Cheap flights from Chicago to Miami from $103

The month of January is, on average, the cheapest month to fly to Miami from Chicago, with most prices found around $231. If you are unable to visit Miami during the month of January, then departing from Chicago during the month February is also very affordable. Most momondo users find prices during this month for around $257.

The cheapest day to depart from Chicago to Miami is on a Monday when prices can be found for as low as $427. 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 $502.

In the evening is the cheapest time of day to fly from Chicago to Miami when you can find flight prices for as low as $399. 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 afternoon because they tend to be around $457. 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 - Miami flight prices

You are more likely to see cheaper flights to Miami from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Miami for around $304 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Miami from Chicago for as low as $238 on momondo.

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

No. A direct flight is the cheapest option for a flight between Chicago to Miami.

As of September 2026, prices for Chicago to Miami flights are approximately 52% more expensive when compared to flights at the same time last year.

Southwest and United Airlines are the most popular carriers operating from Chicago to Miami

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Miami from Chicago according to our data. American Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Miami. Keep in mind that there are 7 different airlines that fly to Miami on a routine basis, so you have a few additional options to choose from.

Historically, on average around 19% 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 147 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.

Wednesday 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, United Airlines 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.

As of September 2026, there are 44 flights per day flying from Chicago to Miami. The most common time of day flights depart is 7:00AM, with 53% of flights taking off at noon.

As of September 2026, there are 314 flights per week flying from Chicago to Miami. The most common day of the week flights depart is Thu, with 16% of flights taking off on this day.