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$189+ 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 3/21. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$339
(Delta)

One-way from

$189
(Delta)
Provider with most accurate pricing for Jacksonville Albert J Ellis-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Jacksonville Albert J Ellis-Chicago (CHI) flights.
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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 October 30, 2025.

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.
Wed 10/2911:53 amOAJ - ORD
1 stop5h 48mDelta
Sat 11/19:39 amORD - OAJ
1 stop5h 04mDelta
Deal found 10/28$435
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.
Thu 10/306:19 amOAJ - ORD
1 stop4h 11mAmerican Airlines
Sat 11/15:20 amORD - OAJ
1 stop6h 56mAmerican Airlines
Deal found 10/28$460
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 11/135:30 amOAJ - ORD
1 stop5h 49mDelta
Mon 11/176:45 amORD - OAJ
1 stop6h 01mDelta
Deal found 10/29$487
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 11/135:30 amOAJ - MDW
1 stop7h 22mDelta
Mon 11/176:00 amMDW - OAJ
1 stop4h 16mDelta
Deal found 10/29$487
This Delta deal was found by Cheapflights users on 10/30. 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.
Sat 12/276:42 pmOAJ - ORD
1 stop6h 20mDelta
Thu 1/15:30 amORD - OAJ
1 stop6h 25mDelta
Deal found 10/30$494
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.
Tue 10/287:24 pmOAJ - ORD
1 stop4h 30mAmerican Airlines
Sat 11/14:56 pmORD - OAJ
1 stop4h 25mAmerican Airlines
Deal found 10/28$505
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 11/611:53 amOAJ - ORD
1 stop5h 48mDelta
Sun 11/95:23 amORD - OAJ
1 stop4h 53mDelta
Deal found 10/29$525
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.
Fri 11/74:30 pmOAJ - MDW
1 stop6h 44mDelta
Tue 11/116:00 amMDW - OAJ
1 stop6h 46mDelta
Deal found 10/29$525
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:00 amOAJ - ORD
2 stops6h 58mAmerican Airlines
Sun 11/95:30 pmORD - OAJ
1 stop5h 41mAmerican Airlines
Deal found 10/29$530
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:00 amOAJ - ORD
2 stops6h 58mAmerican Airlines
Mon 11/1710:15 amORD - OAJ
2 stops7h 16mAmerican Airlines
Deal found 10/29$535
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:55 pmOAJ - ORD
1 stop5h 04mAmerican Airlines
Sat 1/36:38 pmORD - OAJ
1 stop4h 21mAmerican Airlines
Deal found 10/29$564
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/247:02 pmOAJ - ORD
1 stop5h 35mAmerican Airlines
Sat 11/296:35 pmORD - OAJ
1 stop4h 36mAmerican Airlines
Deal found 10/29$587

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 October 30, 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 - MDW

OAJMDW

Jacksonville Albert J Ellis

Tue 3/24

5:40 am-9:56 am

1 stop5h 16m

Chicago Midway

Sat 3/28

4:30 pm-10:14 pm

1 stop4h 44m

$339

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Wed 3/25

6:25 pm-11:54 pm

1 stop6h 29m

Chicago O'Hare Intl

Sat 3/28

2:45 pm-10:14 pm

1 stop6h 29m

$358

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 11/13

5:30 am-11:52 am

1 stop7h 22m

Chicago Midway

Mon 11/17

6:00 am-11:16 am

1 stop4h 16m

$487

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Sat 12/27

6:42 pm-12:02 am

1 stop6h 20m

Chicago O'Hare Intl

Thu 1/1

5:30 am-12:55 pm

1 stop6h 25m

$494

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Thu 11/13

5:00 am-10:58 am

2 stops6h 58m

Chicago O'Hare Intl

Mon 11/17

3:44 pm-11:02 pm

1 stop6h 18m

$530

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Mon 11/24

7:02 pm-11:37 pm

1 stop5h 35m

Chicago O'Hare Intl

Sat 11/29

6:35 pm-12:11 am

1 stop4h 36m

$587

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Mon 12/22

6:42 pm-12:02 am

1 stop6h 20m

Chicago O'Hare Intl

Tue 12/23

10:00 am-6:02 pm

1 stop7h 02m

$638

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Wed 11/26

5:00 am-9:05 am

1 stop5h 05m

Chicago O'Hare Intl

Sat 11/29

5:00 am-10:33 am

1 stop4h 33m

$648

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 12/20

6:42 pm-10:22 pm

1 stop4h 40m

Chicago Midway

Sat 1/3

4:25 pm-9:36 pm

1 stop4h 11m

$709

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Mon 11/24

6:44 pm-11:40 pm

1 stop5h 56m

Chicago Midway

Sun 11/30

6:00 am-11:10 am

1 stop4h 10m

$727

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 15 results
1
2

Compare providers for flights from Jacksonville to Chicago

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 Jacksonville to Chicago 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 Jacksonville, North Carolina-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Jacksonville, North Carolina-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Jacksonville, North Carolina-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Jacksonville, North Carolina-Chicago 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 Jacksonville, North Carolina-Chicago 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 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, September is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Chicago (average of $182). Flying from Jacksonville, North Carolina to Chicago in April is currently the most expensive (average of $268). 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 October 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Jacksonville, North Carolina to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 31% on your trip compared to booking a flight in the evening.

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 5h 16m. Fly via Delta to get the fastest option. Airlines will cover a distance of 729 mi.

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

    According to our current data, American Airlines ($356), 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, September is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Chicago (average of $182). Flying from Jacksonville, North Carolina to Chicago in April is currently the most expensive (average of $268). 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
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Hammond
Porter
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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$356Average$440FlexibilityNo cancel feeOn-time71%

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