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 MKE → MDW flights land within a few points of 73% on time whatever the hour.

Nonstops (seasonal or thin)


Southwest	MKE	MDW	50m	73%	1.7%	298	Flying now

Best connections, any airlines

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 →	MKE 06:00 → AUS 08:40WN 4866	1h 45m Austin	AUS 10:25 → MDW 12:55WN 4077	6h 55m	96%	84%
Delta Details →	MKE 05:40 → ATL 08:42DL 1221	2h 23m Atlanta	ATL 11:05 → MDW 12:05DL 2417	6h 25m	96%	81%
Southwest Details →	MKE 07:40 → BNA 09:10WN 4598	3h 45m Nashville	BNA 12:55 → MDW 14:30WN 1430	6h 50m	100%	78%
Southwest Details →	MKE 08:15 → DCA 11:00WN 311	1h 00m Washington	DCA 12:00 → MDW 13:00WN 1445	4h 45m	90%	77%
Delta + Southwesttwo ticketsDetails →	MKE 06:20 → MSP 07:43DL 4460 · flown by SkyWest	2h 42m Minneapolis	MSP 10:25 → MDW 11:55WN 4345	5h 35m	95%	76%
Delta Details →	MKE 07:12 → DTW 09:30DL 3757 · flown by SkyWest	2h 55m Detroit	DTW 12:25 → MDW 12:46DL 4688 · flown by Endeavor	5h 34m	92%	74%
Delta Details →	MKE 14:59 → ATL 18:06DL 1246	3h 09m Atlanta	ATL 21:15 → MDW 22:17DL 1076	7h 18m	99%	74%
Delta Details →	MKE 10:11 → ATL 13:14DL 2999	2h 01m Atlanta	ATL 15:15 → MDW 16:15DL 1728	6h 04m	99%	72%

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

ATL · 1h 05m · leaves 06:50 10%

DCA · 1h 00m · leaves 08:15 10%

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