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$194+ Cheap flights from Jacksonville, NC (OAJ) to Chicago (CHI)

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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Jacksonville to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Jacksonville (OAJ) to Chicago (CHI). 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)

One-way from

$194
(American Airlines)
From Jacksonville Albert J Ellis to Chicago (CHI)
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One-way flight from Jacksonville Albert J Ellis to Chicago (CHI)
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Find flight deals from Jacksonville to Chicago

Cheapest flights from Jacksonville to Chicago
Explore the most affordable flight options available from Jacksonville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

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 10/236:53 pmOAJ - ORD
1 stop6h 05mDelta
Sat 10/255:20 amORD - OAJ
1 stop4h 53mDelta
Deal found 9/12$257
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.
Tue 10/214:30 pmOAJ - MDW
1 stop6h 44mDelta
Sat 10/256:00 amMDW - OAJ
1 stop4h 13mDelta
Deal found 9/12$257
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.
Tue 10/215:48 amOAJ - ORD
2 stops14h 37mDelta
Sat 10/259:39 amORD - OAJ
1 stop5h 04mDelta
Deal found 9/12$305
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.
Fri 10/246:19 amOAJ - ORD
1 stop4h 11mAmerican Airlines
Sat 10/2511:55 amORD - OAJ
2 stops6h 28mAmerican Airlines
Deal found 9/12$313
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.
Tue 10/217:24 pmOAJ - ORD
1 stop4h 30mAmerican Airlines
Sat 10/255:20 amORD - OAJ
1 stop6h 56mAmerican Airlines
Deal found 9/12$327
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.
Wed 10/225:48 amOAJ - MDW
2 stops12h 55mDelta
Sat 10/256:00 amMDW - OAJ
1 stop4h 13mDelta
Deal found 9/12$331
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 10/237:49 pmOAJ - ORD
1 stop5h 04mAmerican Airlines
Sat 10/256:45 amORD - OAJ
2 stops6h 38mAmerican Airlines
Deal found 9/12$332
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/86:19 amOAJ - ORD
1 stop5h 13mAmerican Airlines
Sat 10/115:20 amORD - OAJ
1 stop6h 56mAmerican Airlines
Deal found 9/14$387
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/172:21 pmOAJ - ORD
1 stop4h 09mAmerican Airlines
Sat 9/205:00 amORD - OAJ
1 stop5h 06mAmerican Airlines
Deal found 9/14$395
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.
Tue 9/305:52 amOAJ - MDW
1 stop4h 48mDelta
Sat 10/44:25 pmMDW - OAJ
1 stop4h 23mDelta
Deal found 9/15$395
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.
Sat 10/255:48 amOAJ - MDW
1 stop4h 52mDelta
Sat 10/254:23 pmMDW - OAJ
1 stop5h 20mDelta
Deal found 9/12$399
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/32:21 pmOAJ - ORD
1 stop5h 13mAmerican Airlines
Tue 10/77:10 amORD - OAJ
1 stop5h 50mAmerican Airlines
Deal found 9/14$427

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jacksonville to Chicago 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 Jacksonville to Chicago that are best for you.

Fly from

Jacksonville

Fly to

Chicago

Route

Depart

Return

Price

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Thu 10/23

6:53 pm-11:58 pm

1 stop6h 05m

Chicago O'Hare Intl

Sat 10/25

5:20 am-11:13 am

1 stop4h 53m

$257

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Fri 10/24

3:01 pm-6:49 pm

1 stop4h 48m

Chicago O'Hare Intl

Sat 10/25

5:20 am-11:13 am

1 stop4h 53m

$257

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Tue 10/21

4:30 pm-10:14 pm

1 stop6h 44m

Chicago Midway

Sat 10/25

6:00 am-11:13 am

1 stop4h 13m

$257

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 10/23

6:53 pm-10:14 pm

1 stop4h 21m

Chicago Midway

Sat 10/25

6:00 am-11:13 am

1 stop4h 13m

$257

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Wed 10/22

11:53 am-4:09 pm

1 stop5h 16m

Chicago Midway

Sat 10/25

10:35 am-3:43 pm

1 stop4h 08m

$257

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Fri 10/24

6:53 pm-10:14 pm

1 stop4h 21m

Chicago Midway

Sat 10/25

6:00 am-11:13 am

1 stop4h 13m

$257

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Wed 10/22

11:53 am-10:26 pm

2 stops11h 33m

Chicago O'Hare Intl

Sat 10/25

5:20 am-11:13 am

1 stop4h 53m

$305

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Tue 10/21

5:48 am-7:25 pm

2 stops14h 37m

Chicago O'Hare Intl

Sat 10/25

9:39 am-3:43 pm

1 stop5h 04m

$305

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Fri 10/24

6:19 am-9:30 am

1 stop4h 11m

Chicago O'Hare Intl

Sat 10/25

11:55 am-7:23 pm

2 stops6h 28m

$313

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Tue 10/21

7:24 pm-10:54 pm

1 stop4h 30m

Chicago O'Hare Intl

Sat 10/25

5:20 am-1:16 pm

1 stop6h 56m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 22 results
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Best time to book a flight from Jacksonville to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Jacksonville 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 Jacksonville to Chicago

What is the cheapest month to book a flight from Jacksonville, North Carolina to Chicago?

Currently, August is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Chicago (average of $245). Flying from Jacksonville, North Carolina to Chicago in March is currently the most expensive (average of $321). 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.

What is the cheapest time of day to fly from OAJ to CHI?

Find hourly flight availability from Jacksonville to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

When flying from Jacksonville, North Carolina to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Jacksonville to Chicago. 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 from for flights from Jacksonville to Chicago?

    Jacksonville Albert J Ellis (OAJ) is the airport you will fly out of if you book a flight from Jacksonville to Chicago. You should not have trouble finding flights to Chicago from Albert J Ellis; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 1 airline has flights from the Jacksonville airport to Chicago. It is only a 11.3 mi journey to Albert J Ellis (OAJ) from Jacksonville’s city center.

  • How long is the flight from Jacksonville, North Carolina to Chicago?

    There are many flights that can get you from Jacksonville, North Carolina to Chicago in 4h 11m. Fly via Delta or American Airlines to get the fastest option. Airlines will cover a distance of 743 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Jacksonville, North Carolina to Chicago round-trip?

    According to our current data, American Airlines ($336), offers the cheapest pricing from Jacksonville, North Carolina to Chicago.

  • Can I find deals for flights from Jacksonville to Chicago that include hotel bookings?

    Yes. In addition to deals on Jacksonville to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Jacksonville to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Jacksonville to Chicago.

  • Can I find deals for business class flights from Jacksonville to Chicago?

    Yes. Cheapflights offers flight deals from Jacksonville to Chicago 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 Jacksonville, North Carolina to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Chicago (average of $245). Flying from Jacksonville, North Carolina to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Jacksonville to Chicago

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Top airline flying from Jacksonville to Chicago

Discover the top airline that operate flights from Jacksonville to Chicago. 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$336Average$440FlexibilityNo cancel feeOn-time71%

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