$168 Flights from Jacksonville (OAJ) to Chicago (CHIA)

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Flight deals from Jacksonville Airport to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Jacksonville Airport to Chicago? If you want to travel next month, round-trip fares start from $446. Find the lowest prices on one-way and round-trip 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 April.

Jacksonville to Chicago: Flight information

The things to know before you go.
Cheapest flight found$168
Cheapest month to flyApril

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 round-trip flight from Jacksonville to Chicago is $377. 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 $377.
There are no flights flying from Jacksonville to Chicago, as of January 2026.
The cheapest month to fly from Jacksonville to Chicago is usually June.
If you're flying from Jacksonville Airport, the cheapest airport near Chicago is Chicago Midway – which is 9.0 miles away from the center of Chicago. We've found flights to this airport from $377.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Jacksonville Airport to Chicago on Monday, June 1, 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 January, the average temperature is usually around 24°F. July is typically the warmest month in Chicago, when it usually averages around 80°F. You can expect the least rain in January. The coldest month is January, with temperatures averaging 18°F. The rainiest month is August.
Currently, Delta offers the cheapest flight tickets to Chicago.

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

  • The timezone in Chicago is UTC-5. The city is one hour behind Jacksonville, where Albert J Ellis Airport is located.

  • For hassle-free travel, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This will give you plenty of time to board your OAJ to Chicago flight.

  • Heading away during a peak period like school or public holidays? Expect longer lines at security and check-in. For peace of mind, arrive up to four hours before international flights and two hours before domestic departures.

  • OAJ is about 11 miles from central Jacksonville. If you're driving, catching a cab or ride-sharing from the center, it'll take you 20 minutes or so to get there, depending on the traffic.

  • Albert J Ellis Airport maintains a solid on-time performance, so flight disruptions are less likely. Departures from OAJ land at their destination as scheduled 83.69% of the time.

  • The address for OAJ is 264 State Road 1265.

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

  • $168 is currently the best price for a one-way Albert J Ellis Airport to Chicago flight. Return plane tickets start from $377. These fares can change depending on availability and demand.

  • Don't leave everything to the last moment. You're more likely to find cheap flights from OAJ to Chicago if you book early. Airlines often have some amazing early bird deals.

  • Landing cheap tickets from Albert J Ellis Airport to Chicago is more likely if you can be flexible with your travel plans. Use the 'Whole month' search function to access the best prices across the month and score an awesome deal.

  • You don't need to check in daily to find out if fares have dropped when you set up a Price Alert. We'll let you know as soon as there's an even better deal on cheap flights from OAJ to Chicago.

  • Tailor your trip with filters. Select your ideal arrival and departure times, airlines and total journey duration. You can also sort the results by 'Best,' 'Cheapest' or 'Fastest' flights from Albert J Ellis Airport to Chicago.

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 25 miles. It takes around 35 minutes to get to the center driving.

  • Traveling by public transport typically takes 55 minutes.

  • The last thing you need is a lengthy journey to your hotel if you're arriving on a late flight from Albert J Ellis Airport to Chicago. Reserve one of these accommodation options near ORD instead:

  • Hit the road running by picking up an O'Hare International Airport rental car. Grab your wheels from Routes Car Rentals, Dollar or Budget and experience the lesser-explored corners of Chicago and beyond.

  • Get the best deal by reserving your vehicle from O'Hare International Airport about four weeks in advance of your flight from OAJ to Chicago.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • The center of Chicago is around 12 miles from Chicago Midway International Airport (MDW). Once your flight from Albert J Ellis Airport to Chicago has hit the runway and you've made your way through the terminal, expect a drive of around 20 minutes.

  • You can expect the trip to take about 45 minutes on public transport.

  • Hang the 'Do not disturb' sign on your door and relax at a hotel close to MDW. Here are a few options where you can tuck yourself in after your OAJ to Chicago flight:

  • The quickest way to reach your destination is with a Chicago Midway International Airport rental car. Collect your wheels from Dollar, Hertz or Budget and get going in the blink of an eye.

  • Avoid paying more than you need to. Booking your ride four weeks before your arrival at MDW can help you lock in a better rate.

  • You can find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Head to the city center after your flight from Albert J Ellis Airport to Chicago has arrived. Central Chicago is around 85 miles from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 25 minutes to get to by car.

  • The journey will take roughly 4 hours 15 minutes when traveling on public transport.

  • Enjoy a quiet, low-key start to your trip by choosing a hotel near RFD after your OAJ to Chicago flight. Unwind after a day of travel or simply give yourself time to get your bearings in a new city at:

  • Begin your journey without stressing over how to get to your next stop with a Chicago Rockford International Airport rental car. Book your ideal wheels with reliable companies here like Budget, Alamo and National.

  • Rental providers sometimes offer promotions for early bookings, so reserve your ride from RFD in advance of your flight from Albert J Ellis Airport to Chicago. A bit of planning goes a long way in savings.

  • The address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Plan your trip to Chicago in peak season if you want a bustling atmosphere, but remember that hotel prices tend to be higher. Alternatively, book flights from Albert J Ellis Airport to Chicago during low season when prices are cheaper and it's quieter.

  • The warmest month in Chicago is July, with temperatures ranging between 59ºF and 84ºF. Book your Albert J Ellis Airport to Chicago plane ticket then if that's your idea of comfortable weather.

  • Look for cheap tickets from OAJ to Chicago in January if you'd rather travel when it's cooler. Temperatures are at their lowest then, ranging between 10ºF and 37ºF on average.

More about Chicago

Explore more of United States

  • You've visited Chicago, now it's time to explore more of United States. Journey about 280 miles south-east to Columbus to tick off its popular sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, there's plenty to keep you busy.

  • If you're eager to discover another major destination in United States, head for Indianapolis, roughly 160 miles south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are highlights.

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