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 90-minute layover misses 5% of the time at 9 am and 1 time in 4 at 7 pm.

Nonstops (seasonal or thin)


Southwest	MKE	SAN	4h 20m	72%	0.0%	193	Flying now

Best connections, any airlines

Most reliable Quickest (80%+ on time)

Ranked by chance you reach San Diego on time. Total trip = scheduled departure to arrival, layover included (San Diego is 2 h behind Milwaukee). Layovers up to 4 hours. Pick a connection for the details.


United Details →	MKE 08:16 → DEN 10:05UA 5558 · flown by SkyWest	3h 25m Denver	DEN 13:30 → SAN 14:55UA 1302	8h 39m	100%	87%
Southwest Details →	MKE 05:15 → DEN 06:50WN 2942	1h 25m Denver	DEN 08:15 → SAN 09:40WN 1699	6h 25m	100%	86%
United Details →	MKE 10:44 → DEN 12:33UA 5536 · flown by SkyWest	3h 22m Denver	DEN 15:55 → SAN 17:20UA 1281	8h 36m	100%	85%
Delta Details →	MKE 05:40 → ATL 08:42DL 1221	3h 11m Atlanta	ATL 11:53 → SAN 13:21DL 540	9h 41m	96%	81%
Alaska + Deltatwo ticketsDetails →	MKE 06:02 → SEA 08:31AS 440	3h 34m Seattle	SEA 12:05 → SAN 15:04DL 2572	11h 02m	100%	81%
Delta Details →	MKE 06:20 → MSP 07:43DL 4460 · flown by SkyWest	3h 55m Minneapolis	MSP 11:38 → SAN 13:29DL 2125	9h 09m	98%	80%
American + Unitedtwo ticketsDetails →	MKE 05:02 → ORD 06:14AA 6358 · flown by SkyWest	2h 32m Chicago	ORD 08:46 → SAN 11:21UA 660	8h 19m	96%	79%
Delta Details →	MKE 10:11 → ATL 13:14DL 2999	2h 22m Atlanta	ATL 15:36 → SAN 17:00DL 843	8h 50m	99%	79%
Tight connection: often missed
Delta Details →	MKE 13:22 → DTW 15:37DL 5476 · flown by Endeavor	58m Detroit	DTW 16:35 → SAN 18:21DL 369	6h 59m	67%	50%
Southwest Details →	MKE 18:35 → DEN 20:20WN 3885	1h 10m Denver	DEN 21:30 → SAN 23:00WN 1704	6h 20m	66%	33%
American Details →	MKE 18:40 → DFW 21:17AA 2136	1h 38m Dallas-Fort Worth	DFW 22:55 → SAN 23:59AA 2568	7h 19m	54%	28%

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

PHX · 50m · leaves 05:25 5%

ORD · 1h 16m · leaves 06:20 5%

DEN · 1h 10m · leaves 08:16 8%

Afternoon and evening

DTW · 58m · leaves 13:22 33%

DEN · 1h 10m · leaves 18:35 34%

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