Cheap Flights from Jacksonville to Chicago

Compare Jacksonville to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from Jacksonville to Chicago

Looking for a cheap last-minute deal or the best return flight from Jacksonville Airport to Chicago? If you want to travel next month, return fares start from R 6,822. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Jacksonville to Chicago

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

Jacksonville to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 2,587
Cheapest month to flyAugust

Finding cheap flights from Jacksonville to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Jacksonville to Chicago is R 5,433. 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.
Currently, there are no airlines that fly direct from Jacksonville to Chicago. But we found flights with one or more stops from R 5,433.
As of June 2026, there are no flights flying from Jacksonville to Chicago.
The cheapest month to fly from Jacksonville to Chicago is usually August.
If you're flying from Jacksonville Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from R 5,433.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Jacksonville Airport to Chicago on Thursday, 13 August 2026.
No airlines currently offer direct flights between Jacksonville Airport and Chicago. Most routes have one or more stops.
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 Chicago 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In June, the average temperature is usually around 19°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Delta offers the cheapest flight tickets to Chicago.

Travelling from Albert J Ellis Airport (OAJ) to Chicago: what you need to know

  • Chicago is one hour behind Jacksonville, where Albert J Ellis Airport is located. Chicago observes the UTC-6 timezone.

  • To avoid rushing for your OAJ to Chicago flight, allow plenty of time to check in and find your gate. Arriving two hours ahead of international departures and an hour before domestic flights is the standard rule.

  • You can expect longer lines during popular months such as September. Arriving up to four hours ahead of international flights and two hours for a domestic departure will give you plenty of time for security and boarding.

  • OAJ is about 18 kilometres from central Jacksonville. If you're driving, ride-sharing or catching a taxi from the centre, it'll take you 20 minutes or so to get there, depending on traffic conditions. If you're taking public transport, expect the travel time to be around 45 minutes.

  • Albert J Ellis Airport scores high marks for on-time performance. 84% of flights that take off from OAJ arrive at their destination without delay.

  • The address for OAJ is 264 State Road 1265.

How to find the cheapest flights from Albert J Ellis Airport (OAJ) to Chicago

  • R 2,587 is the cheapest price we've seen for a one-way Albert J Ellis Airport to Chicago flight. A round-trip plane ticket right now is R 5,433. Depending on when you want to go and the availability, these fares could change.

  • Booking ahead of time is often the key to scoring a cheap flight from OAJ to Chicago. Prices tend to rise as demand increases, so the nearer your departure date, the more you'll likely spend on your ticket.

  • If you have flexibility with your travel dates, take advantage of the 'Whole month' search tool. It'll give you the lowest price across each month when looking for your Albert J Ellis Airport to Chicago ticket.

  • Save time looking for cheap flights from OAJ to Chicago by setting up a Price Alert. We'll send you an email or push notification on the app when a special offer becomes available.

  • Select your ideal arrival and departure times, airlines and number of stops with our filters. Then, sort the results for your flight from Albert J Ellis Airport to Chicago by 'Fastest,' 'Cheapest' or 'Best.'

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • The distance from Chicago O'Hare International Airport (ORD) to central Chicago is roughly 27 kilometres. It takes around 30 minutes to get to the centre driving.

  • It'll take around 45 minutes to get there using public transport.

  • Think about booking a hotel near ORD if you're coming in on a late flight from Albert J Ellis Airport to Chicago. Check in to one of these options and make arrival day easier:

  • Lock in the best deal by booking your vehicle from Chicago O'Hare International Airport around four weeks before your flight from OAJ to Chicago.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is roughly 16 kilometres from the centre of Chicago. Once you've hopped off your flight from Albert J Ellis Airport to Chicago, it'll take you around 25 minutes to reach the heart of the city in a ride-share or taxi.

  • You can expect the trip to take about 30 minutes on public transport.

  • You'll find some great places to park your luggage (and yourself) near MDW. Settle in and get cosy after your OAJ to Chicago flight at one of these well-located options:

  • Lock in the lowest price by securing your ride from MDW four weeks ahead of time. You'll also have access to a greater selection of vehicles.

  • Chicago Midway International Airport can be found at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is around 145 kilometres from the centre of Chicago. It takes about 1 hour 40 minutes to reach the city centre by car after your flight from Albert J Ellis Airport to Chicago.

  • The journey will take you about 2 hours when travelling on public transport.

  • If you don't want to make the journey to the centre, find a hotel close to RFD. Check in to one of these options after your OAJ to Chicago flight:

  • Booking a couple of weeks in advance of your flight from Albert J Ellis Airport to Chicago is always smart. Along with better deals, you might find it easier to get the make and model you prefer at RFD.

  • Chicago Rockford International Airport's official address is 2 Airport Cir.

Best time to go to Chicago

  • It's time to plan your dates for your flight from Albert J Ellis Airport to Chicago. July is the busiest month to visit Chicago. If you like a more low-key vibe, go in January.

  • The warmest month in Chicago is July, with temperatures ranging between 16ºC (61ºF) and 28ºC (82ºF). Book your Albert J Ellis Airport to Chicago plane ticket then if this is the type of weather you enjoy.

  • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for a cheap ticket from OAJ to Chicago around that time if you like cooler conditions.

More about Chicago

Explore more of the United States

  • Chicago is always a good idea, but there are so many other parts of the United States waiting to be explored. Around 451 kilometres southeast of Chicago, a visit to Columbus will fill your itinerary to the brim. Start with leading attractions like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • Around 257 kilometres southeast of Chicago, Indianapolis is another favourite stop in the United States. Experience the best of this destination with a visit to Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.