$305+ 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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — CHI
Sep 3 — Sep 101
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 August 4, 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 August 4, 2026.
This Delta deal was found by Cheapflights users on 8/2. 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 9/112:10 pm
OAJ
- ORD
1 stop5h 41m
Delta
Mon 9/75:30 am
ORD
- OAJ
1 stop5h 00m
Delta
Deal found 8/2![Delta logo]()
$423
This Delta deal was found by Cheapflights users on 8/2. 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 9/112:10 pm
OAJ
- MDW
1 stop4h 34m
Delta
Mon 9/76:05 am
MDW
- OAJ
1 stop4h 25m
Delta
Deal found 8/2![Delta logo]()
$463
This American Airlines deal was found by Cheapflights users on 8/4. 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 9/17:09 pm
OAJ
- ORD
1 stop5h 43m
American Airlines
Mon 9/76:49 am
ORD
- OAJ
1 stop5h 36m
American Airlines
Deal found 8/4![American Airlines logo]()
$477
This American Airlines deal was found by Cheapflights users on 8/2. 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 8/85:15 pm
OAJ
- ORD
1 stop5h 42m
American Airlines
Wed 8/191:15 pm
ORD
- OAJ
1 stop4h 23m
American Airlines
Deal found 8/2![American Airlines logo]()
$485
This Delta deal was found by Cheapflights users on 7/31. 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 8/1512:10 pm
OAJ
- MDW
1 stop4h 28m
Delta
Wed 8/196:05 am
MDW
- OAJ
1 stop4h 25m
Delta
Deal found 7/31![Delta logo]()
$485
This Delta deal was found by Cheapflights users on 8/4. 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 8/84:15 pm
OAJ
- ORD
1 stop5h 40m
Delta
Wed 8/196:00 am
ORD
- OAJ
2 stops11h 07m
Delta
Deal found 8/4![Delta logo]()
$490
This Delta deal was found by Cheapflights users on 8/2. 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 8/52:27 pm
OAJ
- ORD
2 stops8h 57m
Delta
Wed 8/196:00 am
ORD
- OAJ
2 stops11h 07m
Delta
Deal found 8/2![Delta logo]()
$495
This Delta deal was found by Cheapflights users on 8/1. 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 8/1512:10 pm
OAJ
- ORD
1 stop5h 41m
Delta
Mon 8/175:30 am
ORD
- OAJ
1 stop5h 00m
Delta
Deal found 8/1![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 7/30. 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.
Fri 8/146:48 pm
OAJ
- ORD
1 stop6h 09m
Delta
Tue 8/1810:33 am
ORD
- OAJ
1 stop6h 34m
Delta
Deal found 7/30![Delta logo]()
$531
This Delta deal was found by Cheapflights users on 8/1. 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 8/1512:10 pm
OAJ
- MDW
1 stop4h 28m
Delta
Mon 8/176:05 am
MDW
- OAJ
1 stop4h 25m
Delta
Deal found 8/1![Delta logo]()
$537
This Delta deal was found by Cheapflights users on 8/2. 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 8/66:48 pm
OAJ
- ORD
1 stop6h 09m
Delta
Wed 8/196:40 am
ORD
- OAJ
1 stop6h 06m
Delta
Deal found 8/2![Delta logo]()
$540
This Delta deal was found by Cheapflights users on 7/30. 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.
Fri 8/76:48 pm
OAJ
- MDW
1 stop4h 48m
Delta
Fri 8/146:05 am
MDW
- OAJ
1 stop6h 41m
Delta
Deal found 7/30![Delta logo]()
$586
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 August 4, 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 August 4, 2026.
This Delta deal was found by Cheapflights users on 8/2. 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 9/112:10 pm
OAJ
- ORD
1 stop5h 41m
Delta
Mon 9/75:30 am
ORD
- OAJ
1 stop5h 00m
Delta
Deal found 8/2![Delta logo]()
$423
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/155:15 pm
OAJ
- ORD
1 stop5h 42m
American Airlines
Wed 8/196:49 am
ORD
- OAJ
1 stop5h 36m
American Airlines
Deal found 7/31![American Airlines logo]()
$485
This Delta deal was found by Cheapflights users on 8/1. 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 9/24:15 pm
OAJ
- ORD
1 stop5h 40m
Delta
Mon 9/75:30 am
ORD
- OAJ
1 stop5h 00m
Delta
Deal found 8/1![Delta logo]()
$423
This Delta deal was found by Cheapflights users on 8/2. 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 9/112:10 pm
OAJ
- MDW
1 stop4h 34m
Delta
Mon 9/76:05 am
MDW
- OAJ
1 stop4h 25m
Delta
Deal found 8/2![Delta logo]()
$463
This American Airlines deal was found by Cheapflights users on 8/2. 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 9/56:01 pm
OAJ
- ORD
1 stop7h 10m
American Airlines
Fri 9/114:45 pm
ORD
- OAJ
1 stop4h 59m
American Airlines
Deal found 8/2![American Airlines logo]()
$579
This Delta deal was found by Cheapflights users on 7/31. 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 8/156:00 am
OAJ
- ORD
1 stop7h 40m
Delta
Wed 8/196:00 am
ORD
- OAJ
2 stops11h 07m
Delta
Deal found 7/31![Delta logo]()
$490
This Delta deal was found by Cheapflights users on 7/31. 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 8/154:15 pm
OAJ
- MDW
1 stop7h 21m
Delta
Wed 8/191:25 pm
MDW
- OAJ
2 stops8h 04m
Delta
Deal found 7/31![Delta logo]()
$490
This Delta deal was found by Cheapflights users on 8/1. 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 8/1512:10 pm
OAJ
- ORD
1 stop5h 41m
Delta
Mon 8/175:30 am
ORD
- OAJ
1 stop5h 00m
Delta
Deal found 8/1![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 7/30. 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.
Fri 8/146:48 pm
OAJ
- ORD
1 stop6h 09m
Delta
Tue 8/1810:33 am
ORD
- OAJ
1 stop6h 34m
Delta
Deal found 7/30![Delta logo]()
$531
This Delta deal was found by Cheapflights users on 8/1. 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 8/166:00 am
OAJ
- MDW
1 stop4h 59m
Delta
Thu 8/206:05 am
MDW
- OAJ
1 stop4h 25m
Delta
Deal found 8/1![Delta logo]()
$785
Last-minute flights from Jacksonville to ChicagoDiscover last-minute flight deals from Jacksonville to Chicago. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from Jacksonville to Chicago. Data last updated August 4, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/2. 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 8/52:27 pm
OAJ
- ORD
2 stops8h 57m
Delta
Wed 8/196:00 am
ORD
- OAJ
2 stops11h 07m
Delta
Deal found 8/2![Delta logo]()
$495
This Delta deal was found by Cheapflights users on 8/2. 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 8/66:48 pm
OAJ
- ORD
1 stop6h 09m
Delta
Wed 8/196:40 am
ORD
- OAJ
1 stop6h 06m
Delta
Deal found 8/2![Delta logo]()
$540
This Delta deal was found by Cheapflights users on 7/30. 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.
Fri 8/76:48 pm
OAJ
- MDW
1 stop4h 48m
Delta
Fri 8/146:05 am
MDW
- OAJ
1 stop6h 41m
Delta
Deal found 7/30![Delta logo]()
$586
This American Airlines deal was found by Cheapflights users on 8/2. 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 8/85:15 pm
OAJ
- ORD
1 stop5h 42m
American Airlines
Wed 8/191:15 pm
ORD
- OAJ
1 stop4h 23m
American Airlines
Deal found 8/2![American Airlines logo]()
$485
This Delta deal was found by Cheapflights users on 8/4. 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 8/84:15 pm
OAJ
- ORD
1 stop5h 40m
Delta
Wed 8/196:00 am
ORD
- OAJ
2 stops11h 07m
Delta
Deal found 8/4![Delta logo]()
$490
This Delta deal was found by Cheapflights users on 7/30. 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.
Fri 8/146:48 pm
OAJ
- ORD
1 stop6h 09m
Delta
Tue 8/1810:33 am
ORD
- OAJ
1 stop6h 34m
Delta
Deal found 7/30![Delta logo]()
$531
This Delta deal was found by Cheapflights users on 7/31. 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 8/1512:10 pm
OAJ
- MDW
1 stop4h 28m
Delta
Wed 8/196:05 am
MDW
- OAJ
1 stop4h 25m
Delta
Deal found 7/31![Delta logo]()
$485
This Delta deal was found by Cheapflights users on 8/1. 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 8/1512:10 pm
OAJ
- ORD
1 stop5h 41m
Delta
Mon 8/175:30 am
ORD
- OAJ
1 stop5h 00m
Delta
Deal found 8/1![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 8/1. 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 8/1512:10 pm
OAJ
- MDW
1 stop4h 28m
Delta
Mon 8/176:05 am
MDW
- OAJ
1 stop4h 25m
Delta
Deal found 8/1![Delta logo]()
$537
This Delta deal was found by Cheapflights users on 8/2. 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 9/112:10 pm
OAJ
- ORD
1 stop5h 41m
Delta
Mon 9/75:30 am
ORD
- OAJ
1 stop5h 00m
Delta
Deal found 8/2![Delta logo]()
$423
This Delta deal was found by Cheapflights users on 8/2. 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 9/112:10 pm
OAJ
- MDW
1 stop4h 34m
Delta
Mon 9/76:05 am
MDW
- OAJ
1 stop4h 25m
Delta
Deal found 8/2![Delta logo]()
$463
This American Airlines deal was found by Cheapflights users on 8/4. 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 9/17:09 pm
OAJ
- ORD
1 stop5h 43m
American Airlines
Mon 9/76:49 am
ORD
- OAJ
1 stop5h 36m
American Airlines
Deal found 8/4![American Airlines logo]()
$477
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 August 4, 2026.
Search for one-way flight options from Jacksonville to Chicago. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
This Delta deal was found by Cheapflights users on 7/30. 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.
Fri 8/146:48 pm
OAJ
- ORD
1 stop6h 09m
Delta
Deal found 7/30![Delta logo]()
$305
This Delta deal was found by Cheapflights users on 7/30. 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.
Fri 8/146:48 pm
OAJ
- MDW
1 stop4h 48m
Delta
Deal found 7/30![Delta logo]()
$305
This Delta deal was found by Cheapflights users on 8/2. 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 9/84:15 pm
OAJ
- ORD
1 stop5h 41m
Delta
Deal found 8/2![Delta logo]()
$333
This American Airlines deal was found by Cheapflights users on 7/31. 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 9/15:15 pm
OAJ
- ORD
1 stop7h 37m
American Airlines
Deal found 7/31![American Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 7/31. 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 9/112:10 pm
OAJ
- MDW
1 stop4h 34m
Delta
Deal found 7/31![Delta logo]()
$343
This Delta deal was found by Cheapflights users on 7/31. 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 9/16:00 am
OAJ
- ORD
2 stops8h 08m
Delta
Deal found 7/31![Delta logo]()
$348
This American Airlines deal was found by Cheapflights users on 8/2. 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 8/115:15 pm
OAJ
- ORD
1 stop7h 37m
American Airlines
Deal found 8/2![American Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 8/2. 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 8/1112:10 pm
OAJ
- ORD
2 stops9h 20m
Delta
Deal found 8/2![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 8/2. 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 8/96:00 am
OAJ
- ORD
1 stop7h 40m
Delta
Deal found 8/2![Delta logo]()
$445
This American Airlines deal was found by Cheapflights users on 8/2. 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.
Sun 8/93:06 pm
OAJ
- ORD
2 stops9h 31m
American Airlines
Deal found 8/2![American Airlines logo]()
$450
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 August 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $423 (Delta) |
One-way from | $305 (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 2,558,603 searches. Data last updated August 4, 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 - ORD
OAJORD
Jacksonville Albert J Ellis
Tue 9/1
12:10 pm-4:51 pm
1 stop5h 41m
Chicago O'Hare Intl
Mon 9/7
5:30 am-11:30 am
1 stop5h 00m
$423
JacksonvilleChicago
OAJ - ORD
OAJORD
Jacksonville Albert J Ellis
Wed 9/2
4:15 pm-8:55 pm
1 stop5h 40m
Chicago O'Hare Intl
Mon 9/7
5:30 am-11:30 am
1 stop5h 00m
$423
Quickest round-trip
JacksonvilleChicago
OAJ - MDW
OAJMDW
Jacksonville Albert J Ellis
Tue 9/1
12:10 pm-3:44 pm
1 stop4h 34m
Chicago Midway
Mon 9/7
6:05 am-11:30 am
1 stop4h 25m
$463
JacksonvilleChicago
OAJ - ORD
OAJORD
Jacksonville Albert J Ellis
Sat 8/15
5:15 pm-9:57 pm
1 stop5h 42m
Chicago O'Hare Intl
Wed 8/19
6:49 am-1:25 pm
1 stop5h 36m
$485
JacksonvilleChicago
OAJ - ORD
OAJORD
Jacksonville Albert J Ellis
Sat 8/15
6:00 am-12:40 pm
1 stop7h 40m
Chicago O'Hare Intl
Wed 8/19
6:00 am-6:07 pm
2 stops11h 07m
$490
JacksonvilleChicago
OAJ - MDW
OAJMDW
Jacksonville Albert J Ellis
Sat 8/15
4:15 pm-10:36 pm
1 stop7h 21m
Chicago Midway
Wed 8/19
1:25 pm-10:29 pm
2 stops8h 04m
$490
JacksonvilleChicago
OAJ - ORD
OAJORD
Jacksonville Albert J Ellis
Sat 8/15
12:10 pm-4:51 pm
1 stop5h 41m
Chicago O'Hare Intl
Mon 8/17
5:30 am-11:30 am
1 stop5h 00m
$511
JacksonvilleChicago
OAJ - ORD
OAJORD
Jacksonville Albert J Ellis
Fri 8/14
6:48 pm-11:57 pm
1 stop6h 09m
Chicago O'Hare Intl
Tue 8/18
10:33 am-6:07 pm
1 stop6h 34m
$531
JacksonvilleChicago
OAJ - ORD
OAJORD
Jacksonville Albert J Ellis
Sat 9/5
6:01 pm-12:11 am
1 stop7h 10m
Chicago O'Hare Intl
Fri 9/11
4:45 pm-10:44 pm
1 stop4h 59m
$579
JacksonvilleChicago
OAJ - MDW
OAJMDW
Jacksonville Albert J Ellis
Sun 8/16
6:00 am-9:59 am
1 stop4h 59m
Chicago Midway
Thu 8/20
6:05 am-11:30 am
1 stop4h 25m
$785
Showing 1-10 of 20 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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | 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
OAJ-MDW
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
OAJ-MDW
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
Lansing
Merrillville
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 August 4, 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 August 4, 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 August 4, 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 2,558,603 searches. Data last updated August 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$397 | Average$532 | FlexibilityNo cancel fee | On-time71% |