Cheap flights from Florida Keys to Chicago from $62

The month of February is, on average, the cheapest month to fly to Chicago from Florida Keys, with most prices found around $148. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Florida Keys to Chicago during January average around $157.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $286. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Florida Keys to Chicago for around $507.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Florida Keys to Chicago during this time can be as low as $293. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $381.

Fly from Key West to Chicago O'Hare Intl for the best Florida Keys - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Florida Keys when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $240 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Florida Keys for as low as $165 on momondo.

There are 4 cabin classes available to choose from on Florida Keys 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 April 2026, there are 45 flights per day flying from Florida Keys to Chicago. The most common time of day flights depart is 3:00PM, with 81% of flights taking off in the afternoon.

318 flights are operational weekly from Florida Keys to Chicago as of April 2026. The most popular departure day for this route is Sat, with 19% of flights per week taking off on this day.