OAJ - ORD

$148 Find Cheap Flights from Jacksonville to Chicago O'Hare Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Jacksonville to Chicago departing on 5/4. 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 Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Jacksonville to Chicago, 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 Jacksonville to Chicago, 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
$288
Delta
Thu 5/28Wed 6/3
OAJ - ORD • 1 stop
Cheapest one-way
$148
Delta
Mon 5/4
OAJ - ORD • 1 stop
Top airlines
Cheapest • from $288 (round-trip)
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 Jacksonville and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $467 (round-trip)
Shortest trip • 5h 00m (one-way)
Insights
Insights
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Jacksonville to Chicago (OAJ-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Jacksonville to Chicago 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 Jacksonville to Chicago

Thu, May 28 - Wed, Jun 3
Delta Logo
6:47 pm - 11:59 pm
OAJ
-
ORD
6h 12m
1 stop
Delta Logo
8:10 am - 3:27 pm
ORD
-
OAJ
6h 17m
1 stop
$288Delta
Tue, Apr 7 - Tue, Apr 14
Delta Logo
6:51 pm - 11:54 pm
OAJ
-
ORD
6h 03m
1 stop
Delta Logo
7:10 am - 1:40 pm
ORD
-
OAJ
5h 30m
1 stop
$378Delta
Tue, Apr 7 - Thu, Apr 16
Delta Logo
6:51 pm - 11:54 pm
OAJ
-
ORD
6h 03m
1 stop
Delta Logo
5:15 am - 11:18 am
ORD
-
OAJ
5h 03m
1 stop
$385Delta
Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
8:03 pm - 11:48 pm
OAJ
-
ORD
4h 45m
1 stop
American Airlines Logo
5:20 am - 12:56 pm
ORD
-
OAJ
6h 36m
1 stop
$397American Airlines
Thu, Apr 9 - Wed, Apr 15
Delta Logo
6:51 pm - 11:54 pm
OAJ
-
ORD
6h 03m
1 stop
Delta Logo
5:15 am - 1:40 pm
ORD
-
OAJ
7h 25m
1 stop
$404Delta
Thu, Apr 9 - Thu, Apr 16
Delta Logo
6:51 pm - 11:54 pm
OAJ
-
ORD
6h 03m
1 stop
Delta Logo
5:15 am - 11:18 am
ORD
-
OAJ
5h 03m
1 stop
$411Delta
Fri, Aug 7 - Mon, Aug 10
American Airlines Logo
8:03 pm - 11:48 pm
OAJ
-
ORD
4h 45m
1 stop
American Airlines Logo
6:25 pm - 11:55 pm
ORD
-
OAJ
4h 30m
1 stop
$422American Airlines
Thu, Jul 23 - Fri, Jul 24
Delta Logo
6:44 pm - 11:53 pm
OAJ
-
ORD
6h 09m
1 stop
Delta Logo
1:44 pm - 10:30 pm
ORD
-
OAJ
7h 46m
1 stop
$428Delta
Tue, Apr 7 - Tue, Apr 14
Delta Logo
6:51 pm - 11:54 pm
OAJ
-
ORD
6h 03m
1 stop
Delta Logo
9:35 am - 10:51 pm
ORD
-
OAJ
12h 16m
2 stops
$436Delta
Wed, May 20 - Tue, May 26
American Airlines Logo
5:10 am - 8:30 am
OAJ
-
ORD
4h 20m
1 stop
American Airlines Logo
6:55 am - 12:49 pm
ORD
-
OAJ
4h 54m
1 stop
$453American Airlines
Booking Insights

KAYAK's insights & trends for Jacksonville to Chicago flights

Get data-powered insights and trends into flights from Jacksonville to Chicago to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Jacksonville to Chicago O'Hare Airport?

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 Jacksonville to Chicago O'Hare Airport were found on Delta ($288) and American Airlines ($397).

Good to know

Cheapest flight$148
Flight from Jacksonville to Chicago O'Hare Airport

When to book flights from Jacksonville to Chicago

Are your dates flexible? Find out the best times to travel from Jacksonville to Chicago 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 Jacksonville to Chicago O'Hare Airport flights

  • What is the cheapest flight from Jacksonville to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Jacksonville to Chicago O'Hare Intl Airport was $148 for a one-way ticket and $288 for a round-trip.

  • Do I need a passport to fly between Jacksonville and Chicago O'Hare Airport?

    No

  • Which aircraft models fly most regularly from Jacksonville to Chicago O'Hare Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Jacksonville to Chicago O'Hare Airport?

    oneworld is the only airline alliance operating flights between Jacksonville and Chicago O'Hare Airport.

  • How does KAYAK find such low prices on flights from Jacksonville to Chicago O'Hare Airport?

    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 Jacksonville to Chicago O'Hare Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Jacksonville to Chicago O'Hare Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport from Jacksonville 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 Jacksonville to Chicago O'Hare Airport?

    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 Chicago O'Hare Airport with an airline and back to Jacksonville with another airline. Booking your flights between Jacksonville and ORD 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 Jacksonville to Chicago O'Hare Airport?

    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 Chicago O'Hare Airport from Jacksonville 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 Jacksonville to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Jacksonville to Chicago. 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 Jacksonville to Chicago? 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 11496 reviews
7.9Crew
7.5Boarding
6.9Entertainment
7.2Comfort
6.4Food
Airline reviews

Delays with no explanation. It could have been handled better.

4.0 OkayMushtaque, Mar 2026
DCA - ORD
Read more American Airlines reviews

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

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

Information on your arrival and departure airports