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

Take the nonstop: Southwest MDW → MKE (45m) reaches Milwaukee on time 2 times in 3; the most reliable connection, Delta via Detroit (3h 27m), 52%.

Nonstops (seasonal or thin)


Southwest	MDW	MKE	45m	70%	3.0%	298	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

Ranked by chance you reach Milwaukee on time. Total trip = scheduled departure to arrival, layover included. Layovers up to 4 hours. Pick a connection for the details.


Southwest Details →	MDW 06:50 → DEN 08:20WN 2765	1h 55m Denver	DEN 10:15 → MKE 13:40WN 1626	6h 50m	100%	97%
Southwest + Deltatwo ticketsDetails →	MDW 07:15 → ATL 10:05WN 3054	2h 48m Atlanta	ATL 12:53 → MKE 13:50DL 1246	6h 35m	100%	87%
Southwest + Deltatwo ticketsDetails →	MDW 05:15 → LGA 08:15WN 2801	2h 50m New York	LGA 11:05 → MKE 12:36DL 5723 · flown by Republic	7h 25m	100%	85%
Delta Details →	MDW 06:00 → ATL 08:55DL 1285	1h 55m Atlanta	ATL 10:50 → MKE 11:51DL 1151	5h 51m	94%	81%
Delta Details →	MDW 09:54 → MSP 11:35DL 5469 · flown by Endeavor	2h 19m Minneapolis	MSP 13:54 → MKE 15:08DL 2006	5h 14m	98%	81%
Southwest Details →	MDW 07:00 → BWI 09:45WN 2742	1h 00m Baltimore	BWI 10:45 → MKE 11:50WN 1011	4h 50m	91%	80%
Southwest + Deltatwo ticketsDetails →	MDW 08:55 → ATL 11:45WN 4154	2h 20m Atlanta	ATL 14:05 → MKE 15:07DL 2152	6h 12m	98%	79%
Southwest + Deltatwo ticketsDetails →	MDW 15:30 → MSP 17:00WN 2832	3h 05m Minneapolis	MSP 20:05 → MKE 21:28DL 4468 · flown by SkyWest	5h 58m	98%	79%
Tight connection: often missed
Southwest Details →	MDW 16:15 → DEN 18:00WN 2769	1h 05m Denver	DEN 19:05 → MKE 22:25WN 1634	6h 15m	64%	9%

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 · 50m · leaves 09:17 18%

Afternoon and evening

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.

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