HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$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
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Jacksonville to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/15. 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 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 1/35:00 amORD - OAJ
1 stop4h 19mAmerican Airlines
Deal found 12/15$1,002

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$313
(Delta)

One-way from

$189
(Delta)
Provider with most accurate pricing for Jacksonville Albert J Ellis-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jacksonville Albert J Ellis-Chicago (CHI) flights.
Search Deals
From Jacksonville Albert J Ellis to Chicago (CHI)
Search Deals
One-way flight from Jacksonville Albert J Ellis to Chicago (CHI)
Search Deals

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 December 18, 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 1/14

11:44 am-4:45 pm

1 stop6h 01m

Chicago O'Hare Intl

Wed 1/21

5:30 am-11:04 am

1 stop4h 34m

$313

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Wed 1/14

1:57 pm-8:15 pm

2 stops7h 18m

Chicago O'Hare Intl

Wed 1/21

10:10 am-3:00 pm

1 stop3h 50m

$318

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Thu 1/1

5:00 am-9:21 am

1 stop5h 21m

Chicago O'Hare Intl

Mon 1/5

5:00 am-12:27 pm

1 stop6h 27m

$432

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Sun 3/22

2:20 pm-6:46 pm

1 stop5h 26m

Chicago O'Hare Intl

Sat 3/28

9:43 am-3:09 pm

1 stop4h 26m

$508

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Sun 3/22

5:00 am-9:05 am

1 stop5h 05m

Chicago O'Hare Intl

Sun 3/22

1:39 pm-7:26 pm

1 stop4h 47m

$693

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Sun 3/22

5:00 am-9:05 am

1 stop5h 05m

Chicago O'Hare Intl

Sat 3/28

4:14 pm-11:55 pm

2 stops6h 41m

$762

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Tue 1/20

11:44 am-4:55 pm

1 stop6h 11m

Chicago O'Hare Intl

Sat 1/24

5:30 am-11:04 am

1 stop4h 34m

$954

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 1/1

5:35 am-9:05 am

1 stop4h 30m

Chicago Midway

Mon 1/5

1:28 pm-10:37 pm

2 stops8h 09m

$1,231

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Sat 3/21

11:50 am-4:49 pm

1 stop5h 59m

$189

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Sat 3/21

10:58 am-5:17 pm

2 stops7h 19m

$314

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 14 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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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, October is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Chicago (average of $180). Flying from Jacksonville, North Carolina to Chicago in December is currently the most expensive (average of $290). 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 December 18, 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 6h 01m. 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 ($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, October is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Chicago (average of $180). Flying from Jacksonville, North Carolina to Chicago in December is currently the most expensive (average of $290). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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 Jacksonville to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Charlotte to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Norfolk to O'Hare Intl flights
Raleigh to Midway flights
Charlotte to Midway flights
Greensboro to O'Hare Intl flights
Norfolk to Midway flights
Charlotte to St. Louis flights
Raleigh to St. Louis flights
Knoxville to O'Hare Intl flights
Asheville to O'Hare Intl flights
Knoxville to Midway flights
Myrtle Beach to O'Hare Intl flights
Greensboro to Midway flights
Wilmington to O'Hare Intl flights
Wilmington to Midway flights
Myrtle Beach to Midway flights
Asheville to Midway flights
Greensboro to St. Louis flights
Myrtle Beach to St. Louis flights
Raleigh to Peoria flights
Wilmington to St. Louis flights
Blountville to O'Hare Intl flights
Knoxville to St. Louis flights
Raleigh to Moline flights
Raleigh to Evansville flights
Asheville to St. Louis flights
Norfolk to St. Louis flights
Norfolk to Peoria flights
Knoxville to Peoria flights
Charlotte to Evansville flights
Wilmington to Peoria flights
Fayetteville to St. Louis flights
Charlotte to Peoria flights
Norfolk to Moline flights
New Bern to O'Hare Intl flights
Raleigh to Dubuque flights
Fayetteville to O'Hare Intl flights
Greensboro to Peoria flights
Myrtle Beach to Peoria flights
Jacksonville to O'Hare Intl flights
Wilmington to Moline flights
Fayetteville to Moline flights
Blountville to St. Louis flights
Asheville to Peoria flights
Asheville to Moline flights
Blountville to Midway flights
Myrtle Beach to Moline flights
Charlotte to Bloomington flights

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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$356Average$440FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.