Cheap flights from San Diego to Milwaukee from $149

The cheapest month to fly to Milwaukee from San Diego is in September. Flight prices, which tend to average around $309, are often lower during this time because this is during the off-season. The month of November is another great option to travel to Milwaukee, with average flight prices from San Diego averaging around $325.

According to our data, Friday is the cheapest day to fly to Milwaukee from San Diego. The lowest ticket price found for a Friday departure recently was $387. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. Flights from San Diego to Milwaukee on a Sunday will generally be more expensive and average around $657. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

In the afternoon is the cheapest time of day to fly from San Diego to Milwaukee when you can find flight prices for as low as $397. Flying to Milwaukee in the afternoon is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Milwaukee, so prices are often more expensive at around $514 per ticket.

Fly from San Diego to Milwaukee-Mitchell for the best San Diego - Milwaukee-Mitchell flight prices

You are more likely to see cheaper flights to Milwaukee from San Diego when booking weeks ahead of your departure date. In general, you can expect to find flights to Milwaukee for around $395 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milwaukee from San Diego for as low as $289 on momondo.

No. A direct flight is the cheapest option for a flight between San Diego to Milwaukee.

As of May 2026, prices for San Diego to Milwaukee flights are approximately 2% more expensive when compared to flights at the same time last year.

Delta and United Airlines are the most popular carriers operating from San Diego to Milwaukee-Mitchell

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Milwaukee from San Diego according to our data. American Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Milwaukee. Keep in mind that there are 9 different airlines that fly to Milwaukee on a routine basis, so you have a few additional options to choose from.

Chicago (ORD) was the most common stop: 40% of momondo users choosing 1-stop flights on this route connected there.

Flights via Minneapolis (MSP) offer the lowest average round-trip price of $276.

Flights connecting via Phoenix (PHX) have the shortest average one-way travel time: 5h 45m.

Chicago (ORD) has the shortest average layover time for this route: 0h 46m.