HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Jacksonville

$242+ 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 11/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAJ
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Jacksonville with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$297
(Delta)

One-way from

$242
(Delta)

Popular in

December

Cheapest in

January

Average price

$358
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
One-way flight from Chicago (CHI) to Jacksonville Albert J Ellis
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($80 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 30, 2025.

This Delta deal was found by Cheapflights users on 10/27. 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 11/276:45 amORD - OAJ
1 stop4h 59mDelta
Wed 12/35:30 amOAJ - ORD
1 stop7h 33mDelta
Deal found 10/27$297
This Delta deal was found by Cheapflights users on 10/27. 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 11/276:45 amORD - OAJ
1 stop4h 59mDelta
Tue 12/22:26 pmOAJ - ORD
1 stop5h 17mDelta
Deal found 10/27$308
This Delta deal was found by Cheapflights users on 10/28. 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 12/45:30 amORD - OAJ
1 stop4h 43mDelta
Thu 12/1111:53 amOAJ - ORD
1 stop4h 27mDelta
Deal found 10/28$317
This Delta deal was found by Cheapflights users on 10/27. 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 11/271:14 pmORD - OAJ
1 stop6h 24mDelta
Fri 12/511:53 amOAJ - ORD
1 stop5h 52mDelta
Deal found 10/27$327
This Delta deal was found by Cheapflights users on 10/27. 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 11/264:26 pmORD - OAJ
1 stop4h 32mDelta
Tue 12/22:26 pmOAJ - ORD
1 stop5h 17mDelta
Deal found 10/27$339
This Delta deal was found by Cheapflights users on 10/27. 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 11/265:23 amORD - OAJ
1 stop4h 53mDelta
Thu 12/411:53 amOAJ - ORD
1 stop5h 52mDelta
Deal found 10/27$347
This Delta deal was found by Cheapflights users on 10/27. 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 11/2411:19 amORD - OAJ
1 stop5h 40mDelta
Wed 12/35:30 amOAJ - ORD
1 stop5h 44mDelta
Deal found 10/27$348
This Delta deal was found by Cheapflights users on 10/27. 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 11/264:26 pmORD - OAJ
1 stop4h 32mDelta
Fri 12/511:53 amOAJ - ORD
1 stop7h 50mDelta
Deal found 10/27$358
This Delta deal was found by Cheapflights users on 10/27. 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 11/2411:19 amORD - OAJ
1 stop5h 40mDelta
Tue 12/22:26 pmOAJ - ORD
1 stop5h 17mDelta
Deal found 10/27$359
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/265:00 amORD - OAJ
1 stop6h 53mAmerican Airlines
Wed 12/36:10 amOAJ - ORD
1 stop7h 22mAmerican Airlines
Deal found 10/28$362
This Delta deal was found by Cheapflights users on 10/27. 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 10/314:23 pmMDW - OAJ
1 stop5h 20mDelta
Sun 11/25:48 amOAJ - MDW
1 stop4h 57mDelta
Deal found 10/27$432
This Delta deal was found by Cheapflights users on 10/29. 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 11/1310:47 amMDW - OAJ
1 stop6h 12mDelta
Mon 11/176:44 pmOAJ - MDW
1 stop5h 56mDelta
Deal found 10/29$487

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 October 30, 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

Thu 11/27

6:45 am-12:44 pm

1 stop4h 59m

Jacksonville Albert J Ellis

Wed 12/3

5:30 am-12:03 pm

1 stop7h 33m

$297

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Thu 11/27

1:14 pm-8:38 pm

1 stop6h 24m

Jacksonville Albert J Ellis

Fri 12/5

11:53 am-4:45 pm

1 stop5h 52m

$327

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Wed 11/26

4:26 pm-9:58 pm

1 stop4h 32m

Jacksonville Albert J Ellis

Wed 12/3

5:30 am-10:14 am

1 stop5h 44m

$339

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Wed 11/26

4:26 pm-9:58 pm

1 stop4h 32m

Jacksonville Albert J Ellis

Tue 12/2

2:26 pm-6:43 pm

1 stop5h 17m

$339

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Mon 11/24

11:19 am-5:59 pm

1 stop5h 40m

Jacksonville Albert J Ellis

Wed 12/3

5:30 am-10:14 am

1 stop5h 44m

$348

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Mon 11/24

9:51 am-5:59 pm

1 stop7h 08m

Jacksonville Albert J Ellis

Thu 12/4

11:53 am-6:43 pm

1 stop7h 50m

$348

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Wed 11/26

4:26 pm-9:58 pm

1 stop4h 32m

Jacksonville Albert J Ellis

Fri 12/5

11:53 am-6:43 pm

1 stop7h 50m

$358

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Wed 11/26

5:00 am-12:53 pm

1 stop6h 53m

Jacksonville Albert J Ellis

Wed 12/3

6:10 am-12:32 pm

1 stop7h 22m

$362

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Tue 11/25

5:23 am-11:16 am

1 stop4h 53m

Jacksonville Albert J Ellis

Tue 12/2

2:26 pm-6:43 pm

1 stop5h 17m

$373

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Tue 3/17

6:00 am-1:39 pm

1 stop6h 39m

Jacksonville Albert J Ellis

Wed 3/18

5:40 am-9:56 am

1 stop5h 16m

$377

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 17 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 October.
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, January is the cheapest month in which you can book a flight from Chicago to Jacksonville, North Carolina (average of $170). Flying from Chicago to Jacksonville, North Carolina in May is currently the most expensive (average of $263). 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 October 30, 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
7.9
Good
7,998 reviews

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Boarding

8.2

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 59m. The distance from Chicago to Jacksonville, North Carolina is about 743 mi.

  • 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 43% 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, January is the cheapest month in which you can book a flight from Chicago to Jacksonville, North Carolina (average of $170). Flying from Chicago to Jacksonville, North Carolina in May is currently the most expensive (average of $263). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Jacksonville

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Charlotte flights
O'Hare Intl to Raleigh flights
Midway to Raleigh flights
O'Hare Intl to Knoxville flights
O'Hare Intl to Asheville flights
Midway to Charlotte flights
O'Hare Intl to Norfolk flights
O'Hare Intl to Myrtle Beach flights
St. Louis to Charlotte flights
O'Hare Intl to Greensboro flights
Midway to Asheville flights
Midway to Knoxville flights
St. Louis to Raleigh flights
Midway to Myrtle Beach flights
Moline to Charlotte flights
Midway to Norfolk flights
St. Louis to Asheville flights
O'Hare Intl to Wilmington flights
St. Louis to Knoxville flights
Moline to Raleigh flights
St. Louis to Norfolk flights
Peoria to Charlotte flights
St. Louis to Myrtle Beach flights
Midway to Wilmington flights
St. Louis to Wilmington flights
Midway to Greensboro flights
O'Hare Intl to Jacksonville flights
Peoria to Raleigh flights
St. Louis to Greensboro flights
Peoria to Greensboro flights
Evansville to Charlotte flights
Moline to Myrtle Beach flights
O'Hare Intl to Blountville flights
O'Hare Intl to Fayetteville flights
Peoria to Knoxville flights
Midway to Jacksonville flights
Midway to Blountville flights
Moline to Knoxville flights
Moline to Wilmington flights
Peoria to Norfolk flights
St. Louis to Fayetteville flights
Bloomington to Raleigh flights
Bloomington to Charlotte flights
Bloomington to Knoxville flights
O'Hare Intl to Greenville flights
Moline to Norfolk flights
O'Hare Intl to New Bern flights
Moline to Jacksonville flights
Peoria to Myrtle Beach flights

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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$256Average$456FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.