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 one-hour layover misses 7% of the time at 7 am and 27% of the time at 6 pm.

Nonstops


Southwest	DAL	MDW	2h 10m	71%	2.0%	2,179	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. Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	DAL 06:00 → DEN 07:00WN 1296	3h 00m Denver	DEN 10:00 → MDW 13:25WN 755	7h 25m	100%	87%
Southwest Details →	DAL 07:35 → AUS 08:40WN 1265	1h 45m Austin	AUS 10:25 → MDW 12:55WN 4077	5h 20m	95%	84%
Southwest Details →	DAL 06:10 → DCA 10:00WN 3351	2h 00m Washington	DCA 12:00 → MDW 13:00WN 1445	6h 50m	98%	83%
Southwest Details →	DAL 13:55 → SDF 16:55WN 910	3h 10m Louisville	SDF 20:05 → MDW 20:20WN 3329	6h 25m	97%	82%
Southwest Details →	DAL 06:00 → ATL 09:05WN 1261	55m Atlanta	ATL 10:00 → MDW 11:00WN 224	5h 00m	91%	81%
Delta Details →	DAL 06:05 → ATL 09:15DL 516	1h 50m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 00m	96%	80%
Southwest Details →	DAL 06:05 → MCI 07:35WN 4631	53m Kansas City	MCI 08:28 → MDW 09:52WN 1774	3h 48m	90%	79%
Southwest Details →	DAL 06:00 → HOU 07:10WN 1628	1h 00m Houston	HOU 08:10 → MDW 10:40WN 1294	4h 40m	93%	78%
Tight connection: often missed
Southwest Details →	DAL 10:40 → LAS 11:25WN 486	1h 10m Las Vegas	LAS 12:35 → MDW 18:10WN 2273	7h 30m	73%	39%
Southwest Details →	DAL 11:40 → BWI 15:35WN 2595	53m Baltimore	BWI 16:28 → MDW 17:32WN 997	5h 53m	43%	26%
Southwest Details →	DAL 17:55 → DEN 19:25WN 1303	1h 25m Denver	DEN 20:50 → MDW 00:15 +1WN 1615	6h 17m	63%	22%

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

TPA · 1h 10m · leaves 06:10 2%

HOU · 1h 00m · leaves 06:00 7%

ATL · 55m · leaves 06:00 9%

Afternoon and evening

HOU · 1h 05m · leaves 16:30 27%

BWI · 53m · leaves 11:40 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.


Southwest WN 1261 DAL 06:00 → ATL Delta DL 2417 ATL 11:05 → MDW Connection details →	2h 00m	6h 05m	98%	85%
Southwest WN 1766 DAL 09:30 → ATL Delta DL 1728 ATL 15:15 → MDW Connection details →	2h 40m	6h 45m	100%	73%
Delta DL 516 DAL 06:05 → ATL Southwest WN 225 ATL 12:30 → MDW Connection details →	3h 15m	7h 20m	97%	72%

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