OAJ - ORD

$333 Find Cheap Flights from Jacksonville to Chicago O'Hare Airport

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Jacksonville to Chicago departing on 8/13. 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
$333
Delta
Thu 8/13Sat 8/15
OAJ - ORD • 1 stop
Top airlines
Cheapest • from $333 (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 $534 (round-trip)
Shortest trip • 4h 57m (one-way)
Insights
Insights
Insights
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 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, Aug 13 - Sat, Aug 15
Delta Logo
6:48 pm - 11:57 pm
OAJ
-
ORD
6h 09m
1 stop
Delta Logo
8:05 am - 3:20 pm
ORD
-
OAJ
6h 15m
1 stop
$333Delta
Thu, Oct 1 - Mon, Oct 5
Delta Logo
6:00 am - 12:40 pm
OAJ
-
ORD
7h 40m
1 stop
Delta Logo
6:40 am - 1:41 pm
ORD
-
OAJ
6h 01m
1 stop
$349Delta
Thu, Oct 1 - Mon, Oct 5
Delta Logo
12:00 pm - 6:45 pm
OAJ
-
ORD
7h 45m
1 stop
Delta Logo
7:05 am - 5:54 pm
ORD
-
OAJ
9h 49m
2 stops
$354Delta
Thu, Oct 1 - Mon, Oct 5
Delta Logo
12:00 pm - 10:18 pm
OAJ
-
ORD
11h 18m
2 stops
Delta Logo
1:55 pm - 10:22 pm
ORD
-
OAJ
7h 27m
2 stops
$359Delta
Thu, Aug 13 - Sat, Aug 15
Delta Logo
6:48 pm - 11:57 pm
OAJ
-
ORD
6h 09m
1 stop
Delta Logo
11:22 am - 10:29 pm
ORD
-
OAJ
10h 07m
2 stops
$388Delta
Thu, Aug 13 - Sat, Aug 15
Delta Logo
2:27 pm - 8:30 pm
OAJ
-
ORD
7h 03m
2 stops
Delta Logo
8:05 am - 3:20 pm
ORD
-
OAJ
6h 15m
1 stop
$427Delta
Thu, Jul 23 - Mon, Jul 27
American Airlines Logo
6:37 am - 12:19 pm
OAJ
-
ORD
6h 42m
1 stop
American Airlines Logo
6:30 am - 2:32 pm
ORD
-
OAJ
7h 02m
1 stop
$442American Airlines
Thu, Jul 23 - Mon, Jul 27
American Airlines Logo
1:14 pm - 4:46 pm
OAJ
-
ORD
4h 32m
1 stop
American Airlines Logo
5:07 am - 12:48 pm
ORD
-
OAJ
6h 41m
1 stop
$475American Airlines
Fri, Jul 3 - Mon, Jul 6
Delta Logo
6:40 pm - 11:59 pm
OAJ
-
ORD
6h 19m
1 stop
Delta Logo
5:30 am - 11:21 am
ORD
-
OAJ
4h 51m
1 stop
$513Delta
Thu, Aug 13 - Sat, Aug 15
Delta Logo
12:10 pm - 6:29 pm
OAJ
-
ORD
7h 19m
2 stops
Delta Logo
11:22 am - 10:29 pm
ORD
-
OAJ
10h 07m
2 stops
$537Delta
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 5 days.

In the past 5 days, the cheapest round-trip tickets from Jacksonville to Chicago O'Hare Airport were found on Delta ($333) and American Airlines ($423).

Good to know

Cheapest flight$333
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 5 days, the lowest price for a flight from Jacksonville to Chicago O'Hare Intl Airport was $333 for a round-trip ticket.

  • 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 11746 reviews
7.9Crew
7.5Boarding
6.8Entertainment
6.4Food
7.2Comfort
Airline reviews

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

6.0 GoodHardin, Jun 2026
ICT - ORD
Read more American Airlines reviews

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

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

Information on your arrival and departure airports