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$357+ Cheap flights from Jacksonville, NC (OAJ) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — CHI
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$402
(Delta)

Popular in

November

Cheapest in

September

Average price

$518
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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Highest demand for flights based on searches. 2% potential increase in price ($12 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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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 March 28, 2025.

This Delta deal was found by Cheapflights users on 3/26. 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 4/195:30 pmOAJ - ORD
1 stop7h 29mDelta
Wed 4/235:34 pmORD - OAJ
1 stop4h 20mDelta
Deal found 3/26$357
This Delta deal was found by Cheapflights users on 3/27. 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 4/3012:35 pmOAJ - MDW
1 stop4h 37mDelta
Sun 5/46:04 amMDW - OAJ
1 stop6h 37mDelta
Deal found 3/27$402
This American Airlines deal was found by Cheapflights users on 3/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/305:11 amOAJ - ORD
2 stops6h 26mAmerican Airlines
Sun 5/47:00 amORD - OAJ
1 stop4h 36mAmerican Airlines
Deal found 3/27$407

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 March 28, 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

Wed 4/30

2:22 pm-8:50 pm

1 stop7h 28m

Chicago O'Hare Intl

Sun 5/4

5:30 am-11:52 am

1 stop5h 22m

$402

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Wed 4/30

12:35 pm-4:12 pm

1 stop4h 37m

Chicago Midway

Sun 5/4

6:04 am-1:41 pm

1 stop6h 37m

$402

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Wed 4/30

5:11 am-10:37 am

2 stops6h 26m

Chicago O'Hare Intl

Sun 5/4

7:00 am-12:36 pm

1 stop4h 36m

$407

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jacksonville, North Carolina-Chicago flight deals on Cheapflights vs. FlightHub >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 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 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, 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 $323). 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 March 28, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated March 28, 2025.
Get a feel of what it's like to fly with Delta and American Airlines from Jacksonville to Chicago by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,896 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,896 reviews

Crew

8.5

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • What are the cheapest airlines flying from Jacksonville, North Carolina to Chicago round-trip?

    According to our current data, Delta ($402), and American Airlines ($407) offers the cheapest pricing from Jacksonville, North Carolina to Chicago. These flights start at 18% lower than the current average price 3 months from now.

  • 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 $323). 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 Jacksonville?

Book flights to Jacksonville if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$284Average$447FlexibilityNo cancel feeOn-time71%
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