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

No clear winner: airlines and hours on this route all land within a few points of 3 in 4 on time.

Nonstops


Southwest	MDW	DTW	1h 10m	75%	1.9%	1,050	Flying now
Delta	MDW	DTW	1h 14m	75%	1.4%	1,064	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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


Delta Details →	MDW 09:54 → MSP 11:35DL 5469 · flown by Endeavor	1h 20m Minneapolis	MSP 12:55 → DTW 15:38DL 1519	4h 44m	93%	84%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	2h 05m Atlanta	ATL 11:00 → DTW 12:55DL 1240	5h 56m	95%	78%
Delta Details →	MDW 11:05 → ATL 14:01DL 1063	3h 09m Atlanta	ATL 17:10 → DTW 19:11DL 2067	7h 06m	99%	72%
Delta Details →	MDW 12:50 → ATL 15:49DL 2417	2h 22m Atlanta	ATL 18:11 → DTW 20:14DL 1478	6h 23m	97%	71%
Delta Details →	MDW 17:10 → ATL 20:22DL 1728	2h 37m Atlanta	ATL 22:59 → DTW 00:59 +1DL 2940	6h 49m	95%	67%
Frontier Details →	MDW 06:00 → ATL 09:19F9 2292	2h 21m Atlanta	ATL 11:40 → DTW 13:44F9 2898	6h 44m	98%	60%
Delta Details →	MDW 13:49 → MSP 15:33DL 4820 · flown by Endeavor	2h 03m Minneapolis	MSP 17:36 → DTW 20:22DL 1435	5h 33m	83%	59%
Southwest Details →	MDW 17:20 → BWI 20:15WN 4616	2h 25m Baltimore	BWI 22:40 → DTW 00:20 +1WN 942	5h 55m	80%	52%
Tight connection: often missed
Southwest Details →	MDW 09:55 → DEN 11:30WN 2654	50m Denver	DEN 12:20 → DTW 17:05WN 1526	6h 10m	56%	35%
Southwest Details →	MDW 18:40 → BNA 20:10WN 1073	1h 20m Nashville	BNA 21:30 → DTW 00:08 +1WN 2210	4h 28m	69%	28%
Southwest Details →	MDW 16:15 → DEN 18:00WN 2769	1h 05m Denver	DEN 19:05 → DTW 23:55WN 2193	6h 40m	64%	18%

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

MSP · 1h 20m · leaves 09:54 7%

Afternoon and evening

BNA · 1h 20m · leaves 18:40 31%

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 3877 MDW 10:05 → IND Delta DL 5846 IND 16:00 → DTW Connection details →	3h 52m	6h 15m	100%	92%
Southwest WN 1243 MDW 07:40 → MSP Delta DL 1519 MSP 12:55 → DTW Connection details →	3h 45m	6h 58m	100%	91%
Southwest WN 852 MDW 07:40 → RDU Delta DL 2265 RDU 13:00 → DTW Connection details →	2h 25m	6h 18m	100%	90%

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