$358+ 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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — CHI
Dec 15 — Dec 221
Round-trip
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
Best
Last-minute
One-way
Cheapest flights from Jacksonville to ChicagoExplore 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 November 15, 2026.
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 November 15, 2026.
This Delta deal was found by Cheapflights users on 11/13. 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 12/166:35 pm -
1 stop6h 21m
Tue 1/59:50 am -
1 stop5h 55m
Deal found 11/13![Delta logo]()
$449
This American Airlines deal was found by Cheapflights users on 11/11. 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 11/248:24 pm -
1 stop4h 35m
Wed 12/211:47 am -
1 stop5h 58m
Deal found 11/11![American Airlines logo]()
$488
This Delta deal was found by Cheapflights users on 11/10. 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 11/246:00 am -
1 stop7h 20m
Wed 12/28:04 am -
1 stop4h 38m
Deal found 11/10![Delta logo]()
$531
This Delta deal was found by Cheapflights users on 11/10. 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 11/262:30 pm -
1 stop5h 35m
Thu 12/35:30 am -
1 stop7h 12m
Deal found 11/10![Delta logo]()
$557
This American Airlines deal was found by Cheapflights users on 11/12. 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 11/278:24 pm -
1 stop4h 35m
Tue 12/14:58 pm -
1 stop4h 31m
Deal found 11/12![American Airlines logo]()
$587
This Delta deal was found by Cheapflights users on 11/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/144:13 pm -
1 stop5h 36m
Mon 11/165:30 am -
1 stop4h 46m
Deal found 11/14![Delta logo]()
$600
This American Airlines deal was found by Cheapflights users on 11/12. 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 11/208:52 am -
1 stop4h 34m
Mon 11/234:58 pm -
1 stop4h 31m
Deal found 11/12![American Airlines logo]()
$645
Best flights from Jacksonville to ChicagoDiscover carefully curated flight deals from Jacksonville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 15, 2026.
Discover carefully curated flight deals from Jacksonville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 15, 2026.
This Delta deal was found by Cheapflights users on 11/13. 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 12/166:35 pm -
1 stop6h 21m
Tue 1/59:50 am -
1 stop5h 55m
Deal found 11/13![Delta logo]()
$449
This American Airlines deal was found by Cheapflights users on 11/11. 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 11/248:24 pm -
1 stop4h 35m
Wed 12/211:47 am -
1 stop5h 58m
Deal found 11/11![American Airlines logo]()
$488
This Delta deal was found by Cheapflights users on 11/11. 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 11/242:26 pm -
1 stop5h 39m
Wed 12/211:35 am -
2 stops9h 53m
Deal found 11/11![Delta logo]()
$536
This Delta deal was found by Cheapflights users on 11/10. 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 11/262:30 pm -
1 stop5h 35m
Thu 12/35:30 am -
1 stop7h 12m
Deal found 11/10![Delta logo]()
$557
This American Airlines deal was found by Cheapflights users on 11/12. 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 11/208:52 am -
1 stop4h 34m
Mon 11/234:58 pm -
1 stop4h 31m
Deal found 11/12![American Airlines logo]()
$645
This Delta deal was found by Cheapflights users on 11/12. 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.
Fri 11/2011:56 am -
2 stops10h 37m
Mon 11/238:04 am -
1 stop4h 38m
Deal found 11/12![Delta logo]()
$700
This Delta deal was found by Cheapflights users on 11/12. 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.
Fri 11/272:30 pm -
1 stop5h 35m
Tue 12/111:35 am -
2 stops9h 53m
Deal found 11/12![Delta logo]()
$732
This Delta deal was found by Cheapflights users on 11/10. 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 12/211:59 am -
2 stops10h 37m
Fri 12/411:35 am -
1 stop5h 17m
Deal found 11/10![Delta logo]()
$780
Last-minute flights from Jacksonville to ChicagoDiscover last-minute flight deals from Jacksonville to Chicago. Data last updated November 15, 2026 and is based on user searches.
Discover last-minute flight deals from Jacksonville to Chicago. Data last updated November 15, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 11/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/144:13 pm -
1 stop5h 36m
Mon 11/165:30 am -
1 stop4h 46m
Deal found 11/14![Delta logo]()
$600
This American Airlines deal was found by Cheapflights users on 11/12. 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 11/208:52 am -
1 stop4h 34m
Mon 11/234:58 pm -
1 stop4h 31m
Deal found 11/12![American Airlines logo]()
$645
This American Airlines deal was found by Cheapflights users on 11/11. 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 11/248:24 pm -
1 stop4h 35m
Wed 12/211:47 am -
1 stop5h 58m
Deal found 11/11![American Airlines logo]()
$488
This Delta deal was found by Cheapflights users on 11/10. 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 11/246:00 am -
1 stop7h 20m
Wed 12/28:04 am -
1 stop4h 38m
Deal found 11/10![Delta logo]()
$531
This Delta deal was found by Cheapflights users on 11/10. 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 11/262:30 pm -
1 stop5h 35m
Thu 12/35:30 am -
1 stop7h 12m
Deal found 11/10![Delta logo]()
$557
This American Airlines deal was found by Cheapflights users on 11/12. 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 11/278:24 pm -
1 stop4h 35m
Tue 12/14:58 pm -
1 stop4h 31m
Deal found 11/12![American Airlines logo]()
$587
This Delta deal was found by Cheapflights users on 11/13. 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 12/166:35 pm -
1 stop6h 21m
Tue 1/59:50 am -
1 stop5h 55m
Deal found 11/13![Delta logo]()
$449
One-way flights from Jacksonville to ChicagoSearch for one-way flight options from Jacksonville to Chicago. Find affordable one-way fares based on user searches. Data last updated November 15, 2026.
Search for one-way flight options from Jacksonville to Chicago. Find affordable one-way fares based on user searches. Data last updated November 15, 2026.
This Delta deal was found by Cheapflights users on 11/11. 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 12/172:23 pm -
1 stop5h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![Delta logo]()
$358
This American Airlines deal was found by Cheapflights users on 11/14. 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.
Mon 11/301:14 pm -
1 stop5h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/14![American Airlines logo]()
$423
This Delta deal was found by Cheapflights users on 11/10. 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.
Sun 12/206:10 am -
2 stops11h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Delta logo]()
$555
This Delta deal was found by Cheapflights users on 11/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:00 am -
2 stops8h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/14![Delta logo]()
$615
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 November 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $449 (Delta) |
One-way from | $358 (Delta) |
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 7,457,451 searches. Data last updated November 15, 2026.
Use the filters below to find and compare flights from Jacksonville to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - ORD Chicago O'Hare Intl
OAJORD
Jacksonville Albert J Ellis
Thu 12/17
2:23 pm-7:09 pm
1 stop5h 46m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$358
Quickest round-trip
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - ORD Chicago O'Hare Intl
OAJORD
Jacksonville Albert J Ellis
Sun 12/20
7:00 am-11:00 am
1 stop5h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$358
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - ORD Chicago O'Hare Intl
OAJORD
Jacksonville Albert J Ellis
Mon 11/30
1:14 pm-5:44 pm
1 stop5h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$423
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - ORD Chicago O'Hare Intl
OAJORD
Jacksonville Albert J Ellis
Wed 12/16
6:35 pm-11:56 pm
1 stop6h 21m
Chicago O'Hare Intl
Tue 1/5
9:50 am-4:45 pm
1 stop5h 55m
$449
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - ORD Chicago O'Hare Intl
OAJORD
Jacksonville Albert J Ellis
Tue 11/24
8:24 pm-11:59 pm
1 stop4h 35m
Chicago O'Hare Intl
Wed 12/2
11:47 am-6:45 pm
1 stop5h 58m
$488
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - ORD Chicago O'Hare Intl
OAJORD
Jacksonville Albert J Ellis
Tue 11/24
2:26 pm-7:05 pm
1 stop5h 39m
Chicago O'Hare Intl
Wed 12/2
11:35 am-10:28 pm
2 stops9h 53m
$536
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - ORD Chicago O'Hare Intl
OAJORD
Jacksonville Albert J Ellis
Sun 12/20
6:10 am-4:53 pm
2 stops11h 43m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$555
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - ORD Chicago O'Hare Intl
OAJORD
Jacksonville Albert J Ellis
Thu 11/26
2:30 pm-7:05 pm
1 stop5h 35m
Chicago O'Hare Intl
Thu 12/3
5:30 am-1:42 pm
1 stop7h 12m
$557
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - ORD Chicago O'Hare Intl
OAJORD
Jacksonville Albert J Ellis
Mon 11/30
6:00 am-1:59 pm
2 stops8h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$615
JacksonvilleChicago
OAJ Jacksonville Albert J Ellis - ORD Chicago O'Hare Intl
OAJORD
Jacksonville Albert J Ellis
Fri 11/20
8:52 am-12:26 pm
1 stop4h 34m
Chicago O'Hare Intl
Mon 11/23
4:58 pm-10:29 pm
1 stop4h 31m
$645
Showing 1-10 of 13 resultsSorted by cheapest first
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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- 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.
OAJ-CHI
OAJ-ORD
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
OAJ-CHI
OAJ-ORD
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 Jacksonville to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Jacksonville
Popular flights
Top destinations
Alternative routes for Jacksonville to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 15, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Jacksonville to Chicago by cabin class
Find flights from Jacksonville to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Jacksonville and Chicago flights
Browse other Jacksonville and Chicago flight options. Last updated on November 15, 2026.
Other flights from Jacksonville
Browse through other flights departing from Jacksonville. Flights are based on user searches made on Cheapflights and were last updated on November 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Jacksonville to Chicago flights
Consider these flights traveling from Jacksonville to Chicago.
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 7,457,451 searches. Data last updated November 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$397 | Average$660 | FlexibilityNo cancel fee | On-time71% |