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$257+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAJ
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap 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 September 15, 2025.

Round-trip from

$257
(Delta)

Popular in

December

Cheapest in

October

Average price

$390
From Chicago (CHI) to Jacksonville Albert J Ellis
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($88 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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Find 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 September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/12. 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.
Thu 10/27:02 amORD - OAJ
1 stop6h 14mAmerican Airlines
Sun 10/56:10 pmOAJ - ORD
1 stop6h 29mAmerican Airlines
Deal found 9/12$308
This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 11/271:09 pmORD - OAJ
1 stop6h 49mDelta
Tue 12/211:50 amOAJ - ORD
1 stop5h 53mDelta
Deal found 9/15$339
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Thu 10/308:35 amORD - OAJ
1 stop4h 25mAmerican Airlines
Sat 11/81:18 pmOAJ - ORD
1 stop7h 24mAmerican Airlines
Deal found 9/13$363
This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 11/276:00 amMDW - OAJ
1 stop5h 44mDelta
Tue 12/211:50 amOAJ - MDW
1 stop5h 46mDelta
Deal found 9/15$399
This Delta deal was found by Cheapflights users on 9/15. 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.
Sat 10/411:00 amMDW - OAJ
1 stop4h 20mDelta
Mon 10/611:53 amOAJ - MDW
1 stop5h 16mDelta
Deal found 9/15$401
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 11/273:10 pmORD - OAJ
2 stops18h 23mAmerican Airlines
Tue 12/27:02 pmOAJ - ORD
1 stop5h 35mAmerican Airlines
Deal found 9/15$401
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Thu 9/258:38 amORD - OAJ
1 stop4h 38mAmerican Airlines
Sun 9/288:02 pmOAJ - ORD
1 stop4h 37mAmerican Airlines
Deal found 9/13$476
This Delta deal was found by Cheapflights users on 9/12. 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.
Thu 10/26:00 amMDW - OAJ
1 stop4h 08mDelta
Sun 10/55:52 amOAJ - MDW
1 stop6h 56mDelta
Deal found 9/12$477
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Fri 9/197:02 amORD - OAJ
1 stop5h 54mAmerican Airlines
Sun 9/216:10 pmOAJ - ORD
1 stop6h 29mAmerican Airlines
Deal found 9/13$485
This Delta deal was found by Cheapflights users on 9/14. 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.
Tue 12/233:57 pmORD - OAJ
1 stop4h 39mDelta
Tue 12/305:40 amOAJ - ORD
1 stop6h 46mDelta
Deal found 9/14$494
This Delta deal was found by Cheapflights users on 9/14. 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.
Mon 9/296:00 amMDW - OAJ
1 stop4h 08mDelta
Fri 10/35:52 amOAJ - MDW
1 stop4h 48mDelta
Deal found 9/14$525
This Delta deal was found by Cheapflights users on 9/14. 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.
Tue 12/239:54 amMDW - OAJ
1 stop7h 09mDelta
Tue 12/305:40 amOAJ - MDW
1 stop4h 29mDelta
Deal found 9/14$574

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 September 15, 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

MDW - OAJ

MDWOAJ

Chicago Midway

Fri 1/23

6:00 am-1:39 pm

1 stop6h 39m

Jacksonville Albert J Ellis

Wed 1/28

4:00 pm-9:46 pm

1 stop6h 46m

$257

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Wed 1/21

6:00 am-11:10 am

1 stop4h 10m

Jacksonville Albert J Ellis

Mon 1/26

6:25 pm-9:46 pm

1 stop4h 21m

$298

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Thu 10/2

7:02 am-2:16 pm

1 stop6h 14m

Jacksonville Albert J Ellis

Sun 10/5

6:10 pm-11:39 pm

1 stop6h 29m

$308

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Sun 11/2

5:00 am-10:33 am

1 stop4h 33m

Jacksonville Albert J Ellis

Tue 11/4

7:02 pm-11:37 pm

1 stop5h 35m

$308

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Wed 1/21

6:00 am-11:10 am

1 stop4h 10m

Jacksonville Albert J Ellis

Tue 1/27

5:40 am-12:01 pm

1 stop7h 21m

$339

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Thu 11/27

1:09 pm-8:58 pm

1 stop6h 49m

Jacksonville Albert J Ellis

Tue 12/2

11:50 am-4:43 pm

1 stop5h 53m

$339

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Thu 10/30

8:35 am-2:00 pm

1 stop4h 25m

Jacksonville Albert J Ellis

Sat 11/8

1:18 pm-7:42 pm

1 stop7h 24m

$363

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Thu 1/22

6:00 am-11:10 am

1 stop4h 10m

Jacksonville Albert J Ellis

Tue 1/27

5:40 am-9:56 am

1 stop5h 16m

$363

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Fri 1/23

6:00 am-1:39 pm

1 stop6h 39m

Jacksonville Albert J Ellis

Tue 1/27

5:40 am-12:01 pm

1 stop7h 21m

$371

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Wed 1/21

9:20 am-10:14 pm

2 stops11h 54m

Jacksonville Albert J Ellis

Wed 1/28

12:00 pm-4:25 pm

1 stop5h 25m

$372

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 17 results
1
2

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, August is the cheapest month in which you can book a flight from Chicago to Jacksonville, North Carolina (average of $366). Flying from Chicago to Jacksonville, North Carolina in December is currently the most expensive (average of $490). 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 September 15, 2025.
See what other customers who have flown with Delta and 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.
Delta
8.0
Very good
7,954 reviews

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,954 reviews

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 6h 14m. 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 $276. This flight start at 37% 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, August is the cheapest month in which you can book a flight from Chicago to Jacksonville, North Carolina (average of $366). Flying from Chicago to Jacksonville, North Carolina in December is currently the most expensive (average of $490). 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.

See more FAQs

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$276Average$434FlexibilityNo cancel feeOn-time71%

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