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OAJ - CHI

$399 Find cheap flights from Jacksonville, North Carolina to Chicago

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 6/28. 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
0 bags
Thu 6/27
Thu 7/4

Search hundreds of travel sites at once for deals on flights to Chicago

 
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
In the last 7 days travelers have searched 42,816,550 times on KAYAK, and here is why:

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Cheap flight deals from Jacksonville to Chicago (OAJ-CHI)

 
These are the cheapest deals for flights from Jacksonville to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Jacksonville to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Jacksonville to Chicago.

Recent one-way flight deals from Jacksonville to Chicago

Only flying one-way? Below are some of the best one-way flight deals from Jacksonville to Chicago found on KAYAK recently.

Recent last minute flight deals from Jacksonville to Chicago

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Jacksonville to Chicago.

Recent direct flight deals from Jacksonville to Chicago

The latest deals for direct flights from Jacksonville to Chicago so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Jacksonville to Chicago

Find recent round-trip train or bus tickets from Jacksonville to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:01 pm - 11:58 pmOAJ-ORD
6h 57m1 stop
4:46 pm - 11:59 pmORD-OAJ
6h 13m1 stop
$551American Airlines
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Wed, Jun 26 - Wed, Jul 3
6:01 pm - 11:58 pmOAJ-ORD
6h 57m1 stop
8:28 pm - 10:29 amORD-OAJ
13h 01m2 stops
$617American Airlines
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Wed, Jun 26 - Wed, Jul 3
5:44 am - 3:37 pmOAJ-ORD
10h 53m2 stops
10:06 am - 10:54 pmORD-OAJ
11h 48m2 stops
$648Delta
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Wed, Jun 26 - Wed, Jul 3
1:09 pm - 5:59 pmOAJ-MDW
5h 50m1 stop
3:45 pm - 10:54 pmMDW-OAJ
6h 09m1 stop
$718Delta
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Wed, Jun 26 - Wed, Jul 3
5:44 am - 11:55 amOAJ-MDW
7h 11m1 stop
1:24 pm - 10:54 pmMDW-OAJ
8h 30m2 stops
$723Delta
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Wed, Jun 26 - Wed, Jul 3
5:44 am - 12:43 pmOAJ-MDW
7h 59m2 stops
1:24 pm - 10:54 pmMDW-OAJ
8h 30m2 stops
$758Delta
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Wed, Jun 26 - Wed, Jul 3
5:44 am - 11:12 amOAJ-ORD
6h 28m1 stop
$399Delta
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Fri, Jun 28
5:44 am - 9:51 amOAJ-MDW
5h 07m1 stop
$399Delta
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Fri, Jun 28
7:03 am - 6:41 pmOAJ-ORD
12h 38m2 stops
$402American Airlines
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Fri, Jun 28
5:44 am - 12:43 pmOAJ-MDW
7h 59m2 stops
$1,015Delta
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Fri, Jun 28
1:07 pm - 4:47 pmOAJ-ORD
4h 40m1 stop
3:32 pm - 11:32 pmORD-OAJ
7h 00m1 stop
$710Delta
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Thu, May 30 - Sat, Jun 1
1:07 pm - 5:58 pmOAJ-MDW
5h 51m1 stop
6:00 am - 12:27 pmMDW-OAJ
5h 27m1 stop
$710Delta
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Thu, May 30 - Sat, Jun 1
1:07 pm - 10:44 pmOAJ-ORD
10h 37m2 stops
3:32 pm - 11:32 pmORD-OAJ
7h 00m1 stop
$715Delta
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Thu, May 30 - Sat, Jun 1
5:55 am - 1:35 pmOAJ-MDW
8h 40m2 stops
6:00 am - 12:27 pmMDW-OAJ
5h 27m1 stop
$715Delta
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Thu, May 30 - Sat, Jun 1
1:07 pm - 10:39 pmOAJ-ORD
10h 32m2 stops
12:20 pm - 11:32 pmORD-OAJ
10h 12m2 stops
$720Delta
Find Deal
Thu, May 30 - Sat, Jun 1
5:55 am - 1:35 pmOAJ-MDW
8h 40m2 stops
11:59 am - 11:32 pmMDW-OAJ
10h 33m2 stops
$720Delta
Find Deal
Thu, May 30 - Sat, Jun 1

Flights from Jacksonville to Chicago - Travel Insights & Trends

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.

What’s the cheapest day of the week to fly from Jacksonville to Chicago?

The average price of all flights from Jacksonville, North Carolina to Chicago clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Jacksonville to Chicago, look for departures on Mondays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Chicago, Wednesday is the cheapest day to fly and Saturday is the most expensive.

Which airlines provide the cheapest flights from Jacksonville to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Jacksonville to Chicago found on KAYAK was with Delta for $399. American Airlines proposed a round-trip connection from $551 and Delta from $648.

Good to know

Cheapest flight

$399
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 flights from Jacksonville to Chicago

  • What is the cheapest flight from Jacksonville, North Carolina to Chicago?

    In the last 3 days, the lowest price for a flight from Jacksonville, North Carolina to Chicago was $399 for a one-way ticket and $551 for a round-trip.

  • Do I need a passport to fly between Jacksonville and Chicago?

    A passport is not required to fly from Jacksonville to Chicago.

  • Which airports will I be using when flying from Jacksonville to Chicago?

    On your way to Chicago, you’ll fly out from Jacksonville Albert J Ellis. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Jacksonville to Chicago?

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

  • Which airline alliances offer flights from Jacksonville to Chicago?

    SkyTeam, and oneworld are the airline alliances operating flights between Jacksonville and Chicago, with SkyTeam being the most commonly used for this route.

  • How does KAYAK find such low prices on flights from Jacksonville to Chicago?

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago 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?

    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 with an airline and back to Jacksonville with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Jacksonville to Chicago?

    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 from Jacksonville up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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.
7.3
American AirlinesOverall score based on 14316 reviews
7.2Comfort
7.6Boarding
7.1Entertainment
8.0Crew
6.6Food
Airline reviews

The CX617 from HK to BKK was delayed more than 1.5 hours.

2.0 MediocreAnonymous, May 2024STL - ORD
Read more about American Airlines reviews

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Book cheap flights from Jacksonville to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Jacksonville to Chicago found on KAYAK in the last 72 hours.
6/28Fri
1 stopDelta
6h 28mOAJ-ORD
$399
6/28Fri
1 stopDelta
5h 07mOAJ-MDW
$399
6/28Fri
2 stopsAmerican Airlines
12h 38mOAJ-ORD
$402
6/28Fri
2 stopsDelta
7h 59mOAJ-MDW
$1,015

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Last minute flights from Jacksonville to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Jacksonville to Chicago that are departing in the next 10 days.
5/30Thu
multi-stopDelta
4h 40mOAJ-ORD
6/1Sat
multi-stopDelta
7h 00mORD-OAJ
$710
5/30Thu
multi-stopDelta
5h 51mOAJ-MDW
6/1Sat
multi-stopDelta
5h 27mMDW-OAJ
$710
5/30Thu
multi-stopDelta
10h 37mOAJ-ORD
6/1Sat
multi-stopDelta
7h 00mORD-OAJ
$715
5/30Thu
multi-stopDelta
8h 40mOAJ-MDW
6/1Sat
multi-stopDelta
5h 27mMDW-OAJ
$715
5/30Thu
multi-stopDelta
10h 32mOAJ-ORD
6/1Sat
multi-stopDelta
10h 12mORD-OAJ
$720
5/30Thu
multi-stopDelta
8h 40mOAJ-MDW
6/1Sat
multi-stopDelta
10h 33mMDW-OAJ
$720

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Jacksonville - Chicago Flights

Departure:

Jacksonville (OAJ)United States

Return flight deals:

Chicago - Jacksonville

Cabin classes: