Cheap flights from Florida to Chicago from £74

The cheapest month to fly to Chicago from Florida is in January. Flight prices, which tend to average around £137, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Chicago from Florida during October instead. Flights to Chicago in October, while not as cheap as those in January, still average around £159.

Flying to Chicago from Florida at midday is the least expensive time of day to depart. momondo users have found prices as low as £225 when looking at flights departing at midday. Flights in the morning are often more expensive, with an average ticket price of £387.

Fly from Tampa to Chicago Midway 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 £174 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 £135 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.

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

As of July 2026, there are 110 flights per day flying from Florida to Chicago. The most common time of day flights depart is 12:00, with 53% of flights taking off in the afternoon.

As of July 2026, 773 flights take off from Florida and land in Chicago each week. The most common flight departure day for this route is Fri, with 18% of weekly flights taking off on this day.