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OAJ - CHI

$200 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 8/8. 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
Mon 6/3
Mon 6/10

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 43,369,418 times on KAYAK, and here is why:

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

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 and deals for you by selecting your travel dates.
Choose your dates
5:50 am - 12:04 pmOAJ-ORD
7h 14m1 stop
3:35 pm - 10:54 pmORD-OAJ
6h 19m1 stop
$367Delta
Find Deal
Wed, Oct 30 - Sat, Nov 2
5:50 am - 5:49 pmOAJ-ORD
12h 59m2 stops
3:35 pm - 10:54 pmORD-OAJ
6h 19m1 stop
$372Delta
Find Deal
Wed, Oct 30 - Sat, Nov 2
5:50 am - 9:17 amOAJ-MDW
4h 27m1 stop
11:59 am - 10:54 pmMDW-OAJ
9h 55m2 stops
$372Delta
Find Deal
Wed, Oct 30 - Sat, Nov 2
5:50 am - 4:12 pmOAJ-ORD
11h 22m2 stops
1:35 pm - 10:54 pmORD-OAJ
8h 19m2 stops
$377Delta
Find Deal
Wed, Oct 30 - Sat, Nov 2
5:50 am - 9:17 amOAJ-MDW
4h 27m1 stop
10:11 am - 10:54 pmMDW-OAJ
11h 43m1 stop
$389Delta
Find Deal
Wed, Oct 30 - Sat, Nov 2
5:50 am - 9:17 amOAJ-MDW
4h 27m1 stop
5:50 pm - 1:26 pmMDW-OAJ
18h 36m2 stops
$444Delta
Find Deal
Wed, Oct 30 - Sat, Nov 2
5:50 am - 8:45 amOAJ-MDW
27h 55m2 stops
11:59 am - 10:54 pmMDW-OAJ
9h 55m2 stops
$518Delta
Find Deal
Wed, Oct 30 - Sat, Nov 2
5:44 am - 11:12 amOAJ-ORD
6h 28m1 stop
6:00 am - 12:29 pmORD-OAJ
5h 29m1 stop
$528Delta
Find Deal
Fri, Jun 28 - Sun, Jun 30
8:32 pm - 11:59 pmOAJ-ORD
4h 27m1 stop
6:25 pm - 11:59 pmORD-OAJ
4h 34m1 stop
$565American Airlines
Find Deal
Sun, Jun 2 - Sun, Jun 9
8:32 pm - 9:15 amOAJ-ORD
13h 43m2 stops
5:30 am - 10:29 amORD-OAJ
3h 59m1 stop
$739American Airlines
Find Deal
Sun, Jun 2 - Sun, Jun 9

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 Friday 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 American Airlines for $200. Delta proposed a round-trip connection from $367 and American Airlines from $565.

Good to know

Cheapest flight

$200
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 $200 for a one-way ticket and $367 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?

    oneworld, and SkyTeam 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 14728 reviews
8.0Crew
7.6Boarding
6.6Food
7.1Entertainment
7.2Comfort
Airline reviews

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.

6.0 GoodAnonymous, Apr 2024SPI - ORD
Read more about American Airlines reviews

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.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

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.
8/8Thu
1 stopAmerican Airlines
6h 38mOAJ-ORD
$200
8/8Thu
2 stopsDelta
11h 15mOAJ-ORD
$244
8/8Thu
1 stopDelta
5h 44mOAJ-MDW
$289
8/8Thu
2 stopsDelta
7h 47mOAJ-ORD
$394
8/8Thu
2 stopsDelta
7h 41mOAJ-MDW
$394
8/8Thu
2 stopsDelta
7h 41mOAJ-MDW
$463

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Jacksonville - Chicago Flights

Departure:

Jacksonville (OAJ)United States

Return flight deals:

Chicago - Jacksonville

Cabin classes: