Cheap flights from Jacksonville to Chicago from $118

The month of January is, on average, the cheapest month to fly to Chicago from Jacksonville, with most prices found around $309. If you’re not able to fly to Chicago in January, then September is your next best option. Flight prices from Jacksonville to Chicago during September average around $328.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $425. 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 Jacksonville to Chicago for around $667.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Jacksonville to Chicago during this time can be as low as $395. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $582.

Fly from Jacksonville to Chicago Midway for the best Jacksonville - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Jacksonville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $367 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Jacksonville for as low as $284 on momondo.

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

You could potentially save up to 10% on your flight if you consider stops on a Jacksonville to Chicago flight.

As of September 2026, prices for Jacksonville to Chicago flights are approximately 29% more expensive when compared to flights at the same time last year.

Frontier, United Airlines, and JetBlue are the most popular carriers operating from Jacksonville to Chicago

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Chicago from Jacksonville according to our data. American Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of September 2026, there are 20 flights per day flying from Jacksonville to Chicago. The most common time of day flights depart is 12:00PM, with 50% of flights taking off in the afternoon.

As of September 2026, 140 flights take off from Jacksonville and land in Chicago each week. The most common flight departure day for this route is Mon, with 19% of weekly flights taking off on this day.