Cheap flights from Milwaukee to Orlando from $29

The cheapest month to fly to Orlando Airport from Milwaukee is in January. Flight prices, which tend to average around $217, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Orlando Airport from Milwaukee during February instead. Flights to Orlando Airport in February, while not as cheap as those in January, still average around $303.

The cheapest day to depart from Milwaukee to Orlando Airport is on a Tuesday. Travelers who choose to depart for Orlando Airport on a Tuesday will often find tickets for as low as $302. The most expensive day to fly to Orlando Airport is Wednesday, with ticket prices averaging around $382.

In the evening is the cheapest time of day to fly from Milwaukee to Orlando Airport when you can find flight prices for as low as $256. Flying to Orlando Airport in the evening is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $391.

Fly from Milwaukee-Mitchell to Orlando for the best Milwaukee-Mitchell - Orlando flight prices

You are more likely to see cheaper flights to Orlando Airport from Milwaukee when booking weeks ahead of your departure date. In general, you can expect to find flights to Orlando Airport for around $358 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Orlando Airport from Milwaukee for as low as $235 on momondo.

There are 4 cabin classes available to choose from on Milwaukee to Orlando Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Southwest, Sun Country Air, and Delta are the most popular carriers operating from Milwaukee-Mitchell to Orlando

Frontier, United Airlines and American Airlines are the top three most popular airlines that fly to Orlando Airport from Milwaukee according to our data. Frontier is the first choice among our users, with 31% of people opting to fly with this airline when traveling to Orlando Airport. Keep in mind that there are 8 different airlines that fly to Orlando Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 14% of flights between Milwaukee and Orlando have experienced a delay on any given week. The average delay length over the past 12 months has been 139 minutes.

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 14% of their flights experiencing any sort of delay.

As of October 2026, 1 flights take off from Milwaukee and land in Orlando Airport each day. The most common flight departure time for this route is 1:00PM, with 40% of daily flights taking off in the afternoon.

The number of flights available between Milwaukee and Orlando Airport is 11 per week as of October 2026. The most frequent departure day is Fri, with 36% of weekly flights leaving on this day.