CHI - JAX

$79 Find Cheap Flights from Chicago to Jacksonville

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Jacksonville departing on 5/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Jacksonville, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Jacksonville, as well as popular online travel agencies
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Cheap Flight Deals from Chicago to Jacksonville (CHI-JAX)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Jacksonville that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Jacksonville

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Jacksonville.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:47 am - 9:46 amMDW-JAX
23h 59m2 stops
8:43 am - 12:17 amJAX-MDW
40h 34m2 stops
$184Frontier
Find Deal
Tue, Mar 4 - Tue, Mar 11
6:20 am - 9:46 amORD-JAX
26h 26m2 stops
8:43 am - 10:57 amJAX-ORD
27h 14m2 stops
$190Frontier
Find Deal
Tue, Mar 4 - Tue, Mar 11
5:35 pm - 8:59 pmORD-JAX
2h 24mnonstop
12:11 pm - 1:51 pmJAX-ORD
2h 40mnonstop
$196American Airlines
Find Deal
Tue, Mar 4 - Tue, Mar 11
6:06 pm - 9:34 pmORD-JAX
2h 28mnonstop
3:07 pm - 4:56 pmJAX-ORD
2h 49mnonstop
$197United Airlines
Find Deal
Tue, Mar 4 - Tue, Mar 11
12:45 pm - 4:00 pmMDW-JAX
2h 15mnonstop
7:40 am - 9:10 amJAX-MDW
2h 30mnonstop
$197Southwest
Find Deal
Tue, Mar 4 - Tue, Mar 11
11:15 am - 8:05 pmORD-JAX
7h 50m1 stop
8:05 am - 9:52 amJAX-ORD
2h 47mnonstop
$207United Airlines
Find Deal
Tue, Mar 4 - Tue, Mar 11
10:30 am - 5:10 pmMDW-JAX
5h 40m1 stop
7:40 am - 9:10 amJAX-MDW
2h 30mnonstop
$207Southwest
Find Deal
Tue, Mar 4 - Tue, Mar 11
9:38 am - 2:57 pmORD-JAX
4h 19m1 stop
12:11 pm - 6:21 pmJAX-ORD
7h 10m1 stop
$217Delta
Find Deal
Tue, Mar 4 - Tue, Mar 11
10:25 am - 5:40 pmMDW-JAX
6h 15m1 stop
5:35 am - 9:09 amJAX-MDW
4h 34m1 stop
$217Delta
Find Deal
Tue, Mar 11 - Tue, Mar 18
11:53 am - 6:02 pmORD-JAX
5h 09m1 stop
5:42 am - 7:22 amJAX-ORD
2h 40mnonstop
$226American Airlines
Find Deal
Tue, Mar 4 - Tue, Mar 11

Flights from Chicago to Jacksonville - Travel Insights & Trends

Get data-powered insights and trends into flights from Chicago to Jacksonville to help you find the cheapest flights, the best time to fly and much more.
Find cheap flights to Jacksonville
Find cheap flights to Jacksonville

Planning a trip from Chicago to Jacksonville? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.

What is the cheapest Chicago to Jacksonville flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Jacksonville.
Our data shows that the cheapest route for a return flight from Chicago to Jacksonville cost $217 and was between Chicago Midway Airport (MDW) and Jacksonville (JAX). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $217.

What’s the cheapest day of the week to fly from Chicago to Jacksonville?

The average price of all round-trip flights from Chicago to Jacksonville clicked on KAYAK for each day over the last 12 months.
For Chicago to Jacksonville, Wednesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Jacksonville back to Chicago, the best deals are generally found on Thursday, with Sunday being the most expensive.

What is the cheapest month to fly from Chicago to Jacksonville?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Jacksonville, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago to Jacksonville is September, where tickets cost $313 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $429 and $416 respectively.

How far in advance should I book a flight from Chicago to Jacksonville?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Jacksonville, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.
To get a below average price on the flight from Chicago to Jacksonville, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low season

January

High season

March

Cheapest flight

$79
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 13% increase in price.
Flight from Chicago Midway Airport to Jacksonville

When to book flights from Chicago to Jacksonville

Are your dates flexible? Find out the best times to travel from Chicago to Jacksonville based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Jacksonville

  • Are there hotels near O’Hare International Airport (ORD)?

    The Rose Chicago, Tapestry Collection by Hilton and Holiday Inn Express & Suites - Chicago O'Hare Airport, An IHG Hotel are the most convenient hotels for those who wish to book a room near the O’Hare International Airport (ORD). The hotels are located 1.7 miles and 1.6 miles away from the airport. The Rose Hotel is pet friendly and has a fitness center for its customers to use.

  • What types of flights are available from O’Hare International Airport (ORD) to Jacksonville Airport (JAX)?

    There are both direct and connecting flights between the destinations. American Airlines and United Airlines offer direct flights from O’Hare International Airport (ORD) to Jacksonville Airport (JAX). However, American Airlines also offers flights with a layover at Charlotte Douglas International Airport (CLT).

  • Are there lounges in O’Hare International Airport (ORD)?

    There are a couple of lounges within the different terminals within the airport. Terminal 1 is equipped with 4 United Club lounges at different locations: near Gates B6, B18, C16, and C18. Terminal 2 hosts both the United Club and the Delta Sky Club. Terminal 3 is mainly occupied by the Admirals Club by American Airlines in the different locations, near Gates G8 and Gate L1, between gates H6 and K6, and lastly is the Flagship Lounge. Terminal 5, which is the International Terminal, has also a couple of lounges.

  • What is the most convenient way to get to downtown Jacksonville from Jacksonville Airport (JAX)?

    The Line 1 bus is the most convenient means of public transport from the airport to downtown Jacksonville. It will only take you an hour to complete the journey whereas a taxi from the airport would take 18min to complete the journey.

  • What is the cheapest flight from Chicago to Jacksonville?

    In the last 3 days, the lowest price for a flight from Chicago to Jacksonville was $79 for a one-way ticket and $184 for a round-trip.

  • Do I need a passport to fly between Chicago and Jacksonville?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Chicago to Jacksonville?

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at Jacksonville.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Jacksonville?

    American Airlines, and Delta offer inflight Wi-Fi service on the Chicago to Jacksonville flight route.

  • Which aircraft models fly most regularly from Chicago to Jacksonville?

    The Embraer 170 is the aircraft model that flies most regularly on the Chicago to Jacksonville flight route.

  • Which airline alliances offer flights from Chicago to Jacksonville?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Jacksonville, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Jacksonville?

    There are nonstop flights from Chicago to Jacksonville on a daily basis.

  • Which is the best airline for flights from Chicago to Jacksonville, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Jacksonville are Southwest and Delta. With an average price for the route of $380 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $307 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Chicago to Jacksonville?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Jacksonville.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Jacksonville?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Jacksonville from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Jacksonville?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Jacksonville with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Jacksonville?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Jacksonville from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Chicago to Jacksonville

  • Looking for a cheap flight? 25% of our users found flights on this route for $198 or less one-way and $316 or less round-trip.
  • Chicago is served by two international airports, the O’Hare International Airport (ORD) and the Midway International Airport (MDW). Although the O’Hare International Airport (ORD) is considered the main airport of the two, the Midway International Airport (MDW) is closer to downtown Chicago as compared to O’Hare International (ORD) which are 12.5 miles and 18 miles away respectively.
  • Home2 Suites by Hilton Jacksonville Airport and the Hampton Inn & Suites Jacksonville-Airport hotels are the most convenient hotels to book a room if you have arrived late at the Jacksonville Airport (JAX). The hotels are located 2.2 miles and 1.9 miles away respectively from the airport.
  • There are two pet relief areas in Jacksonville International Airport (JAX), one is located outside the airport before the security while the other is found inside the terminal past the security. The Indoor Pet Relief Area is located between Concourse C and A whereas the outdoor area is located on the south side of the terminal outside the baggage claim area.
  • There are six pet relief areas within O’Hare International Airport (ORD). Two of these areas are located inside airport security and four of them are in the outdoor areas.
  • Jacksonville International Airport (JAX) has a nursing room past the security between Concourse C and A. The suite has a table and a power outlet. These suites offer a combination of comfort and privacy when it comes to accommodating nursing mothers within the airport.
See more tips

Prefer to fly direct from Chicago to Jacksonville?

Find which airlines fly direct from Chicago to Jacksonville Airport, which days they fly and book direct flights.

Direct departures

Chicago to Jacksonville

Monday

ANA, Air Canada, Air New Zealand, +8 more

ANA, Air Canada, +9 more

Tuesday

ANA, Air Canada, Air New Zealand, +8 more

ANA, Air Canada, +9 more

Wednesday

ANA, Air Canada, Air New Zealand, +8 more

ANA, Air Canada, +9 more

Thursday

ANA, Air Canada, Air New Zealand, +8 more

ANA, Air Canada, +9 more

Friday

ANA, Air Canada, Air New Zealand, +8 more

ANA, Air Canada, +9 more

Saturday

ANA, Air Canada, Air New Zealand, +8 more

ANA, Air Canada, +9 more

Sunday

ANA, Air Canada, Air New Zealand, +8 more

ANA, Air Canada, +9 more

See more direct flights

Direct returns

Jacksonville to Chicago

Monday

ANA, Air Canada, Air New Zealand, +8 more

ANA, Air Canada, +9 more

Tuesday

ANA, Air Canada, Air New Zealand, +8 more

ANA, Air Canada, +9 more

Wednesday

ANA, Air Canada, Air New Zealand, +8 more

ANA, Air Canada, +9 more

Thursday

ANA, Air Canada, Air New Zealand, +8 more

ANA, Air Canada, +9 more

Friday

ANA, Air Canada, Air New Zealand, +8 more

ANA, Air Canada, +9 more

Saturday

ANA, Air Canada, Air New Zealand, +8 more

ANA, Air Canada, +9 more

Sunday

ANA, Air Canada, Air New Zealand, +8 more

ANA, Air Canada, +9 more

See more direct flights
See more direct flights

Top 5 airlines serving from Chicago to Jacksonville

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Jacksonville. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Jacksonville? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.1
SouthwestOverall score based on 4553 reviews
8.7Crew
7.1Food
8.1Comfort
8.2Boarding
7.7Entertainment
Airline reviews

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

10.0 ExcellentKeith, Jan 2025IND - MCO
Read more Southwest reviews

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

It went well. Plane wasn't full. Will be great when assigned seating is in place

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

Pretty standard flight. We left late, but arrived early. The wifi entertainment is always nice. The free snacks and beverages are simple, but appreciated. I'm tall and the seats are an issue. I can deal with a short flight, but any longer, I have to find another airline where I know beforehand I have extra legroom.

The flight attendant was proactive in helping with placing carry on in overhead bins. This was the first time I had ever been offered help without asking or obviously struggling. Many on the flight were older people like myself and vertically challenged. I would hope this would be the norm on all flights.

wifi wasn't working correctly so couldn't watch live tv

Flight was delayed by 12 minutes. Boarding wasn’t fun. The crew was nice though.

The flight was promptly on schedule and Southwest delivered everything they promised. No excuses for any shortfalls just 100% ownership of their responsibilities and business. The boarding and seating policy is a complete shambles. What started out as a great idea when Southwest first hit the market has been turned into a disaster due to the lack of integrity in many of the people who fly Southwest and take advantage of Southwest generosity at the expense of their fellow passengers.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

Loyal Delta traveler, but last nights flight was a train wreck. Seated in 1B after multiple delays. Then we couldn’t takeoff because of an issue with the passenger that was ‘not in compliance’ and had to deplane along with the threat if they did not deplane, all the passengers would be required to do so. Finally they were escorted off, but the experience threw off the crew. Disruptive for everyone. Service was a mess, televisions didn’t work, bathroom door kept swinging open during the entire flight whenever empty …

My flight was cancelled twice and the third time I tried to rebook it online I cancelled the flight because it looked like I would get a refund to my credit card. Instead I now have a credit. I was also on hold for three hours waiting for a representative and then disconnected. I will never fly delta again.

It was very cold because the air conditioner was on high power, and my son got sick.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

The flying experience was great. The flight was on time with no boarding issues during a peak travel period. The short cut baggage drop and process was not smooth and efficient at Dulles.

Plane was was better than th YVR to ORD flight but was a fraction of the distance. Fly your better planes on longer distance flights.

Nothing wrong with the flight itself. But due to 2+ hrs waiting in immigration and the additional security checkup in O’hare, I nearly missed the flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

I had a very unpleasant encounter with one man from customer service: he was extremely rude and miserable. And his condition was reflected on his decision to send me to the worst airport hotel and get an awful flight connection. My hotel shuttle had never arrived and I had to book another hotel. People served by other representatives got a much better treatment and deal.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

Check in at Philadelphia international was absolutely terrible! I fly 2 to 3 times a month and avoid frontier at all cost and will never fly Frontier again! The night before travel, I tried checking in however, the app was giving me an error, so I went to the desktop, which instructed you that you need to use the app. The next day I presented at the check-in gate after trying at least a half dozen times prior to getting into the airport and continuing to getting the error in the app. I actually had rebooted my phone numerous times and reinstall the app just in case. My phone is only one generation older than the current model. It has no problems completing a frontier flight purchase or any other app issues. There was only three frontier employees working at check-in and a huge line while I was in line I continued to try and check in via the app. As I approach the desk, I was dreading dealing with the agent. He was extremely unprofessional, anti-semantic & very ignorant, and mean to the people in front of me, as well as the people who ended up being behind me. He literally told people “Man I don’t care bout y’all” in his native dialect! Maintaining my composure I approached and explained the situation. To which he replied, you’re gonna have to pay then! I don’t understand. It’s an issue with their app not allowing me to check in! Not my issue! He told me if I pay cash it would be $15, $25 if I pay credit card. I don’t understand a $10 difference for paying with a credit card? I am completely cashless so I continued to try using the app to avoid the $25 fee, Which I still don’t believe that I should be responsible for since it was Frontier’s technical issue!!! I continued to check in via the app a couple more times after he verified I was doing everything right he proceeded to continue to belittle the people behind me. Yelling at them saying I don’t care about you people! I cannot believe that this is the way that businesses would treat its customers! Unfortunately, the black mail with dreadlocks did not have a name tag all he had was a frontier sweater on! For the $25 fee that I ended up getting charged on my credit card. I should’ve just booked originally with Spirit or any other carrier! I have no problem paying fees that I should be responsible for, but when it’s due to a technical failure of a company, the customer should not be responsible for it! I cannot believe that it’s not frontier going out of business!

they delayed my flight which ended up, causing my layover flight to leave without me, resulting in me missing a flight and having to stay overnight in Houston international. I got no compensation other than a flight to my original location only a day later. i’ve never experienced such a unprofessional situation

Our flight was suppose to leave at 9pm and we didn’t board until after 3am. We lost a whole day at our hotel and half a day at a park we paid a lot of money for.

Boarding was organized and flight was on time. Overall very satisfied with my flight.

The boarding gate was in Terminal D, but the Frontier counter was in Terminal E. So I had to move back and forth between terminals to check in my luggage. This was the worst experience that I had in terms of flights.

Booked direct in July '24. Turned into a 14 hr layover (both ways) in Denver. My 5 day vaca turned into a 1 day . Not good, BUT,... Thank you for the people @ Frontier who were professionally friendly & approachable.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

Airline changed the gate from Terminal A to Terminal D which is quite far and only sent a text message few minutes before boarding. Around 50 people missed their flight and as plane didn’t wait for them.

The personal at boarding are rude and try to steel people with their rule of personal item , really bad experience for us

I did not like that people are purposely split ip who book at the same time because we didn’t buy seats. No other airline does that.

Everything you need to know for your flight from Chicago to Jacksonville

Information on your arrival and departure airports

Compare transportation modes for Chicago to Jacksonville

Average priceAverage duration
Flights$3192h 15m
Trains$2300h 00m

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