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$240+ 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 3/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAJ
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
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 February 3, 2026.

This Delta deal was found by Cheapflights users on 2/2. 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 3/117:10 am
ORD
-
OAJ
1 stop5h 30m
Delta
Wed 3/182:21 pm
OAJ
-
ORD
1 stop5h 32m
Delta
Deal found 2/2$311
This Delta deal was found by Cheapflights users on 2/2. 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 5/99:10 am
ORD
-
OAJ
1 stop5h 17m
Delta
Mon 5/116:47 pm
OAJ
-
ORD
1 stop6h 12m
Delta
Deal found 2/2$339
This Delta deal was found by Cheapflights users on 2/2. 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 5/65:10 am
ORD
-
OAJ
1 stop5h 08m
Delta
Sun 5/106:47 pm
OAJ
-
ORD
1 stop6h 12m
Delta
Deal found 2/2$344
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:00 am
MDW
-
OAJ
1 stop4h 18m
Delta
Sun 4/266:49 pm
OAJ
-
MDW
1 stop4h 39m
Delta
Deal found 1/31$357
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/245:10 am
ORD
-
OAJ
1 stop5h 08m
Delta
Sun 4/265:40 am
OAJ
-
ORD
1 stop5h 29m
Delta
Deal found 1/31$357
This Delta deal was found by Cheapflights users on 2/2. 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 5/78:10 am
ORD
-
OAJ
1 stop6h 17m
Delta
Sun 5/106:47 pm
OAJ
-
ORD
1 stop6h 12m
Delta
Deal found 2/2$358
This Delta deal was found by Cheapflights users on 2/2. 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 5/88:10 am
ORD
-
OAJ
1 stop6h 17m
Delta
Sun 5/104:07 pm
OAJ
-
ORD
1 stop5h 18m
Delta
Deal found 2/2$377
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:14 am
ORD
-
OAJ
1 stop5h 26m
Delta
Sun 4/265:40 am
OAJ
-
ORD
1 stop5h 29m
Delta
Deal found 1/31$398
This Delta deal was found by Cheapflights users on 2/1. 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 2/186:45 am
ORD
-
OAJ
1 stop7h 02m
Delta
Wed 2/2511:48 am
OAJ
-
ORD
1 stop6h 03m
Delta
Deal found 2/1$421
This American Airlines deal was found by Cheapflights users on 2/2. 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 2/186:08 am
ORD
-
OAJ
2 stops6h 30m
American Airlines
Wed 2/252:03 pm
OAJ
-
ORD
1 stop4h 55m
American Airlines
Deal found 2/2$426
This Delta deal was found by Cheapflights users on 2/1. 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 2/176:00 am
MDW
-
OAJ
1 stop4h 07m
Delta
Sat 2/214:00 pm
OAJ
-
MDW
1 stop7h 31m
Delta
Deal found 2/1$435
This Delta deal was found by Cheapflights users on 2/2. 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 2/75:30 am
ORD
-
OAJ
1 stop4h 34m
Delta
Wed 2/115:40 am
OAJ
-
ORD
1 stop5h 25m
Delta
Deal found 2/2$435

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 February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$311
(Delta)

One-way from

$240
(Delta)
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

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 February 3, 2026.
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

Wed 3/11

7:10 am-1:40 pm

1 stop5h 30m

Jacksonville Albert J Ellis

Wed 3/18

11:58 am-4:49 pm

1 stop5h 51m

$311

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Fri 4/24

6:00 am-1:40 pm

1 stop6h 40m

Jacksonville Albert J Ellis

Sun 4/26

5:40 am-9:56 am

1 stop5h 16m

$357

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Thu 4/23

6:00 am-11:18 am

1 stop4h 18m

Jacksonville Albert J Ellis

Sun 4/26

6:49 pm-10:28 pm

1 stop4h 39m

$357

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Fri 4/24

5:10 am-11:18 am

1 stop5h 08m

Jacksonville Albert J Ellis

Sun 4/26

5:40 am-10:09 am

1 stop5h 29m

$357

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Thu 4/23

7:14 am-1:40 pm

1 stop5h 26m

Jacksonville Albert J Ellis

Sun 4/26

5:40 am-10:09 am

1 stop5h 29m

$398

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Wed 2/18

2:46 pm-10:35 pm

1 stop6h 49m

Jacksonville Albert J Ellis

Wed 2/25

11:48 am-4:51 pm

1 stop6h 03m

$421

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Tue 2/17

6:00 am-11:07 am

1 stop4h 07m

Jacksonville Albert J Ellis

Sat 2/21

4:00 pm-10:31 pm

1 stop7h 31m

$435

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Tue 2/17

5:25 am-11:07 am

1 stop4h 42m

Jacksonville Albert J Ellis

Sat 2/21

5:36 am-10:17 am

1 stop5h 41m

$435

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Sat 2/7

5:30 am-11:04 am

1 stop4h 34m

Jacksonville Albert J Ellis

Wed 2/11

5:40 am-10:05 am

1 stop5h 25m

$435

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Tue 2/17

3:16 pm-10:57 pm

1 stop6h 41m

Jacksonville Albert J Ellis

Sat 2/21

4:11 pm-10:46 pm

2 stops7h 35m

$466

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 18 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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Jacksonville, North Carolina flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, August is the cheapest month in which you can book a flight from Chicago to Jacksonville, North Carolina (average of $198). Flying from Chicago to Jacksonville, North Carolina in November is currently the most expensive (average of $306). 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.

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 5h 30m. 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.

  • 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 $198). Flying from Chicago to Jacksonville, North Carolina in November is currently the most expensive (average of $306). 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.
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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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$256Average$456FlexibilityNo cancel feeOn-time71%

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