Cheap flights from Chicago to Florida from £54

The cheapest month to fly to Florida from Chicago is in January. Flight prices, which tend to average around £168, are often lower during this time because this is during the off-season. If you’re not able to fly to Florida in January, then October is your next best option. Flight prices from Chicago to Florida during October average around £182.

The cheapest day to depart from Chicago to Florida is on a Friday. Travellers who choose to depart for Florida on a Friday will often find tickets for as low as £107. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around £499. These prices are subject to change though, so be sure to set up a Price Alert for flights to Florida.

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 £221 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 £185 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.

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

The number of flights available between Chicago and Florida is 173 per day as of August 2026. The most frequent departure time is 18:00, with 43% of daily flights leaving at midday.

As of August 2026, there are 1,213 flights per week flying from Chicago to Florida. The most common day of the week flights depart is Sun, with 16% of flights taking off on this day.