ORD - OAJ

$159 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 7/8. 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, 0 bags

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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$347
Delta
Fri 11/13Mon 11/16
ORD - OAJ • 1 stop
Cheapest one-way
$159
Delta
Wed 7/8
ORD - OAJ • 1 stop
Top airlines
Delta
Cheapest • from $347 (round-trip)
American Airlines
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Jacksonville. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Atlanta (ATL)
Cheapest • Avg $399 (round-trip)
Charlotte (CLT)
Shortest trip • 4h 52m (one-way)
Insights
Insights
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Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Jacksonville!
Flight Deals
Booking Insights
Flight 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, Nov 13 - Mon, Nov 16
Delta Logo
3:35 pm - 10:15 pm
ORD
-
OAJ
5h 40m
1 stop
Delta Logo
2:25 pm - 6:32 pm
OAJ
-
ORD
5h 07m
1 stop
$347Delta
Fri, Nov 13 - Mon, Nov 16
Delta Logo
5:30 am - 11:12 am
ORD
-
OAJ
4h 42m
1 stop
Delta Logo
2:25 pm - 10:35 pm
OAJ
-
ORD
9h 10m
2 stops
$352Delta
Thu, Aug 27 - Sun, Aug 30
Delta Logo
9:54 am - 6:07 pm
ORD
-
OAJ
7h 13m
1 stop
Delta Logo
2:27 pm - 6:49 pm
OAJ
-
ORD
5h 22m
1 stop
$371Delta
Thu, Aug 27 - Sun, Aug 30
Delta Logo
6:00 am - 6:07 pm
ORD
-
OAJ
11h 07m
2 stops
Delta Logo
12:10 pm - 4:51 pm
OAJ
-
ORD
5h 41m
1 stop
$376Delta
Fri, Nov 13 - Mon, Nov 16
Delta Logo
6:00 am - 5:44 pm
ORD
-
OAJ
10h 44m
2 stops
Delta Logo
2:25 pm - 10:35 pm
OAJ
-
ORD
9h 10m
2 stops
$381Delta
Fri, Jul 3 - Tue, Jul 7
American Airlines Logo
4:45 pm - 10:16 pm
ORD
-
OAJ
4h 31m
1 stop
American Airlines Logo
6:11 pm - 10:00 pm
OAJ
-
ORD
4h 49m
1 stop
$393American Airlines
Thu, Jul 23 - Mon, Jul 27
American Airlines Logo
6:30 am - 2:32 pm
ORD
-
OAJ
7h 02m
1 stop
American Airlines Logo
1:14 pm - 7:51 pm
OAJ
-
ORD
7h 37m
1 stop
$417American Airlines
Fri, Jul 3 - Tue, Jul 7
Delta Logo
3:22 pm - 10:30 pm
ORD
-
OAJ
6h 08m
1 stop
Delta Logo
12:05 pm - 6:45 pm
OAJ
-
ORD
7h 40m
1 stop
$437Delta
Wed, Jul 15 - Fri, Jul 17
American Airlines Logo
6:30 am - 2:32 pm
ORD
-
OAJ
7h 02m
1 stop
American Airlines Logo
3:07 pm - 7:51 pm
OAJ
-
ORD
5h 44m
1 stop
$450American Airlines
Wed, Jul 8 - Sat, Jul 11
Delta Logo
9:45 am - 3:54 pm
ORD
-
OAJ
5h 09m
1 stop
Delta Logo
4:35 pm - 8:33 pm
OAJ
-
ORD
4h 58m
1 stop
$467Delta
Booking Insights

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.

Which airlines provide the cheapest flights from Chicago to Jacksonville?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Chicago to Jacksonville were found on Delta ($347) and American Airlines ($393).

Find deals

Good to know

Cheapest flight$159
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 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Jacksonville was $159 for a one-way ticket and $347 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 is the only airline alliance operating flights between Chicago and Jacksonville.

  • 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 airline 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.
7.1
American AirlinesOverall score based on 11660 reviews
7.5Boarding
6.8Entertainment
6.4Food
7.9Crew
7.2Comfort
Airline reviews

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

2.0 MediocreGirish, Jun 2026
ORD - DFW
Read more American Airlines reviews

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

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

Information on your arrival and departure airports

Chicago (ORD)
Jacksonville (OAJ)