ORD - OAJ

$129 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 8/25. 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.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Jacksonville

 
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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Flights Deals

Cheap Flights from Chicago to Jacksonville (ORD-OAJ)

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Jacksonville

Sun, Sep 7 - Sat, Sep 13
American Airlines Logo
7:02 am - 1:35 pmORD-OAJ
5h 33m1 stop
American Airlines Logo
5:22 pm - 11:12 pmOAJ-ORD
6h 50m1 stop
$257American Airlines
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Tue, Aug 26 - Tue, Sep 2
American Airlines Logo
7:35 am - 2:55 pmORD-OAJ
6h 20m1 stop
American Airlines Logo
7:17 pm - 10:59 pmOAJ-ORD
4h 42m1 stop
$258American Airlines
Find Deal
Tue, Aug 12 - Tue, Aug 19
American Airlines Logo
11:45 am - 6:46 pmORD-OAJ
6h 01m2 stops
American Airlines Logo
7:17 pm - 10:59 pmOAJ-ORD
4h 42m1 stop
$262American Airlines
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Wed, Sep 10 - Sun, Sep 14
American Airlines Logo
8:38 am - 1:56 pmORD-OAJ
4h 18m1 stop
American Airlines Logo
8:02 pm - 11:39 pmOAJ-ORD
4h 37m1 stop
$268American Airlines
Find Deal
Tue, Aug 26 - Tue, Sep 2
American Airlines Logo
11:45 am - 6:46 pmORD-OAJ
6h 01m2 stops
American Airlines Logo
7:17 pm - 10:59 pmOAJ-ORD
4h 42m1 stop
$305American Airlines
Find Deal
Wed, Sep 10 - Sun, Sep 14
American Airlines Logo
1:37 pm - 9:06 pmORD-OAJ
6h 29m2 stops
American Airlines Logo
8:02 pm - 11:39 pmOAJ-ORD
4h 37m1 stop
$314American Airlines
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Sun, Sep 7 - Sat, Sep 13
Delta Logo
5:45 am - 11:10 amORD-OAJ
4h 25m1 stop
Delta Logo
5:52 am - 10:08 amOAJ-ORD
5h 16m1 stop
$322Delta
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Sat, Sep 27 - Tue, Sep 30
American Airlines Logo
5:00 am - 11:06 amORD-OAJ
5h 06m1 stop
American Airlines Logo
7:10 pm - 11:12 pmOAJ-ORD
5h 02m1 stop
$339American Airlines
Find Deal
Sat, Sep 27 - Tue, Sep 30
American Airlines Logo
1:37 pm - 9:06 pmORD-OAJ
6h 29m2 stops
American Airlines Logo
7:10 pm - 11:12 pmOAJ-ORD
5h 02m1 stop
$344American Airlines
Find Deal
Fri, Oct 10 - Tue, Oct 14
Delta Logo
6:00 am - 1:40 pmORD-OAJ
6h 40m1 stop
Delta Logo
5:40 am - 10:03 amOAJ-ORD
5h 23m1 stop
$468Delta
Find Deal
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KAYAK's insights & trends for Chicago to Jacksonville flights

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.

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

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Jacksonville clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Jacksonville on a Wednesday and more expensive on a Saturday. On your return trip to Chicago, you should consider flying back on a Saturday, and avoid Fridays for better deals.

Good to know

Cheapest flight$129
Flight from Chicago 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 Chicago to Jacksonville flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Jacksonville?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Jacksonville was $129 for a one-way ticket and $257 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 aircraft models fly most regularly from Chicago to Jacksonville?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Jacksonville?

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Jacksonville are Delta and American Airlines. With an average price for the route of $356 and an overall rating of 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $416 and an overall rating of 7.2.

  • 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. Booking your flights between Chicago and OAJ can sometimes prove cheaper using this method.

  • 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.

Reviews of the top airlines flying 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.
8.0
DeltaOverall score based on 7950 reviews
8.2Boarding
7.9Entertainment
7.3Food
7.9Comfort
8.5Crew
Airline reviews

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

4.0 OkayJames, Jul 2025MSN - ATL
Read more Delta reviews

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this 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.

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.

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

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