Cheap flights from Chicago to Florida from $66

In general, January is the cheapest month to fly from Chicago to Florida. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $226. If you’re not able to fly to Florida in January, then February is your next best option. Flight prices from Chicago to Florida during February average around $258.

On average, the least expensive day to fly to Florida from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $290. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Florida on Sunday is $354.

Flying to Florida from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $280 when looking at flights departing in the afternoon. Flights to Florida are more costly in the morning, with an average ticket price of $340. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

Fly from Chicago Greater Rockford to Fort Lauderdale for the best Chicago - Florida flight prices

You are more likely to see cheaper flights to Florida from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Florida for around $307 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Florida from Chicago for as low as $265 on momondo.

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

United Airlines, JetBlue, and Southwest are the most popular carriers operating from Chicago to Florida

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

As of September 2026, there are 132 flights per day flying from Chicago to Florida. The most common time of day flights depart is 7:00PM, with 45% of flights taking off at noon.

925 flights are operational weekly from Chicago to Florida as of September 2026. The most popular departure day for this route is Wed, with 20% of flights per week taking off on this day.