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$159+ 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 8/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAJ
Jul 24 — Jul 311
Fri 7/24
Fri 7/31
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 June 24, 2026.

This Delta deal was found by Cheapflights users on 6/22. 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 8/56:05 am
MDW
-
OAJ
1 stop4h 25m
Delta
Sun 8/96:48 pm
OAJ
-
MDW
1 stop4h 48m
Delta
Deal found 6/22$367
This American Airlines deal was found by Cheapflights users on 6/22. 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 8/58:54 am
ORD
-
OAJ
1 stop6h 51m
American Airlines
Sun 8/98:04 pm
OAJ
-
ORD
1 stop4h 52m
American Airlines
Deal found 6/22$367
This Delta deal was found by Cheapflights users on 6/20. 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 8/271:50 pm
ORD
-
OAJ
1 stop7h 39m
Delta
Sun 8/302:27 pm
OAJ
-
ORD
1 stop7h 28m
Delta
Deal found 6/20$383
This American Airlines deal was found by Cheapflights users on 6/22. 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.
Tue 7/74:45 pm
ORD
-
OAJ
1 stop4h 31m
American Airlines
Sat 7/118:53 am
OAJ
-
ORD
1 stop6h 27m
American Airlines
Deal found 6/22$475
This Delta deal was found by Cheapflights users on 6/22. 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 7/75:30 am
ORD
-
OAJ
1 stop4h 49m
Delta
Sat 7/1112:11 pm
OAJ
-
ORD
2 stops10h 41m
Delta
Deal found 6/22$480
This Delta deal was found by Cheapflights users on 6/20. 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 8/276:05 am
MDW
-
OAJ
1 stop6h 41m
Delta
Sun 8/306:00 am
OAJ
-
MDW
1 stop4h 59m
Delta
Deal found 6/20$493
This Delta deal was found by Cheapflights users on 6/22. 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 6/295:30 am
ORD
-
OAJ
1 stop4h 51m
Delta
Mon 7/136:44 pm
OAJ
-
ORD
1 stop6h 09m
Delta
Deal found 6/22$526
This Delta deal was found by Cheapflights users on 6/24. 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 7/912:41 pm
MDW
-
OAJ
1 stop4h 21m
Delta
Mon 7/134:43 pm
OAJ
-
MDW
1 stop6h 32m
Delta
Deal found 6/24$527
This American Airlines deal was found by Cheapflights users on 6/24. 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 7/98:00 am
ORD
-
OAJ
1 stop5h 32m
American Airlines
Mon 7/131:14 pm
OAJ
-
ORD
1 stop5h 25m
American Airlines
Deal found 6/24$527
This American Airlines deal was found by Cheapflights users on 6/20. 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.
Sat 6/276:29 am
ORD
-
OAJ
1 stop7h 06m
American Airlines
Sun 6/283:07 pm
OAJ
-
ORD
1 stop5h 38m
American Airlines
Deal found 6/20$569
This American Airlines deal was found by Cheapflights users on 6/24. 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.
Mon 6/295:10 am
ORD
-
OAJ
1 stop6h 39m
American Airlines
Mon 7/131:14 pm
OAJ
-
ORD
1 stop7h 37m
American Airlines
Deal found 6/24$577
This American Airlines deal was found by Cheapflights users on 6/21. 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 7/34:45 pm
ORD
-
OAJ
1 stop4h 31m
American Airlines
Sun 7/58:53 am
OAJ
-
ORD
1 stop6h 27m
American Airlines
Deal found 6/21$636

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 June 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$367
(Delta)

One-way from

$159
(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 June 24, 2026.
Use the filters below to find and compare flights from Chicago to Jacksonville that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Wed 8/5

6:05 am-11:30 am

1 stop4h 25m

Jacksonville Albert J Ellis

Sun 8/9

6:48 pm-10:36 pm

1 stop4h 48m

$367

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Wed 8/5

8:54 am-4:45 pm

1 stop6h 51m

Jacksonville Albert J Ellis

Sun 8/9

8:04 pm-11:56 pm

1 stop4h 52m

$367

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Thu 8/27

1:50 pm-10:29 pm

1 stop7h 39m

Jacksonville Albert J Ellis

Sun 8/30

2:27 pm-8:55 pm

1 stop7h 28m

$383

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Tue 7/7

5:30 am-11:19 am

1 stop4h 49m

Jacksonville Albert J Ellis

Sat 7/11

12:11 pm-9:52 pm

2 stops10h 41m

$480

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Thu 8/27

1:27 pm-10:29 pm

2 stops8h 02m

Jacksonville Albert J Ellis

Sun 8/30

12:10 pm-4:15 pm

1 stop5h 05m

$498

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Thu 7/9

8:00 am-2:32 pm

1 stop5h 32m

Jacksonville Albert J Ellis

Mon 7/13

1:14 pm-5:39 pm

1 stop5h 25m

$527

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Thu 7/9

12:41 pm-6:02 pm

1 stop4h 21m

Jacksonville Albert J Ellis

Mon 7/13

4:43 pm-10:15 pm

1 stop6h 32m

$527

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Mon 7/6

5:30 am-11:21 am

1 stop4h 51m

Jacksonville Albert J Ellis

Fri 7/10

6:44 pm-11:53 pm

1 stop6h 09m

$569

ChicagoJacksonville

ORD - OAJ

ORDOAJ

Chicago O'Hare Intl

Thu 7/9

6:30 am-6:02 pm

2 stops10h 32m

Jacksonville Albert J Ellis

Mon 7/13

4:43 pm-8:33 pm

1 stop4h 50m

$682

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Tue 7/7

6:00 am-11:19 am

1 stop4h 19m

Jacksonville Albert J Ellis

Sat 7/11

7:00 am-5:52 pm

2 stops11h 52m

$812

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/23

Showing 1-10 of 24 resultsSorted by cheapest first
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3

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 June.
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
No data available for this route at this time. Please check back soon.

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 25m. The distance from Chicago to Jacksonville, North Carolina is about 729 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.

  • 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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 June 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$256Average$528FlexibilityNo cancel feeOn-time71%

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