Cheap Flights from Chicago to Jacksonville International

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Flight deals from Chicago to Jacksonville International

Looking for a cheap last-minute deal or the best return flight from Chicago to Jacksonville International? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Jacksonville International

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Jacksonville International flights are currently cheapest in October.

Direct flights from Chicago to Jacksonville International

Chicago to Jacksonville International: Alternative routes

Compare routes from Chicago to Jacksonville below. You may find an airport to fly into that's cheaper, faster, or easier than Jacksonville International.

Chicago to Jacksonville: Flight information

The things to know before you go.
Cheapest flight foundR 1,246
Cheapest month to flyOctober
Average flight time2 hrs, 23 mins
Most popular airlineAmerican Airlines
Average flights per week204

Finding cheap flights from Chicago to Jacksonville International: Frequently asked questions

The best price we found for a return flight from Chicago to Jacksonville International is R 2,485. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 22 minutes is the average flight time from Chicago to Jacksonville International.
American Airlines, Alaska Airlines and United fly direct from Chicago to Jacksonville International.
As of October 2025, there are 204 flights per week flying from Chicago to Jacksonville International.
The cheapest month to fly from Chicago to Jacksonville International is usually November.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Jacksonville International Airport on Sunday, 2 November 2025.
Yes – the average flight time is 2 hours and 22 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Jacksonville International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Jacksonville is around 40 days in advance, so don’t leave your flight to the last minute.

Travelling from Chicago to Jacksonville International Airport (JAX): What you need to know

  • Begin your travels at one of Chicago's main airports, O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Check out your options for booking a flight from Chicago to Jacksonville International Airport (JAX) taking off from either of these.

  • 2 hours 25 minutes is the average travel time for a direct Chicago to Jacksonville International Airport flight.

  • The timezone in Jacksonville is UTC-4, which is one hour ahead of Chicago. Jacksonville International Airport is located in Jacksonville.

  • With 34 direct flights a week between the two airports, O'Hare International Airport (ORD) to Jacksonville International Airport (JAX) is the busiest route. American Airlines operates the earliest flight at 7am. If you prefer to get more out of your day before flying, the latest flight from ORD to JAX is with American Airlines at 8:20pm.

  • To ensure you catch your flight from Chicago to JAX, leave plenty of time to navigate the airport and find your gate. Arriving two hours ahead of international departures and an hour before domestic flights is the general travel rule.

  • Peak season means busier airports, so aim to get there even earlier. Give yourself at least two hours before a domestic flight and four hours for international journeys to keep to your schedule.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) provides a hassle-free way to reach your destination. Nonstop flights from Chicago to Jacksonville International Airport (JAX) leave from this terminal.

  • United Airlines is a popular carrier that operates direct flights from Chicago to Jacksonville International Airport taking off from ORD.

  • United Airlines is the airline most travellers choose for flights from ORD to JAX.

  • American Airlines is the top performer for punctuality on this route.

  • ORD is around 40 kilometres from central Chicago. If you're driving, ride-sharing or catching a cab from the centre, it'll take 35 minutes or so to get there, depending on traffic. If you're using public transport, expect the journey time to be around 55 minutes.

  • Want a hassle-free start to your trip? Stay near O'Hare International Airport. Whether you've booked an early flight from Chicago to Jacksonville International Airport or want to avoid feeling rushed, these hotels are the answer:

  • When it comes to the on-time performance of O'Hare International Airport, data shows 74.85% of flights stick to their scheduled arrival time.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Consider starting your trip from Chicago Midway International Airport (MDW). You can book a direct Chicago to Jacksonville International Airport (JAX) plane ticket from this popular hub.

  • You can board a direct flight from Chicago to JAX with Southwest Airlines. This is one of the top airlines that operates this route out of MDW.

  • Southwest Airlines is the most popular choice for travellers flying from MDW to JAX.

  • Southwest Airlines is the most reliable carrier flying from Chicago Midway International Airport to Jacksonville International Airport, with 79.66% of its services landing on schedule.

  • You can reach MDW from the centre of Chicago in about 20 minutes by car (depending on traffic conditions). The ride by public transport takes roughly 45 minutes to cover the 19 kilometres or so.

  • Get your holiday started early with an extra night away from home. Before your Chicago to JAX flight, stay in one of these hotels near Chicago Midway International Airport:

  • When it comes to flight punctuality, Chicago Midway International Airport has an on-time arrival rate of 77.88%.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • The journey time to RFD from the centre of Chicago is around 4 hours 15 minutes by public transport. If you prefer to travel by car, it'll take you roughly 1 hour 25 minutes to cover the 137 kilometres or so.

  • Stay in bed a little longer and still make your Chicago to Jacksonville International Airport flight with time to spare. These accommodation options near Chicago Rockford International Airport make it a breeze to get to the terminal if you're setting off early:

  • Flights that depart from RFD make it to their destination on schedule 76.19% of the time.

  • You'll find Chicago Rockford International Airport at 2 Airport Cir.

About Jacksonville International Airport (JAX)

Getting from Jacksonville International Airport (JAX) to central Jacksonville

  • Central Jacksonville is around 18 kilometres from Jacksonville International Airport. Travel times by cab or car hire will vary based on time of day and traffic conditions, so do a little research before you go.

  • Travelling by public transport will take you roughly 1 hour 20 minutes.

How to find the cheapest flights from Chicago to Jacksonville International Airport (JAX)

  • Currently, R 1,246 is the best price we've found for a one-way ticket from Chicago to Jacksonville International Airport. The cheapest price for a return flight is R 2,485. Keep in mind fares may change due to availability at the time of booking.

  • Score cheap flights from Chicago to JAX by booking one month ahead. Based on our research, that's the ideal time frame for finding a bargain.

  • Plan your trip for June. That's the best month for landing the biggest deals on Chicago to Jacksonville International Airport tickets. If your travel dates are flexible, use the 'Whole month' tool to find the cheapest price across every month.

  • Locking in a cheap plane ticket from Chicago to JAX is easy with Price Alerts. Simply set up one of these automatic alerts and we'll notify you when prices go down.

  • Find an affordable flight from Chicago to Jacksonville International Airport by using the search filters. Choose your ideal duration, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

The best time to fly from Chicago to Jacksonville International Airport (JAX)

  • It's time to decide when to book your flight from Chicago to Jacksonville International Airport (JAX). July is when most people travel to Jacksonville. If you like your getaways a little more chill, head there in May.

  • Lock in a Chicago to JAX plane ticket departing in July if you want to explore the city during its warmest month. You can expect temperatures in Jacksonville to range from 23ºC (73ºF) to 34ºC (93ºF).

  • Look for cheap tickets from Chicago to Jacksonville International Airport in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between 5ºC (41ºF) and 21ºC (70ºF).

More about Jacksonville

  • Once you've booked your flight from Chicago to Jacksonville International Airport, find a hotel that's got location and comfort covered. Make one of these options your base for exploring Jacksonville:

  • There are so many things to discover in this city, it can be difficult to know where to begin. St. John's Cathedral, San Marco Historic District and Museum of Contemporary Art Jacksonville are popular attractions which should be on any well-planned Jacksonville itinerary.

Explore more of the United States

  • Jacksonville will leave a lasting impression, but there are so many other parts of the United States you should also see. Around 290 kilometres south of Jacksonville, a visit to Tampa will fill your itinerary to the brim. Start with attractions like Super Bowl, Busch Gardens Tampa and The Florida Aquarium.

  • Orlando is another essential stop in the United States and is around 225 kilometres south of Jacksonville. No journey is complete without a visit to Hogwarts, Universal's Islands of Adventure and Hogwarts Express.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.