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 4/29. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$257
Delta
Wed 4/1Tue 4/14
ORD - OAJ • 1 stop
Cheapest one-way
$129
American Airlines
Wed 4/29
ORD - OAJ • 1 stop
Top airlines
Delta
Cheapest • from $257 (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 $356 (round-trip)
Charlotte (CLT)
Shortest trip • 4h 39m (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

Wed, Apr 1 - Tue, Apr 14
Delta Logo
5:30 am - 11:12 am
ORD
-
OAJ
4h 42m
1 stop
Delta Logo
2:20 pm - 6:35 pm
OAJ
-
ORD
5h 15m
1 stop
$257Delta
Tue, Mar 31 - Tue, Apr 14
Delta Logo
5:30 am - 11:12 am
ORD
-
OAJ
4h 42m
1 stop
Delta Logo
6:49 pm - 10:21 pm
OAJ
-
ORD
4h 32m
1 stop
$277Delta
Mon, Apr 27 - Thu, Apr 30
American Airlines Logo
6:05 am - 1:01 pm
ORD
-
OAJ
5h 56m
1 stop
American Airlines Logo
5:10 am - 8:30 am
OAJ
-
ORD
4h 20m
1 stop
$281American Airlines
Tue, Mar 31 - Thu, Apr 9
Delta Logo
5:30 am - 1:40 pm
ORD
-
OAJ
7h 10m
1 stop
Delta Logo
6:51 pm - 11:54 pm
OAJ
-
ORD
6h 03m
1 stop
$289Delta
Tue, Mar 24 - Thu, Mar 26
American Airlines Logo
5:00 am - 10:57 am
ORD
-
OAJ
4h 57m
1 stop
American Airlines Logo
5:00 am - 9:08 am
OAJ
-
ORD
5h 08m
1 stop
$301American Airlines
Wed, Apr 1 - Tue, Apr 14
Delta Logo
5:30 am - 11:12 am
ORD
-
OAJ
4h 42m
1 stop
Delta Logo
6:49 pm - 10:21 pm
OAJ
-
ORD
4h 32m
1 stop
$303Delta
Tue, Mar 31 - Fri, Apr 10
Delta Logo
5:30 am - 1:40 pm
ORD
-
OAJ
7h 10m
1 stop
Delta Logo
6:51 pm - 11:54 pm
OAJ
-
ORD
6h 03m
1 stop
$337Delta
Fri, May 1 - Wed, May 6
Delta Logo
5:15 am - 11:18 am
ORD
-
OAJ
5h 03m
1 stop
Delta Logo
2:20 pm - 8:16 pm
OAJ
-
ORD
6h 56m
1 stop
$340Delta
Tue, Mar 31 - Wed, Apr 8
Delta Logo
5:30 am - 11:12 am
ORD
-
OAJ
4h 42m
1 stop
Delta Logo
2:21 pm - 6:53 pm
OAJ
-
ORD
5h 32m
1 stop
$348Delta
Mon, Mar 30 - Fri, Apr 10
American Airlines Logo
5:00 pm - 11:55 pm
ORD
-
OAJ
5h 55m
1 stop
American Airlines Logo
5:10 am - 8:30 am
OAJ
-
ORD
4h 20m
1 stop
$349American 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 ($257) and American Airlines ($281).

Find 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?

    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 11397 reviews
7.5Boarding
6.9Entertainment
8.0Crew
7.2Comfort
6.4Food
Airline reviews

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

6.0 GoodIrene, Mar 2026
ORD - SDF
Read more American Airlines reviews

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

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.

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

Information on your arrival and departure airports

Chicago (ORD)
Jacksonville (OAJ)