ORD - OAJ

$274 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 3/5. 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
$311
Delta
Wed 3/11Wed 3/18
ORD - OAJ • 1 stop
Cheapest one-way
$274
American Airlines
Thu 3/5
ORD - OAJ • 1 stop
Top airlines
Delta
Cheapest • from $311 (round-trip)
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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

Wed, Mar 11 - Wed, Mar 18
Delta Logo
5:30 am - 11:12 am
ORD
-
OAJ
4h 42m
1 stop
Delta Logo
11:58 am - 4:49 pm
OAJ
-
ORD
5h 51m
1 stop
$311Delta
Sat, May 9 - Tue, May 12
Delta Logo
9:10 am - 3:27 pm
ORD
-
OAJ
5h 17m
1 stop
Delta Logo
4:07 pm - 10:28 pm
OAJ
-
ORD
7h 21m
1 stop
$339Delta
Fri, Apr 24 - Sun, Apr 26
Delta Logo
5:10 am - 11:18 am
ORD
-
OAJ
5h 08m
1 stop
Delta Logo
5:40 am - 10:09 am
OAJ
-
ORD
5h 29m
1 stop
$357Delta
Wed, Feb 18 - Wed, Feb 25
Delta Logo
2:46 pm - 10:35 pm
ORD
-
OAJ
6h 49m
1 stop
Delta Logo
11:48 am - 4:51 pm
OAJ
-
ORD
6h 03m
1 stop
$373Delta
Wed, Feb 18 - Wed, Feb 25
American Airlines Logo
6:08 am - 1:38 pm
ORD
-
OAJ
6h 30m
2 stops
American Airlines Logo
7:16 pm - 12:06 am
OAJ
-
ORD
5h 50m
1 stop
$378American Airlines
Thu, Apr 23 - Sun, Apr 26
Delta Logo
7:14 am - 1:40 pm
ORD
-
OAJ
5h 26m
1 stop
Delta Logo
5:40 am - 10:09 am
OAJ
-
ORD
5h 29m
1 stop
$398Delta
Fri, May 8 - Mon, May 11
Delta Logo
6:00 am - 1:40 pm
ORD
-
OAJ
6h 40m
1 stop
Delta Logo
6:25 pm - 11:55 pm
OAJ
-
ORD
6h 30m
1 stop
$418Delta
Wed, Feb 18 - Wed, Feb 25
Delta Logo
2:46 pm - 10:35 pm
ORD
-
OAJ
6h 49m
1 stop
Delta Logo
11:48 am - 4:51 pm
OAJ
-
ORD
6h 03m
1 stop
$421Delta
Wed, Feb 18 - Wed, Feb 25
American Airlines Logo
6:08 am - 1:38 pm
ORD
-
OAJ
6h 30m
2 stops
American Airlines Logo
7:16 pm - 12:06 am
OAJ
-
ORD
5h 50m
1 stop
$426American Airlines
Wed, Feb 18 - Wed, Feb 25
American Airlines Logo
6:08 am - 1:38 pm
ORD
-
OAJ
6h 30m
2 stops
American Airlines Logo
7:18 am - 1:19 pm
OAJ
-
ORD
7h 01m
2 stops
$472American 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 ($311) and American Airlines ($378).

Good to know

Cheapest flight$274
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 $274 for a one-way ticket and $311 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 11211 reviews
6.9Entertainment
7.2Comfort
7.5Boarding
6.4Food
8.0Crew
Airline reviews

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

2.0 MediocreAnuj, Jan 2026
ORD - DFW
Read more American Airlines reviews

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

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.

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

Information on your arrival and departure airports