ORD - OAJ

$182 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 8/15. 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

Fri, Aug 1 - Fri, Aug 8
American Airlines Logo
7:05 am - 12:57 pmORD-OAJ
4h 52m1 stop
American Airlines Logo
6:10 am - 9:44 amOAJ-ORD
4h 34m1 stop
$387American Airlines
Find Deal
Tue, Jul 22 - Tue, Jul 22
Delta Logo
7:00 am - 2:46 pmORD-OAJ
6h 46m1 stop
Delta Logo
7:14 pm - 12:09 amOAJ-ORD
5h 55m1 stop
$435Delta
Find Deal
Thu, Jul 17 - Mon, Jul 21
American Airlines Logo
7:05 am - 2:22 pmORD-OAJ
6h 17m1 stop
American Airlines Logo
6:04 pm - 9:31 pmOAJ-ORD
4h 27m1 stop
$447American Airlines
Find Deal
Fri, Aug 1 - Fri, Aug 8
American Airlines Logo
9:17 am - 2:22 pmORD-OAJ
4h 05m1 stop
American Airlines Logo
6:10 am - 11:51 amOAJ-ORD
6h 41m2 stops
$644American Airlines
Find Deal
Thu, Jul 17 - Mon, Jul 21
American Airlines Logo
7:05 am - 12:57 pmORD-OAJ
4h 52m1 stop
American Airlines Logo
2:47 pm - 7:45 pmOAJ-ORD
5h 58m2 stops
$704American Airlines
Find Deal
Tue, Jul 22 - Tue, Jul 22
Delta Logo
7:10 am - 2:46 pmORD-OAJ
6h 36m2 stops
Delta Logo
7:14 pm - 12:09 amOAJ-ORD
5h 55m1 stop
$867Delta
Find Deal
Thu, Jul 17 - Mon, Jul 21
American Airlines Logo
6:51 am - 2:22 pmORD-OAJ
6h 31m2 stops
American Airlines Logo
2:47 pm - 7:45 pmOAJ-ORD
5h 58m2 stops
$892American Airlines
Find Deal
Fri, Aug 1 - Fri, Aug 8
Delta Logo
9:00 am - 10:16 pmORD-OAJ
12h 16m2 stops
Delta Logo
11:54 am - 8:24 pmOAJ-ORD
9h 30m2 stops
$1,195Delta
Find Deal
Fri, Aug 1 - Fri, Aug 8
Delta Logo
11:01 am - 10:16 pmORD-OAJ
10h 15m2 stops
Delta Logo
11:54 am - 8:24 pmOAJ-ORD
9h 30m2 stops
$1,396Delta
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

Low seasonSeptember
High seasonSeptember
Cheapest flight$182
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly and prices are also 34% lower on average.
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 $182 for a one-way ticket and $387 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?

    oneworld, and SkyTeam 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 7983 reviews
7.9Entertainment
7.9Comfort
8.5Crew
8.2Boarding
7.3Food
Airline reviews

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

4.0 OkayAnonymous, Jul 2025HSV - ATL
Read more Delta reviews

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.

From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Only not having an assigned seat was an issue. Rest was great

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.

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..

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

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