Cheap Flights from Jacksonville International to Chicago from $345

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Flight deals from Jacksonville International to Chicago

Looking for a cheap last-minute deal or the best return flight from Jacksonville International Airport to Chicago? If you want to travel next month, return fares start from $345. Find the lowest prices on one-way and return tickets right here.

Chicago.$345 per passenger.Departing Wed, 30 Sep, returning Sat, 3 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Jacksonville International on Wed, 30 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 3 Oct, arriving in Jacksonville International.Price includes taxes and charges.From $345, select.

Chicago.$345 per passenger.Departing Wed, 7 Oct, returning Wed, 21 Oct.Return flight with United.Outbound direct flight with United departs from Jacksonville International on Wed, 7 Oct, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Wed, 21 Oct, arriving in Jacksonville International.Price includes taxes and charges.From $345, select.

Chicago.$345 per passenger.Departing Sat, 22 Aug, returning Sat, 29 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Jacksonville International on Sat, 22 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 29 Aug, arriving in Jacksonville International.Price includes taxes and charges.From $345, select.

Chicago.$346 per passenger.Departing Wed, 9 Sep, returning Sat, 12 Sep.Return flight with United.Outbound direct flight with United departs from Jacksonville International on Wed, 9 Sep, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 12 Sep, arriving in Jacksonville International.Price includes taxes and charges.From $346, select.

Chicago.$379 per passenger.Departing Sat, 25 Jul, returning Tue, 28 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Jacksonville International on Sat, 25 Jul, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 28 Jul, arriving in Jacksonville International.Price includes taxes and charges.From $379, select.

Chicago.$398 per passenger.Departing Fri, 31 Jul, returning Tue, 4 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Jacksonville International on Fri, 31 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 4 Aug, arriving in Jacksonville International.Price includes taxes and charges.From $398, select.

Chicago.$432 per passenger.Departing Thu, 5 Nov, returning Tue, 10 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Jacksonville International on Thu, 5 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 10 Nov, arriving in Jacksonville International.Price includes taxes and charges.From $432, select.

Chicago.$473 per passenger.Departing Fri, 31 Jul, returning Tue, 4 Aug.Return flight with United.Outbound direct flight with United departs from Jacksonville International on Fri, 31 Jul, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 4 Aug, arriving in Jacksonville International.Price includes taxes and charges.From $473, select.

Chicago.$516 per passenger.Departing Sat, 5 Dec, returning Mon, 7 Dec.Return flight with United.Outbound direct flight with United departs from Jacksonville International on Sat, 5 Dec, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Mon, 7 Dec, arriving in Jacksonville International.Price includes taxes and charges.From $516, select.

Chicago.$555 per passenger.Departing Sun, 26 Jul, returning Tue, 28 Jul.Return flight with United.Outbound direct flight with United departs from Jacksonville International on Sun, 26 Jul, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 28 Jul, arriving in Jacksonville International.Price includes taxes and charges.From $555, select.

Chicago.$597 per passenger.Departing Fri, 19 Feb, returning Mon, 22 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Jacksonville International on Fri, 19 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 22 Feb, arriving in Jacksonville International.Price includes taxes and charges.From $597, select.

Chicago.$597 per passenger.Departing Wed, 6 Jan, returning Wed, 13 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Jacksonville International on Wed, 6 Jan, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 13 Jan, arriving in Jacksonville International.Price includes taxes and charges.From $597, select.

Chicago.$598 per passenger.Departing Wed, 30 Dec, returning Sat, 2 Jan.Return flight with United.Outbound direct flight with United departs from Jacksonville International on Wed, 30 Dec, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 2 Jan, arriving in Jacksonville International.Price includes taxes and charges.From $598, select.

Chicago.$664 per passenger.Departing Fri, 30 Oct, returning Sun, 1 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Jacksonville International on Fri, 30 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 1 Nov, arriving in Jacksonville International.Price includes taxes and charges.From $664, select.

Chicago.$1,010 per passenger.Departing Tue, 16 Mar, returning Sat, 20 Mar.Return flight with United.Outbound direct flight with United departs from Jacksonville International on Tue, 16 Mar, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 20 Mar, arriving in Jacksonville International.Price includes taxes and charges.From $1,010, select.

Find the cheapest month to fly from Jacksonville International to Chicago

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

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Direct flights from Jacksonville International to Chicago

Alternative Jacksonville International to Chicago routes

Looking for the cheapest, fastest or easiest route from Jacksonville International to Chicago? You could fly into the following airports instead.

Jacksonville to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$345
Cheapest month to fly	August
Average flight time	2 hrs, 41 mins
Most popular airline	American Airlines
Average flights per week	267

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

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.

How much are return flights from Jacksonville International to Chicago?

The best price we found for a return flight from Jacksonville International to Chicago is $345. 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.

How long does it take to fly from Jacksonville International to Chicago?

2 hours and 40 minutes is the average flight time from Jacksonville International to Chicago.

Which airlines fly direct from Jacksonville International to Chicago?

American Airlines, Alaska Airlines and United fly direct from Jacksonville International to Chicago.

How many flights are there a week from Jacksonville International to Chicago?

As of July 2026, there are 267 flights per week flying from Jacksonville International to Chicago.

When is the cheapest time to fly from Jacksonville International to Chicago?

The cheapest month to fly from Jacksonville International to Chicago is usually August.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Jacksonville International Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from $345.

Which upcoming date is cheapest to fly from Jacksonville International Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Jacksonville International Airport to Chicago on Saturday, 22 August 2026.

Can I get a direct flight from Jacksonville International Airport to Chicago?

Yes – the average flight time is 2 hours and 40 minutes.

How can I get the best flight deal from Jacksonville International Airport to Chicago?

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.

When is the best time to book flights to Chicago?

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.

What’s the weather like in Chicago?

In July, the average temperature is usually around 22°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.

Which is the cheapest airline to fly from Jacksonville International Airport to Chicago with?

Currently, Southwest Airlines offers the cheapest flight tickets to Chicago.

Flying from Jacksonville International Airport (JAX) to Chicago: what you need to know

Around 2 hours 25 minutes is how long you can expect to be travelling on a direct flight from Jacksonville International Airport to Chicago.
Jacksonville International Airport is located in Jacksonville. Following the UTC-6 timezone, Chicago is one hour behind Jacksonville.
The busiest route is from Jacksonville International Airport (JAX) to Chicago O'Hare International Airport (ORD). Choose from 39 weekly services between these two airports. If you'd like to take off as soon as possible, the earliest flight from JAX to ORD is the 05:00 American Airlines option. If you prefer travelling later, the last departure is at 16:50 with United Airlines.
Leave enough time to get on your JAX to Chicago flight. A good rule of thumb is to arrive at least two hours before international departures and an hour ahead for domestic flights.
Travelling during a popular month like May? Major public holidays and other popular seasons can lead to longer lines and delays at security. Play things extra safe and get there up to four hours ahead of an international flight and two hours before domestic departures.
Start your trip at JAX and travel straight to Chicago O'Hare International Airport (ORD). That's where you can expect to touch down when searching for Jacksonville International Airport to Chicago tickets.
You'll find a good selection of airlines that offer direct flights from Jacksonville International Airport to Chicago, including:
The journey from central Jacksonville to JAX takes about 1 hour 15 minutes on public transport. If you drive, ride-share or get a taxi, you'll cover the 18 kilometres in 25 minutes or so, depending on traffic conditions.
Searching for a hotel close to JAX? If you've booked an early flight from Jacksonville International Airport to Chicago, these stays will put you moments from your departure gate:
81% of flights leaving Jacksonville International Airport arrive at their destination on schedule. Given its strong performance rating, you're unlikely to face delays when jetting out of JAX.
You'll find JAX at 2400 Yankee Clipper Drive.

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

$172 is currently the lowest price for a one-way Jacksonville International Airport to Chicago flight. A return plane ticket starts from $345. These fares may change depending on demand and availability.
Book three months before flying. Research on pricing trends suggests this is the ideal window for finding cheap flights from JAX to Chicago.
Organise your trip for August. That's the best month for scoring the biggest deals on Jacksonville International Airport to Chicago tickets. If you're open to different travel dates, use the 'Whole month' tool to access the cheapest price across every month.
Save time searching for cheap flights from JAX to Chicago by setting up a Price Alert. You'll get an email or notification through the app when a new discounted fare appears.
Select your preferred departure and arrival times, number of stops and airlines with our filters. Then, sort the results for your flight from Jacksonville International Airport to Chicago by 'Best,' 'Fastest' or 'Cheapest.'

Airports in Chicago

Chicago O'Hare International Airport (ORD)

Chicago O'Hare International Airport (ORD) to central Chicago takes around 30 minutes by car. The centre is roughly 27 kilometres away.
It typically takes 45 minutes to get there using public transport.
Consider staying in a hotel close to ORD if you're coming in on a late flight from Jacksonville International Airport to Chicago. Choose one of these accommodation options and make your first night all about catching up on rest:
Lock in the best rate by booking your vehicle from Chicago O'Hare International Airport about four weeks ahead of your flight from JAX to Chicago.
ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

Central Chicago is around 16 kilometres from Chicago Midway International Airport (MDW). After your flight from Jacksonville International Airport to Chicago has touched down and you've made your way through the terminal, the drive should take about 25 minutes.
The trip will take roughly 30 minutes on public transport.
Hang the 'Do not disturb' sign on your door and relax at a hotel near MDW. Here are a few options where you can tuck yourself in after your JAX to Chicago flight:
Avoid paying extra. Reserving your ride four weeks before your arrival at MDW will save you money.
You'll find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Chicago Rockford International Airport (RFD) is about 145 kilometres from the centre of Chicago. It takes about 1 hour 40 minutes to reach the city centre in a ride-share or taxi once you've stepped off your flight from Jacksonville International Airport to Chicago.
The journey takes roughly 2 hours if you use public transport.
Enjoy an unhurried start to your break by choosing a hotel near RFD after your JAX to Chicago flight. Recharge after a day of travel or just take a moment to find your footing in a new place at:
If you're looking for a particular model or make, booking early increases your chances of snagging what you want. Reserve your ride from RFD at least a couple of weeks ahead of your flight from Jacksonville International Airport to Chicago.
The address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

January is the quietest month for flights from Jacksonville International Airport to Chicago, while July is the busiest. Find the best time to go to Chicago based on whether you prefer a lively atmosphere or a more laid-back vibe.
Book a Jacksonville International Airport to Chicago plane ticket with a departure in July if you want to explore the city during its warmest month. You can expect temperatures to range from 16ºC to 28ºC.
January sees average temperatures of between -12ºC and 3ºC. Search for a cheap ticket from JAX to Chicago around that time if you like travelling in cooler conditions.

More about Chicago

Start your Chicago trip right by choosing the ideal place to stay. After booking your flight from Jacksonville International Airport to Chicago, check out our range of hotels including:
Art Institute of Chicago and Millennium Park are just a couple of the leading attractions to add to your Chicago itinerary. Keep the adventure rolling by checking out Willis Tower.

Explore more of the United States

Chicago is always a good idea, but there are so many other corners of the United States waiting to be discovered. Around 451 kilometres southeast of Chicago, a trip to Columbus will keep your itinerary busy. Don't miss top attractions like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.
If there's time to check out another major destination in the United States, head for Indianapolis, roughly 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are among its highlights.