$393+ Cheap flights from Chicago (CHI) to Jacksonville, NC (OAJ)
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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAJ
Oct 25 — Nov 11
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Jacksonville 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 Chicago to Jacksonville
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to JacksonvilleExplore the most affordable flight options available from Chicago to Jacksonville. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2026.
Explore the most affordable flight options available from Chicago to Jacksonville. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2026.
This Delta deal was found by Cheapflights users on 9/20. 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 10/171:27 pm -
2 stops7h 55m
Tue 10/206:33 pm -
1 stop5h 00m
Deal found 9/20![Delta logo]()
$458
This Delta deal was found by Cheapflights users on 9/23. 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 10/235:09 pm -
1 stop4h 13m
Fri 10/3012:00 pm -
1 stop5h 14m
Deal found 9/23![Delta logo]()
$477
This American Airlines deal was found by Cheapflights users on 9/20. 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 12/217:59 am -
1 stop7h 12m
Mon 12/284:36 pm -
1 stop7h 24m
Deal found 9/20![American Airlines logo]()
$477
This American Airlines deal was found by Cheapflights users on 9/21. 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 10/179:02 am -
1 stop6h 29m
Tue 10/207:24 pm -
1 stop5h 44m
Deal found 9/21![American Airlines logo]()
$492
This Delta deal was found by Cheapflights users on 9/25. 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 10/177:00 am -
2 stops7h 21m
Tue 10/202:21 pm -
1 stop7h 17m
Deal found 9/25![Delta logo]()
$502
This Delta deal was found by Cheapflights users on 9/23. 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 9/268:05 am -
1 stop6h 17m
Wed 9/3012:00 pm -
2 stops11h 18m
Deal found 9/23![Delta logo]()
$510
This Delta deal was found by Cheapflights users on 9/22. 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 10/76:04 am -
1 stop6h 37m
Sun 10/116:33 pm -
1 stop5h 00m
Deal found 9/22![Delta logo]()
$557
This Delta deal was found by Cheapflights users on 9/23. 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 10/89:51 am -
1 stop7h 02m
Mon 10/122:21 pm -
1 stop7h 17m
Deal found 9/23![Delta logo]()
$557
This American Airlines deal was found by Cheapflights users on 9/20. 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 9/238:05 am -
1 stop4h 22m
Sun 9/276:08 pm -
1 stop6h 51m
Deal found 9/20![American Airlines logo]()
$580
This Delta deal was found by Cheapflights users on 9/21. 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 9/236:00 am -
2 stops10h 54m
Sun 9/2712:00 pm -
1 stop5h 37m
Deal found 9/21![Delta logo]()
$605
Best flights from Chicago to JacksonvilleDiscover carefully curated flight deals from Chicago to Jacksonville that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 25, 2026.
Discover carefully curated flight deals from Chicago to Jacksonville that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 25, 2026.
This American Airlines deal was found by Cheapflights users on 9/20. 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 12/217:59 am -
1 stop7h 12m
Mon 12/284:36 pm -
1 stop7h 24m
Deal found 9/20![American Airlines logo]()
$477
This Delta deal was found by Cheapflights users on 9/24. 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 10/171:27 pm -
2 stops7h 55m
Tue 10/2012:00 pm -
1 stop5h 14m
Deal found 9/24![Delta logo]()
$502
This American Airlines deal was found by Cheapflights users on 9/21. 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 10/179:02 am -
1 stop6h 29m
Tue 10/207:24 pm -
1 stop5h 44m
Deal found 9/21![American Airlines logo]()
$492
This Delta deal was found by Cheapflights users on 9/23. 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 10/177:00 am -
2 stops7h 21m
Tue 10/202:21 pm -
1 stop7h 17m
Deal found 9/23![Delta logo]()
$502
This Delta deal was found by Cheapflights users on 9/22. 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 10/76:04 am -
1 stop6h 37m
Sun 10/116:33 pm -
1 stop5h 00m
Deal found 9/22![Delta logo]()
$557
This Delta deal was found by Cheapflights users on 9/23. 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 10/812:49 pm -
1 stop4h 04m
Mon 10/126:00 am -
2 stops7h 47m
Deal found 9/23![Delta logo]()
$733
Last-minute flights from Chicago to JacksonvilleDiscover last-minute flight deals from Chicago to Jacksonville. Data last updated September 25, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Jacksonville. Data last updated September 25, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/23. 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 9/268:05 am -
1 stop6h 17m
Wed 9/3012:00 pm -
2 stops11h 18m
Deal found 9/23![Delta logo]()
$510
This Delta deal was found by Cheapflights users on 9/22. 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 10/76:04 am -
1 stop6h 37m
Sun 10/116:33 pm -
1 stop5h 00m
Deal found 9/22![Delta logo]()
$557
This Delta deal was found by Cheapflights users on 9/23. 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 10/89:51 am -
1 stop7h 02m
Mon 10/122:21 pm -
1 stop7h 17m
Deal found 9/23![Delta logo]()
$557
This Delta deal was found by Cheapflights users on 9/22. 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 10/155:27 am -
1 stop7h 14m
Sun 10/186:00 am -
1 stop5h 11m
Deal found 9/22![Delta logo]()
$878
This Delta deal was found by Cheapflights users on 9/20. 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 10/171:27 pm -
2 stops7h 55m
Tue 10/206:33 pm -
1 stop5h 00m
Deal found 9/20![Delta logo]()
$458
This American Airlines deal was found by Cheapflights users on 9/21. 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 10/179:02 am -
1 stop6h 29m
Tue 10/207:24 pm -
1 stop5h 44m
Deal found 9/21![American Airlines logo]()
$492
This Delta deal was found by Cheapflights users on 9/25. 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 10/177:00 am -
2 stops7h 21m
Tue 10/202:21 pm -
1 stop7h 17m
Deal found 9/25![Delta logo]()
$502
This Delta deal was found by Cheapflights users on 9/23. 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 10/186:30 am -
1 stop6h 11m
Fri 10/232:21 pm -
1 stop5h 50m
Deal found 9/23![Delta logo]()
$1,005
This Delta deal was found by Cheapflights users on 9/23. 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 10/235:09 pm -
1 stop4h 13m
Fri 10/3012:00 pm -
1 stop5h 14m
Deal found 9/23![Delta logo]()
$477
One-way flights from Chicago to JacksonvilleSearch for one-way flight options from Chicago to Jacksonville. Find affordable one-way fares based on user searches. Data last updated September 25, 2026.
Search for one-way flight options from Chicago to Jacksonville. Find affordable one-way fares based on user searches. Data last updated September 25, 2026.
This American Airlines deal was found by Cheapflights users on 9/21. 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 10/101:17 pm -
1 stop5h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![American Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 9/21. 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 10/106:04 am -
1 stop4h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$403
This Delta deal was found by Cheapflights users on 9/21. 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 10/115:27 am -
1 stop4h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$403
This Delta deal was found by Cheapflights users on 9/21. 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 10/101:55 pm -
2 stops7h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$408
Find flight deals from Chicago to Jacksonville
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Jacksonville (OAJ). 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 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $458 (Delta) |
One-way from | $393 (American Airlines) |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Jacksonville 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 September 25, 2026.
Use the filters below to find and compare flights from Chicago to Jacksonville that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Sat 10/10
6:04 am-11:09 am
1 stop4h 05m
Jacksonville Albert J Ellis
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$403
ChicagoJacksonville
ORD Chicago O'Hare Intl - OAJ Jacksonville Albert J Ellis
ORDOAJ
Chicago O'Hare Intl
Sun 10/11
5:27 am-11:09 am
1 stop4h 42m
Jacksonville Albert J Ellis
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$403
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Sun 10/11
9:29 am-5:53 pm
2 stops7h 24m
Jacksonville Albert J Ellis
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$408
ChicagoJacksonville
ORD Chicago O'Hare Intl - OAJ Jacksonville Albert J Ellis
ORDOAJ
Chicago O'Hare Intl
Sat 10/10
1:55 pm-10:22 pm
2 stops7h 27m
Jacksonville Albert J Ellis
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$408
ChicagoJacksonville
ORD Chicago O'Hare Intl - OAJ Jacksonville Albert J Ellis
ORDOAJ
Chicago O'Hare Intl
Mon 12/21
7:59 am-4:11 pm
1 stop7h 12m
Jacksonville Albert J Ellis
Mon 12/28
4:36 pm-11:00 pm
1 stop7h 24m
$477
ChicagoJacksonville
ORD Chicago O'Hare Intl - OAJ Jacksonville Albert J Ellis
ORDOAJ
Chicago O'Hare Intl
Sat 10/17
9:02 am-4:31 pm
1 stop6h 29m
Jacksonville Albert J Ellis
Tue 10/20
7:24 pm-12:08 am
1 stop5h 44m
$492
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Sat 10/17
1:27 pm-10:22 pm
2 stops7h 55m
Jacksonville Albert J Ellis
Tue 10/20
12:00 pm-4:14 pm
1 stop5h 14m
$502
ChicagoJacksonville
ORD Chicago O'Hare Intl - OAJ Jacksonville Albert J Ellis
ORDOAJ
Chicago O'Hare Intl
Sat 10/17
7:00 am-3:21 pm
2 stops7h 21m
Jacksonville Albert J Ellis
Tue 10/20
2:21 pm-8:38 pm
1 stop7h 17m
$502
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Wed 10/7
6:04 am-1:41 pm
1 stop6h 37m
Jacksonville Albert J Ellis
Sun 10/11
6:33 pm-10:33 pm
1 stop5h 00m
$557
ChicagoJacksonville
MDW Chicago Midway - OAJ Jacksonville Albert J Ellis
MDWOAJ
Chicago Midway
Thu 10/8
12:49 pm-5:53 pm
1 stop4h 04m
Jacksonville Albert J Ellis
Mon 10/12
6:00 am-12:47 pm
2 stops7h 47m
$733
Sorted by cheapest first
Compare providers for flights from Chicago to Jacksonville
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 Chicago to Jacksonville in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Jacksonville, North Carolina flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Jacksonville, North Carolina flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Jacksonville, North Carolina flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Jacksonville, North Carolina 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 Chicago-Jacksonville, North Carolina 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 Chicago to Jacksonville
Have a flexible travel schedule? Discover the best time to fly to Jacksonville from Chicago with our price prediction graph.
CHI-OAJ
ORD-OAJ
MDW-OAJ
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 Chicago to Jacksonville
CHI-OAJ
ORD-OAJ
MDW-OAJ
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 Chicago to Jacksonville. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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
Complete your trip
Flights by cabin class
Jacksonville flight routes
Other flight options
Other flights from Chicago
Popular flights
Top destinations
Alternative routes for Chicago to Jacksonville
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Jacksonville by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Jacksonville by cabin class
Find flights from Chicago to Jacksonville, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Jacksonville
Explore flights to Jacksonville departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 25, 2026.
Chicago and Jacksonville flights
Browse other Chicago and Jacksonville flight options. Last updated on September 25, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on September 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Jacksonville flights
Consider these flights traveling from Chicago to Jacksonville.
Top airline flying from Chicago to Jacksonville
Discover the top airline that operate flights from Chicago to Jacksonville. 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 September 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$138 | Average$422 | FlexibilityNo cancel fee | On-timeN/A |