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$195+ Cheap flights from Chicago (CHI) to Jacksonville, NC (OAJ)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAJ
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$314
(American Airlines)

One-way from

$195
(Delta)

Popular in

December

Cheapest in

August

Average price

$462
From Chicago (CHI) to Jacksonville Albert J Ellis
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One-way flight from Chicago (CHI) to Jacksonville Albert J Ellis
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Highest demand for flights based on searches. 13% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/31. 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 8/294:56 pmORD - OAJ
1 stop5h 52mAmerican Airlines
Mon 9/18:03 pmOAJ - ORD
1 stop4h 39mAmerican Airlines
Deal found 7/31$314
This Delta deal was found by Cheapflights users on 7/30. 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.
Fri 9/56:00 amMDW - OAJ
1 stop4h 10mDelta
Wed 9/105:55 amOAJ - MDW
1 stop4h 39mDelta
Deal found 7/30$342
This Delta deal was found by Cheapflights users on 7/30. 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.
Fri 9/59:47 amORD - OAJ
1 stop5h 00mDelta
Wed 9/105:55 amOAJ - ORD
1 stop7h 21mDelta
Deal found 7/30$342

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 July 31, 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

Fri 8/29

4:56 pm-11:48 pm

1 stop5h 52m

Jacksonville Albert J Ellis

Mon 9/1

8:03 pm-11:42 pm

1 stop4h 39m

$314

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Fri 9/5

6:00 am-11:10 am

1 stop4h 10m

Jacksonville Albert J Ellis

Wed 9/10

5:55 am-9:34 am

1 stop4h 39m

$342

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Fri 9/5

9:47 am-3:47 pm

1 stop5h 00m

Jacksonville Albert J Ellis

Wed 9/10

5:55 am-12:16 pm

1 stop7h 21m

$342

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Fri 9/26

10:35 am-6:15 pm

1 stop6h 40m

$195

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Fri 9/26

7:20 am-2:19 pm

1 stop5h 59m

$195

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Fri 9/26

1:37 pm-9:06 pm

2 stops6h 29m

$200

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 July 31, 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
7,981 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Comfort

7.9

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
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Comfort

7.9

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
7,981 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.5

Comfort

7.9

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.

  • What are the cheapest airlines flying 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 $314. Another option worth looking into is Delta, starting at $342 round trip. These flights start at 31% 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$276Average$416FlexibilityNo cancel feeOn-time71%

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