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$305+ Cheap flights from Chicago (CHI) to Jacksonville, NC (OAJ)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAJ
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Chicago to Jacksonville

Cheapest flights from Chicago to Jacksonville
Explore the most affordable flight options available from Chicago to Jacksonville. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:00 amORD - OAJ
1 stop4h 23mAmerican Airlines
Sun 1/47:55 pmOAJ - ORD
1 stop4h 47mAmerican Airlines
Deal found 12/16$514
This Delta deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:29 pmMDW - OAJ
1 stop5h 07mDelta
Sun 1/46:42 pmOAJ - MDW
1 stop4h 40mDelta
Deal found 12/16$719

Find flight deals from Chicago to Jacksonville

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Jacksonville (OAJ). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$305
(Delta)

Popular in

December

Cheapest in

January

Average price

$708
Provider with most accurate pricing for Chicago (CHI)-Jacksonville Albert J Ellis flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Jacksonville Albert J Ellis flights.
Search Deals
From Chicago (CHI) to Jacksonville Albert J Ellis
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Jacksonville that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Chicago to Jacksonville that are best for you.

Fly from

Chicago

Fly to

Jacksonville

Route

Depart

Return

Price

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Sun 1/18

5:30 am-11:04 am

1 stop4h 34m

Jacksonville Albert J Ellis

Tue 1/27

5:40 am-10:05 am

1 stop5h 25m

$305

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Wed 2/11

7:10 am-9:42 pm

2 stops13h 32m

Jacksonville Albert J Ellis

Sat 2/14

11:42 am-4:54 pm

1 stop6h 12m

$310

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Thu 2/12

5:25 am-11:02 am

1 stop4h 37m

Jacksonville Albert J Ellis

Sat 2/14

5:40 am-10:07 am

1 stop5h 27m

$337

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Tue 2/17

6:20 am-1:38 pm

1 stop6h 18m

Jacksonville Albert J Ellis

Tue 2/24

11:24 am-4:39 pm

1 stop6h 15m

$339

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Wed 2/11

7:05 am-2:54 pm

1 stop6h 49m

Jacksonville Albert J Ellis

Fri 2/13

5:40 am-10:08 am

1 stop5h 28m

$345

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Thu 2/12

5:00 am-12:38 pm

1 stop6h 38m

Jacksonville Albert J Ellis

Sat 2/14

10:58 am-5:31 pm

2 stops7h 33m

$363

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Thu 2/12

6:45 am-1:33 pm

1 stop5h 48m

Jacksonville Albert J Ellis

Fri 2/13

5:40 am-10:08 am

1 stop5h 28m

$377

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Sun 1/18

6:45 am-3:50 pm

1 stop8h 05m

Jacksonville Albert J Ellis

Tue 1/27

5:40 am-11:59 am

1 stop7h 19m

$400

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Wed 2/11

5:30 am-11:04 am

1 stop4h 34m

Jacksonville Albert J Ellis

Sun 2/15

11:42 am-4:49 pm

1 stop6h 07m

$400

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Thu 1/1

5:00 am-10:23 am

1 stop4h 23m

Jacksonville Albert J Ellis

Mon 1/5

7:55 pm-11:42 pm

1 stop4h 47m

$413

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 12 results
1
2

Compare providers for flights from Chicago to Jacksonville

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Jacksonville in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Jacksonville, North Carolina flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Jacksonville, North Carolina flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Jacksonville, North Carolina flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Jacksonville, North Carolina flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Jacksonville, North Carolina flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Jacksonville

Have a flexible travel schedule? Discover the best time to fly to Jacksonville from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Chicago to Jacksonville, North Carolina?

Currently, November is the cheapest month in which you can book a flight from Chicago to Jacksonville, North Carolina (average of $160). Flying from Chicago to Jacksonville, North Carolina in December is currently the most expensive (average of $268). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Jacksonville

Get insights into the airlines that provide service to Jacksonville. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jacksonville. Reviews last updated December 18, 2025.
See what other customers who have flown with American Airlines from Chicago to Jacksonville have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,055 reviews

Entertainment

6.9

Food

6.5

Crew

8.0

Boarding

7.5

Overall

7.2

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,055 reviews
American Airlines
7.2
Good
11,055 reviews

Entertainment

6.9

Food

6.5

Crew

8.0

Boarding

7.5

Overall

7.2

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

Related info for your journey

Find useful and relevant information for your journey from Chicago to Jacksonville. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Jacksonville from Chicago?

    If you book a flight to Jacksonville from Chicago, you will be flying to Albert J Ellis, which is the city’s only airport. Jacksonville Albert J Ellis (OAJ) is located 11.3 mi from the center of Jacksonville. There are 0 flights from Chicago to Albert J Ellis per day from 1 airline.

  • How long is the flight from Chicago to Jacksonville, North Carolina?

    Departing from Chicago to Jacksonville, North Carolina will take you 4h 34m. The distance from Chicago to Jacksonville, North Carolina is about 743 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly from Chicago to Jacksonville, North Carolina round-trip?

    Flying on American Airlines is currently your cheapest option to Jacksonville, North Carolina, with prices starting at $256. This flight start at 40% lower than the current average price 3 months from now.

  • Can I find deals for flights from Chicago to Jacksonville that include hotel bookings?

    Yes. In addition to deals on Chicago to Jacksonville flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Jacksonville?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Jacksonville.

  • Can I find deals for business class flights from Chicago to Jacksonville?

    Yes. Cheapflights offers flight deals from Chicago to Jacksonville by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, November is the cheapest month in which you can book a flight from Chicago to Jacksonville, North Carolina (average of $160). Flying from Chicago to Jacksonville, North Carolina in December is currently the most expensive (average of $268). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Top airline flying from Chicago to Jacksonville

Discover the top airline that operate flights from Chicago to Jacksonville. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$256Average$456FlexibilityNo cancel feeOn-time71%

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