Cheap flights from Miami to Chicago from $106

The month of February is, on average, the cheapest month to fly to Chicago from Miami, with most prices found around $157. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Miami to Chicago during January average around $172.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $401. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Miami to Chicago for around $616.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Miami to Chicago during this time can be as low as $358. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $486.

Fly from Miami to Chicago O'Hare Intl for the best Miami - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Miami when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $316 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Miami for as low as $242 on momondo.

There are 4 cabin classes available to choose from on Miami to Chicago 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 Miami to Chicago.

As of October 2026, prices for Miami to Chicago flights are approximately 2% more expensive when compared to flights at the same time last year.

Frontier, United Airlines, and Delta are the most popular carriers operating from Miami to Chicago

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Chicago from Miami according to our data. American Airlines is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 17% of flights between Miami and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 149 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon 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, United Airlines have had the least number of delays on this route over the last 12 months; with about 12% of their flights experiencing any sort of delay.

As of October 2026, 37 flights take off from Miami and land in Chicago each day. The most common flight departure time for this route is 3:00PM, with 44% of daily flights taking off in the afternoon.

As of October 2026, 260 flights take off from Miami and land in Chicago each week. The most common flight departure day for this route is Sun, with 22% of weekly flights taking off on this day.