Cheap flights from Chicago Midway Airport to Miami from $66

The month of October is, on average, the cheapest month to fly to Miami from Chicago Midway Airport, with most prices found around $149. If you are unable to visit Miami during the month of October, then departing from Chicago Midway Airport during the month March is also very affordable. Most momondo users find prices during this month for around $290.

The cheapest day to depart from Chicago Midway Airport to Miami is on a Monday when prices can be found for as low as $335. Be sure to avoid booking your departure on a Tuesday as prices are generally higher than usual. According to our data, the average ticket price to Miami on Tuesday is $407.

In the evening is the cheapest time of day to fly from Chicago Midway Airport to Miami when you can find flight prices for as low as $275. Flying to Miami in the evening is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the morning because they tend to be around $388. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Chicago Midway to Miami for the best Chicago Midway - Miami flight prices

You are more likely to see cheaper flights to Miami from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Miami for around $318 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Miami from Chicago Midway Airport for as low as $213 on momondo.

Southwest and Delta are the most popular carriers operating from Chicago Midway to Miami

Southwest, Frontier and Delta are the top three most popular airlines that fly to Miami from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 58% of people opting to fly with this airline when traveling to Miami. Keep in mind that there are 5 different airlines that fly to Miami on a routine basis, so you have a few additional options to choose from.

Historically, on average around 22% of flights between Chicago and Miami have experienced a delay on any given week. The average delay length over the past 12 months has been 146 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights at night 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. Monday 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 17% of their flights experiencing any sort of delay.

The number of flights available between Chicago Midway Airport and Miami is 2 per day as of April 2026. The most frequent departure time is 8:00AM, with 71% of daily flights leaving at noon.

As of April 2026, there are 14 flights per week flying from Chicago Midway Airport to Miami. The most common day of the week flights depart is Mon, with 29% of flights taking off on this day.