Cheap flights from Chicago to Jacksonville from $99

If you are unable to visit Jacksonville during the month of September, then departing from Chicago during the month August is also very affordable. Most momondo users find prices during this month for around $317.

According to our data, Saturday is the cheapest day to fly to Jacksonville from Chicago. The lowest ticket price found for a Saturday departure recently was $342. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $414.

Flying to Jacksonville from Chicago at noon is the least expensive time of day to depart. momondo users have found prices as low as $347 when looking at flights departing at noon. Flights to Jacksonville are more costly in the afternoon, with an average ticket price of $374. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

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

You are more likely to see cheaper flights to Jacksonville from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Jacksonville for around $363 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Jacksonville from Chicago for as low as $313 on momondo.

There are 4 cabin classes available to choose from on Chicago to Jacksonville 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 Jacksonville.

As of August 2026, prices for Chicago to Jacksonville flights are approximately 18% more expensive when compared to flights at the same time last year.

Southwest, Delta, and United Airlines are the most popular carriers operating from Chicago to Jacksonville

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Jacksonville from Chicago according to our data. United Airlines is the first choice among our users, with 47% of people opting to fly with this airline when traveling to Jacksonville. Keep in mind that there are 6 different airlines that fly to Jacksonville on a routine basis, so you have a few additional options to choose from.

Atlanta (ATL) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.

Flights via Atlanta (ATL) offer the lowest average round-trip price of $140.

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 4h 14m.

Atlanta (ATL) has the shortest average layover time for this route: 0h 56m.

20 flights are operational daily from Chicago to Jacksonville as of August 2026. The most popular departure time for this route is 7:00PM, with 49% of flights per day taking off in the evening.

As of August 2026, there are 141 flights per week flying from Chicago to Jacksonville. The most common day of the week flights depart is Wed, with 19% of flights taking off on this day.