Cheap flights from Chicago to Florida from £30

The cheapest month to fly to Florida from Chicago is in August. Flight prices, which tend to average around £128, are often lower during this time because this is during the off-season. If you’re not able to fly to Florida in August, then September is your next best option. Flight prices from Chicago to Florida during September average around £145.

The cheapest day to depart from Chicago to Florida is on a Tuesday. Travellers who choose to depart for Florida on a Tuesday will often find tickets for as low as £95. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around £506. These prices are subject to change though, so be sure to set up a Price Alert for flights to Florida.

According to our data, the cheapest time of day to fly to Florida is in the afternoon. momondo users have found flights departing from Chicago to Florida in the afternoon for as low as £101. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Florida is in the morning when prices are around £173.

Fly from Chicago O'Hare Intl to Fort Myers SW Florida Intl 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 £197 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Florida from Chicago for as low as £168 on momondo.

There are 3 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.

The number of flights available between Chicago and Florida is 194 per day as of March 2026. The most frequent departure time is 07:00, with 46% of daily flights leaving at midday.

As of March 2026, there are 1,361 flights per week flying from Chicago to Florida. The most common day of the week flights depart is Wed, with 16% of flights taking off on this day.