ORD - OAJ

$165 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 2/14. 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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Everything you should know

Cheapest round-trip
$350
Delta
Sat 2/28Tue 3/3
ORD - OAJ • 1 stop
Cheapest one-way
$181
American Airlines
Sat 2/14
ORD - OAJ • 1 stop
Top airlines
Delta
Cheapest • from $350 (round-trip)
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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

Sat, Feb 28 - Tue, Mar 3
Delta Logo
6:45 am - 2:47 pm
ORD
-
OAJ
7h 02m1 stop
Delta Logo
11:48 am - 4:51 pm
OAJ
-
ORD
6h 03m1 stop
$350Delta
Sat, Feb 14 - Sun, Feb 15
American Airlines Logo
6:48 pm - 11:55 pm
ORD
-
OAJ
4h 07m1 stop
American Airlines Logo
4:11 pm - 7:40 pm
OAJ
-
ORD
4h 29m1 stop
$358American Airlines
Fri, Apr 10 - Wed, Apr 15
Delta Logo
7:05 am - 1:40 pm
ORD
-
OAJ
5h 35m1 stop
Delta Logo
11:58 am - 6:49 pm
OAJ
-
ORD
7h 51m1 stop
$362Delta
Sat, Feb 14 - Sun, Feb 15
American Airlines Logo
11:40 am - 7:26 pm
ORD
-
OAJ
6h 46m2 stops
American Airlines Logo
5:00 am - 9:05 am
OAJ
-
ORD
5h 05m1 stop
$363American Airlines
Thu, Apr 9 - Mon, Apr 13
American Airlines Logo
5:00 am - 10:26 am
ORD
-
OAJ
4h 26m1 stop
American Airlines Logo
7:55 pm - 11:57 pm
OAJ
-
ORD
5h 02m1 stop
$377American Airlines
Fri, Apr 10 - Mon, Apr 13
Delta Logo
7:05 am - 1:40 pm
ORD
-
OAJ
5h 35m1 stop
Delta Logo
2:20 pm - 6:49 pm
OAJ
-
ORD
5h 29m1 stop
$395Delta
Tue, Jan 13 - Sat, Jan 17
Delta Logo
2:50 pm - 9:42 pm
ORD
-
OAJ
5h 52m1 stop
Delta Logo
11:44 am - 4:44 pm
OAJ
-
ORD
6h 00m1 stop
$441Delta
Tue, Jan 13 - Sat, Jan 17
American Airlines Logo
6:05 am - 11:11 am
ORD
-
OAJ
4h 06m1 stop
American Airlines Logo
3:25 pm - 10:34 pm
OAJ
-
ORD
8h 09m2 stops
$486American Airlines
Wed, Mar 25 - Mon, Mar 30
Delta Logo
9:50 am - 6:08 pm
ORD
-
OAJ
7h 18m1 stop
Delta Logo
2:21 pm - 6:49 pm
OAJ
-
ORD
5h 28m1 stop
$496Delta
Mon, Jan 12 - Fri, Jan 16
American Airlines Logo
3:21 pm - 10:58 pm
ORD
-
OAJ
6h 37m1 stop
American Airlines Logo
3:25 pm - 7:50 pm
OAJ
-
ORD
5h 25m1 stop
$549American Airlines
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 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago to Jacksonville were found on Delta ($350) and American Airlines ($358).

Which airlines fly non-stop between Chicago O'Hare Intl Airport and Jacksonville?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Chicago O'Hare Intl Airport to Jacksonville.

There is just one airline that flies from Chicago O'Hare Intl Airport to Jacksonville direct and that is American Airlines. The best round-trip deal found from American Airlines for the route is $256.

Good to know

Cheapest flight$181
Most popular time to fly and prices are also 24% 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 $165 for a one-way ticket and $350 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.
7.2
American AirlinesOverall score based on 11073 reviews
8.0Crew
7.2Comfort
6.4Food
6.9Entertainment
7.5Boarding
Airline reviews

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

6.0 GoodDan, Dec 2025
ORD - LEX
Read more American Airlines reviews

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

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

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

Information on your arrival and departure airports