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 14% of the time at 8 am and 30% of the time at 8 pm.

Nonstops


Southwest	DTW	MDW	1h 10m	75%	1.3%	1,052	Flying now
Delta	DTW	MDW	1h 21m	71%	1.4%	1,064	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 Detroit). Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	DTW 07:00 → STL 07:35WN 1783	1h 20m St Louis	STL 08:55 → MDW 10:00WN 2570	4h 00m	98%	86%
Southwest Details →	DTW 06:30 → BNA 07:05WN 4581	2h 15m Nashville	BNA 09:20 → MDW 11:00WN 1473	5h 30m	98%	84%
Delta Details →	DTW 06:17 → ATL 08:12DL 1611	2h 53m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 48m	98%	84%
Delta Details →	DTW 05:17 → ATL 07:10DL 2375	1h 59m Atlanta	ATL 09:09 → MDW 10:09DL 1063	5h 52m	95%	80%
Delta Details →	DTW 10:25 → ATL 12:25DL 2856	2h 50m Atlanta	ATL 15:15 → MDW 16:15DL 1728	6h 50m	98%	73%
Delta Details →	DTW 16:00 → ATL 18:04DL 1467	3h 11m Atlanta	ATL 21:15 → MDW 22:17DL 1076	7h 17m	98%	73%
Southwest Details →	DTW 05:50 → BWI 07:20WN 4534	2h 15m Baltimore	BWI 09:35 → MDW 10:35WN 4217	5h 45m	100%	68%
Delta Details →	DTW 12:20 → MSP 13:14DL 2697	3h 24m Minneapolis	MSP 16:38 → MDW 18:18DL 4714 · flown by Endeavor	6h 57m	100%	58%
Tight connection: often missed
Delta Details →	DTW 18:09 → ATL 20:19DL 2053	56m Atlanta	ATL 21:15 → MDW 22:17DL 1076	5h 08m	70%	53%
Delta Details →	DTW 12:25 → ATL 14:23DL 2188	52m Atlanta	ATL 15:15 → MDW 16:15DL 1728	4h 50m	60%	45%
Southwest Details →	DTW 20:15 → STL 20:50WN 4159	55m St Louis	STL 21:45 → MDW 22:55WN 3957	3h 35m	40%	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

STL · 1h 20m · leaves 07:00 2%

ATL · 57m · leaves 06:17 14%

Afternoon and evening

ATL · 56m · leaves 18:09 30%

DEN · 1h 12m · leaves 16:42 49%

STL · 55m · leaves 20:15 60%

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 1439 DTW 07:00 → CLT Southwest WN 4529 CLT 11:35 → MDW Connection details →	2h 41m	6h 35m	97%	94%
Delta DL 5522 DTW 10:05 → ALB Southwest WN 164 ALB 15:20 → MDW Connection details →	3h 33m	7h 30m	95%	87%
Delta DL 4055 DTW 08:30 → OMA Southwest WN 4470 OMA 13:10 → MDW Connection details →	3h 27m	7h 05m	96%	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