Cheap flights from Florida to Chicago from £42

The cheapest month to fly to Chicago from Florida is in September. Flight prices, which tend to average around £83, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from Florida during October instead. Flights to Chicago in October, while not as cheap as those in September, still average around £114.

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as £199. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Friday, with ticket prices averaging around £407.

Flying to Chicago from Florida in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as £239 when looking at flights departing in the afternoon. Flights at midday are often more expensive, with an average ticket price of £442.

Fly from Palm Beach Intl to Chicago O'Hare Intl for the best Florida - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Florida when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £157 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Florida for as low as £123 on momondo.

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

As of February 2026, there are 97 flights per day flying from Florida to Chicago. The most common time of day flights depart is 16:00, with 49% of flights taking off in the afternoon.

As of February 2026, 684 flights take off from Florida and land in Chicago each week. The most common flight departure day for this route is Fri, with 20% of weekly flights taking off on this day.