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 DCA → MDW flights land within a few points of 78% on time whatever the hour.

Nonstops


Southwest	DCA	MDW	2h 05m	78%	2.7%	2,099	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 Washington). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	DCA 06:55 → ATL 08:50WN 4969	1h 10m Atlanta	ATL 10:00 → MDW 11:00WN 224	5h 05m	97%	86%
Southwest Details →	DCA 06:10 → BNA 07:00WN 1425	2h 20m Nashville	BNA 09:20 → MDW 11:00WN 1473	5h 50m	98%	84%
Delta Details →	DCA 06:00 → ATL 07:48DL 410	3h 17m Atlanta	ATL 11:05 → MDW 12:05DL 2417	7h 05m	99%	83%
Southwest Details →	DCA 06:00 → MCI 07:40WN 358	3h 58m Kansas City	MCI 11:38 → MDW 13:02WN 2571	8h 03m	100%	80%
Southwest Details →	DCA 06:10 → DAL 08:10WN 1268	1h 55m Dallas	DAL 10:05 → MDW 12:20WN 1357	7h 10m	98%	77%
Southwest Details →	DCA 06:55 → TPA 09:20WN 2739	1h 25m Tampa	TPA 10:45 → MDW 12:25WN 4033	6h 30m	98%	75%
Delta Details →	DCA 10:16 → ATL 12:08DL 926	3h 07m Atlanta	ATL 15:15 → MDW 16:15DL 1728	6h 59m	99%	71%
Delta Details →	DCA 16:00 → ATL 17:57DL 360	3h 18m Atlanta	ATL 21:15 → MDW 22:17DL 1076	7h 17m	95%	71%
Tight connection: often missed
Southwest Details →	DCA 17:25 → AUS 19:50WN 2593	1h 10m Austin	AUS 21:00 → MDW 23:35WN 361	7h 07m	35%	22%
Southwest Details →	DCA 19:30 → BNA 20:30WN 1428	1h 10m Nashville	BNA 21:40 → MDW 19:10WN 578	4h 40m	54%	18%
Southwest Details →	DCA 12:48 → HOU 14:58WN 1433	1h 00m Houston	HOU 15:58 → MDW 18:22WN 2042	6h 35m	47%	16%

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

DTW · 1h 20m · leaves 06:00 5%

ATL · 1h 13m · leaves 08:00 10%

MCO · 50m · leaves 06:00 15%

Afternoon and evening

BNA · 1h 10m · leaves 19:30 46%

AUS · 1h 10m · leaves 17:25 65%

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 1581 DCA 06:18 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	3h 38m	7h 17m	96%	90%
Delta DL 5608 DCA 08:15 → OMA Southwest WN 4470 OMA 13:10 → MDW Connection details →	2h 57m	7h 20m	97%	87%
Delta DL 410 DCA 06:00 → ATL Southwest WN 224 ATL 10:00 → MDW Connection details →	2h 12m	6h 00m	97%	84%

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