 12:50 → BDL 14:10WN 1143	6h 10m	100%	79%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	1h 30m Atlanta	ATL 10:25 → BDL 12:45DL 1082	5h 44m	94%	78%
Delta Details →	MDW 09:54 → MSP 11:35DL 5469 · flown by Endeavor	2h 51m Minneapolis	MSP 14:26 → BDL 18:04DL 2285	7h 10m	98%	77%
Southwest + Deltatwo ticketsDetails →	MDW 08:55 → ATL 11:45WN 4154	3h 54m Atlanta	ATL 15:39 → BDL 18:04DL 2735	8h 09m	100%	75%
Tight connection: often missed
Southwest Details →	MDW 19:00 → BWI 21:55WN 2745	1h 00m Baltimore	BWI 22:55 → BDL 00:20 +1WN 1879	4h 17m	66%	41%

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

BWI · 1h 05m · leaves 08:55 5%

Afternoon and evening

ATL · 1h 14m · leaves 17:10 20%

BWI · 1h 00m · leaves 19:00 34%

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