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

The nonstop is quickest: Southwest SAN → MKE (4h 00m), on time 3 times in 4. Southwest via Denver (7h 00m) is more reliable, 89%, but takes 3h 00m longer.

Nonstops (seasonal or thin)


Southwest	SAN	MKE	4h 00m	74%	0.0%	193	Flying now

Best connections, one ticket

Most reliable Quickest (80%+ on time)

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


Delta Details →	SAN 22:15 → DTW 05:43DL 764	2h 52m Detroit	DTW 08:35 → MKE 08:51 +1DL 3191	8h 36m	100%	90%
Southwest Details →	SAN 10:45 → DEN 14:08WN 3495	2h 12m Denver	DEN 16:20 → MKE 19:45WN 1629	7h 00m	96%	89%
Southwest Details →	SAN 22:40 → BNA 04:45WN 3480	3h 25m Nashville	BNA 08:10 → MKE 09:45 +1WN 585	9h 05m	100%	87%
United Details →	SAN 06:35 → DEN 10:08UA 2368	3h 22m Denver	DEN 13:30 → MKE 17:04UA 4802 · flown by SkyWest	8h 29m	100%	87%
Delta Details →	SAN 22:30 → ATL 05:50DL 819	2h 15m Atlanta	ATL 08:05 → MKE 09:06 +1DL 2999	8h 36m	99%	86%
Southwest Details →	SAN 21:55 → MCO 05:55WN 4874	1h 25m Orlando	MCO 07:20 → MKE 09:10 +1WN 4459	9h 15m	89%	86%
Delta Details →	SAN 21:54 → BOS 06:30DL 571	2h 40m Boston	BOS 09:10 → MKE 10:54 +1DL 5614 · flown by Republic	10h 57m	98%	86%
United Details →	SAN 06:15 → IAH 11:42UA 2760	2h 38m Houston	IAH 14:20 → MKE 17:06UA 6164 · flown by Mesa	8h 51m	100%	81%
Tight connection: often missed
United Details →	SAN 14:00 → ORD 20:20UA 1779	1h 00m Chicago	ORD 21:20 → MKE 22:29UA 5362 · flown by SkyWest	6h 29m	70%	47%
Delta Details →	SAN 11:37 → DTW 19:09DL 492	51m Detroit	DTW 20:00 → MKE 20:22DL 3724 · flown by SkyWest	6h 45m	69%	44%
United Details →	SAN 10:35 → ORD 16:52UA 1710	53m Chicago	ORD 17:45 → MKE 18:48UA 5555 · flown by SkyWest	6h 13m	74%	36%

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

LAS · 50m · leaves 06:35 10%

Afternoon and evening

DTW · 51m · leaves 11:37 31%

ORD · 52m · leaves 09:58 32%

DEN · 48m · leaves 16:07 37%

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.


Alaska AS 707 SAN 21:06 → MCO Southwest WN 4459 MCO 07:20 → MKE Connection details →	2h 02m	10h 04m	94%	92%
Alaska AS 1618 SAN 07:00 → DEN United UA 4802 DEN 13:30 → MKE Connection details →	2h 57m	8h 04m	100%	89%
Frontier F9 4990 SAN 10:00 → DEN Southwest WN 1629 DEN 16:20 → MKE Connection details →	2h 43m	7h 45m	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