$209+ Cheap flights from Chicago (CHI) to Jacksonville, NC (OAJ)
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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAJ
Jul 11 — Jul 181
Round-trip
1 adult, Economy
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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
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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 June 11, 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 June 11, 2026.
This Delta deal was found by Cheapflights users on 6/7. 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 7/46:00 am
MDW
- OAJ
1 stop4h 31m
Delta
Wed 7/86:44 pm
OAJ
- MDW
1 stop4h 31m
Delta
Deal found 6/7![Delta logo]()
$367
This Delta deal was found by Cheapflights users on 6/7. 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 7/45:30 am
ORD
- OAJ
1 stop5h 01m
Delta
Sat 7/1112:11 pm
OAJ
- ORD
1 stop7h 35m
Delta
Deal found 6/7![Delta logo]()
$367
This Delta deal was found by Cheapflights users on 6/7. 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 7/47:01 am
ORD
- OAJ
2 stops7h 58m
Delta
Tue 7/74:43 pm
OAJ
- ORD
1 stop4h 50m
Delta
Deal found 6/7![Delta logo]()
$372
This Delta deal was found by Cheapflights users on 6/7. 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 7/1412:41 pm
MDW
- OAJ
1 stop4h 21m
Delta
Tue 7/216:44 pm
OAJ
- MDW
1 stop4h 31m
Delta
Deal found 6/7![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 6/7. 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 8/115:30 am
ORD
- OAJ
1 stop5h 00m
Delta
Tue 8/182:27 pm
OAJ
- ORD
1 stop5h 22m
Delta
Deal found 6/7![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 6/7. 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 7/76:00 am
ORD
- OAJ
2 stops11h 02m
Delta
Sat 7/1112:11 pm
OAJ
- ORD
1 stop6h 01m
Delta
Deal found 6/7![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 6/7. 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 7/44:25 pm
MDW
- OAJ
1 stop5h 05m
Delta
Fri 7/104:43 pm
OAJ
- MDW
1 stop6h 32m
Delta
Deal found 6/7![Delta logo]()
$386
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:45 pm
ORD
- OAJ
1 stop4h 31m
American Airlines
Tue 7/76:11 pm
OAJ
- ORD
1 stop4h 49m
American Airlines
Deal found 6/10![American Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 6/7. 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 7/1611:05 am
MDW
- OAJ
1 stop5h 57m
Delta
Sat 7/184:35 pm
OAJ
- MDW
1 stop6h 40m
Delta
Deal found 6/7![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 6/7. 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 8/113:25 pm
ORD
- OAJ
1 stop6h 04m
Delta
Mon 8/176:00 am
OAJ
- ORD
1 stop5h 13m
Delta
Deal found 6/7![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 6/7. 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 7/87:00 am
ORD
- OAJ
2 stops10h 02m
Delta
Sat 7/1112:11 pm
OAJ
- ORD
1 stop6h 01m
Delta
Deal found 6/7![Delta logo]()
$403
This Delta deal was found by Cheapflights users on 6/7. 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 7/41:26 pm
MDW
- OAJ
2 stops8h 04m
Delta
Tue 7/76:44 pm
OAJ
- MDW
1 stop4h 31m
Delta
Deal found 6/7![Delta logo]()
$404
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 June 11, 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 June 11, 2026.
This Delta deal was found by Cheapflights users on 6/7. 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 7/148:03 am
ORD
- OAJ
1 stop6h 51m
Delta
Tue 7/214:43 pm
OAJ
- ORD
1 stop4h 50m
Delta
Deal found 6/7![Delta logo]()
$379
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:45 pm
ORD
- OAJ
1 stop4h 31m
American Airlines
Tue 7/76:11 pm
OAJ
- ORD
1 stop4h 49m
American Airlines
Deal found 6/10![American Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 6/7. 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 8/115:30 am
ORD
- OAJ
1 stop5h 00m
Delta
Sun 8/162:27 pm
OAJ
- ORD
1 stop7h 28m
Delta
Deal found 6/7![Delta logo]()
$398
This American Airlines deal was found by Cheapflights users on 6/8. 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 8/46:30 am
ORD
- OAJ
1 stop7h 02m
American Airlines
Fri 8/71:54 pm
OAJ
- ORD
1 stop4h 48m
American Airlines
Deal found 6/8![American Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 6/7. 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 7/155:30 am
ORD
- OAJ
1 stop4h 49m
Delta
Sat 7/184:35 pm
OAJ
- ORD
1 stop4h 58m
Delta
Deal found 6/7![Delta logo]()
$398
This American Airlines deal was found by Cheapflights users on 6/6. 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 7/106:30 am
ORD
- OAJ
1 stop7h 02m
American Airlines
Sun 7/123:07 pm
OAJ
- ORD
1 stop7h 53m
American Airlines
Deal found 6/6![American Airlines logo]()
$451
This Delta deal was found by Cheapflights users on 6/7. 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 7/1711:05 am
MDW
- OAJ
1 stop5h 57m
Delta
Mon 7/206:44 pm
OAJ
- MDW
1 stop4h 31m
Delta
Deal found 6/7![Delta logo]()
$417
This American Airlines deal was found by Cheapflights users on 6/6. 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 6/296:29 am
ORD
- OAJ
1 stop5h 20m
American Airlines
Mon 7/131:14 pm
OAJ
- ORD
1 stop5h 25m
American Airlines
Deal found 6/6![American Airlines logo]()
$452
This Delta deal was found by Cheapflights users on 6/6. 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 9/175:30 am
ORD
- OAJ
1 stop7h 11m
Delta
Sun 9/206:00 am
OAJ
- ORD
1 stop5h 09m
Delta
Deal found 6/6![Delta logo]()
$417
This Delta deal was found by Cheapflights users on 6/7. 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 7/186:00 am
MDW
- OAJ
1 stop4h 18m
Delta
Tue 7/216:44 pm
OAJ
- MDW
1 stop4h 31m
Delta
Deal found 6/7![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 6/7. 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 8/126:05 am
MDW
- OAJ
1 stop4h 25m
Delta
Sat 8/1512:10 pm
OAJ
- MDW
1 stop4h 28m
Delta
Deal found 6/7![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 6/7. 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 7/186:00 am
MDW
- OAJ
1 stop4h 18m
Delta
Wed 7/226:00 am
OAJ
- MDW
2 stops7h 38m
Delta
Deal found 6/7![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 6/7. 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 7/47:01 am
ORD
- OAJ
2 stops7h 58m
Delta
Wed 7/84:43 pm
OAJ
- ORD
1 stop8h 10m
Delta
Deal found 6/7![Delta logo]()
$447
This Delta deal was found by Cheapflights users on 6/7. 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 7/155:30 am
ORD
- OAJ
1 stop4h 49m
Delta
Thu 7/166:44 pm
OAJ
- ORD
1 stop6h 09m
Delta
Deal found 6/7![Delta logo]()
$448
This Delta deal was found by Cheapflights users on 6/7. 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 7/165:30 am
ORD
- OAJ
1 stop4h 49m
Delta
Thu 7/166:44 pm
OAJ
- ORD
1 stop6h 09m
Delta
Deal found 6/7![Delta logo]()
$458
This Delta deal was found by Cheapflights users on 6/7. 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 7/26:00 am
MDW
- OAJ
1 stop4h 21m
Delta
Fri 7/104:43 pm
OAJ
- MDW
1 stop6h 32m
Delta
Deal found 6/7![Delta logo]()
$460
This Delta deal was found by Cheapflights users on 6/9. 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 9/39:54 am
ORD
- OAJ
1 stop4h 26m
Delta
Mon 9/76:00 am
OAJ
- ORD
2 stops8h 08m
Delta
Deal found 6/9![Delta logo]()
$463
This Delta deal was found by Cheapflights users on 6/7. 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 7/1712:41 pm
MDW
- OAJ
1 stop4h 21m
Delta
Sun 7/196:44 pm
OAJ
- MDW
1 stop4h 31m
Delta
Deal found 6/7![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 6/9. 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 9/36:05 am
MDW
- OAJ
1 stop4h 25m
Delta
Mon 9/76:00 am
OAJ
- MDW
2 stops7h 39m
Delta
Deal found 6/9![Delta logo]()
$537
This Delta deal was found by Cheapflights users on 6/6. 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 7/1011:05 am
MDW
- OAJ
1 stop5h 57m
Delta
Sun 7/126:44 pm
OAJ
- MDW
1 stop4h 31m
Delta
Deal found 6/6![Delta logo]()
$538
Last-minute flights from Chicago to JacksonvilleDiscover last-minute flight deals from Chicago to Jacksonville. Data last updated June 11, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Jacksonville. Data last updated June 11, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:45 pm
ORD
- OAJ
1 stop4h 31m
American Airlines
Tue 7/76:11 pm
OAJ
- ORD
1 stop4h 49m
American Airlines
Deal found 6/10![American Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 6/7. 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 7/46:00 am
MDW
- OAJ
1 stop4h 31m
Delta
Tue 7/76:44 pm
OAJ
- MDW
1 stop4h 31m
Delta
Deal found 6/7![Delta logo]()
$367
This Delta deal was found by Cheapflights users on 6/7. 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 7/45:30 am
ORD
- OAJ
1 stop5h 01m
Delta
Sat 7/1112:11 pm
OAJ
- ORD
1 stop7h 35m
Delta
Deal found 6/7![Delta logo]()
$367
This Delta deal was found by Cheapflights users on 6/7. 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 7/44:25 pm
MDW
- OAJ
1 stop5h 05m
Delta
Fri 7/104:43 pm
OAJ
- MDW
1 stop6h 32m
Delta
Deal found 6/7![Delta logo]()
$386
This Delta deal was found by Cheapflights users on 6/7. 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 7/76:00 am
ORD
- OAJ
2 stops11h 02m
Delta
Sat 7/1112:11 pm
OAJ
- ORD
1 stop6h 01m
Delta
Deal found 6/7![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 6/7. 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 7/76:00 am
MDW
- OAJ
1 stop4h 19m
Delta
Wed 7/86:44 pm
OAJ
- MDW
1 stop4h 31m
Delta
Deal found 6/7![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 6/7. 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 7/75:30 am
ORD
- OAJ
1 stop4h 49m
Delta
Tue 7/74:43 pm
OAJ
- ORD
1 stop4h 50m
Delta
Deal found 6/7![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 6/7. 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 7/76:00 am
MDW
- OAJ
1 stop4h 19m
Delta
Fri 7/106:44 pm
OAJ
- MDW
1 stop4h 31m
Delta
Deal found 6/7![Delta logo]()
$417
This Delta deal was found by Cheapflights users on 6/7. 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 7/89:45 am
ORD
- OAJ
1 stop7h 17m
Delta
Sat 7/1112:11 pm
OAJ
- ORD
1 stop7h 35m
Delta
Deal found 6/7![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 6/7. 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 7/1412:41 pm
MDW
- OAJ
1 stop4h 21m
Delta
Sat 7/184:35 pm
OAJ
- MDW
1 stop6h 40m
Delta
Deal found 6/7![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 6/7. 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 7/148:03 am
ORD
- OAJ
1 stop6h 51m
Delta
Mon 7/2012:05 pm
OAJ
- ORD
1 stop6h 07m
Delta
Deal found 6/7![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 6/7. 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 7/1611:05 am
MDW
- OAJ
1 stop5h 57m
Delta
Tue 7/216:44 pm
OAJ
- MDW
1 stop4h 31m
Delta
Deal found 6/7![Delta logo]()
$398
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 June 11, 2026.
Search for one-way flight options from Chicago to Jacksonville. Find affordable one-way fares based on user searches. Data last updated June 11, 2026.
This Delta deal was found by Cheapflights users on 6/6. 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 9/176:40 am
ORD
- OAJ
1 stop6h 01m
Delta
Deal found 6/6![Delta logo]()
$209
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 June 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $367 (Delta) |
One-way from | $209 (Delta) |
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 2,558,603 searches. Data last updated June 11, 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
ChicagoJacksonville
ORD - OAJ
ORDOAJ
Chicago O'Hare Intl
Tue 7/14
8:03 am-3:54 pm
1 stop6h 51m
Jacksonville Albert J Ellis
Tue 7/21
4:43 pm-8:33 pm
1 stop4h 50m
$379
ChicagoJacksonville
ORD - OAJ
ORDOAJ
Chicago O'Hare Intl
Fri 7/3
4:45 pm-10:16 pm
1 stop4h 31m
Jacksonville Albert J Ellis
Tue 7/7
6:11 pm-10:00 pm
1 stop4h 49m
$393
ChicagoJacksonville
ORD - OAJ
ORDOAJ
Chicago O'Hare Intl
Tue 8/11
5:30 am-11:30 am
1 stop5h 00m
Jacksonville Albert J Ellis
Sun 8/16
2:27 pm-8:55 pm
1 stop7h 28m
$398
ChicagoJacksonville
ORD - OAJ
ORDOAJ
Chicago O'Hare Intl
Wed 7/15
5:30 am-11:19 am
1 stop4h 49m
Jacksonville Albert J Ellis
Sat 7/18
4:35 pm-8:33 pm
1 stop4h 58m
$398
ChicagoJacksonville
ORD - OAJ
ORDOAJ
Chicago O'Hare Intl
Tue 8/4
6:30 am-2:32 pm
1 stop7h 02m
Jacksonville Albert J Ellis
Fri 8/7
1:54 pm-5:42 pm
1 stop4h 48m
$417
ChicagoJacksonville
MDW - OAJ
MDWOAJ
Chicago Midway
Fri 7/17
11:05 am-6:02 pm
1 stop5h 57m
Jacksonville Albert J Ellis
Mon 7/20
6:44 pm-10:15 pm
1 stop4h 31m
$417
ChicagoJacksonville
ORD - OAJ
ORDOAJ
Chicago O'Hare Intl
Thu 9/17
5:30 am-1:41 pm
1 stop7h 11m
Jacksonville Albert J Ellis
Sun 9/20
6:00 am-10:09 am
1 stop5h 09m
$417
Quickest round-trip
ChicagoJacksonville
MDW - OAJ
MDWOAJ
Chicago Midway
Sat 7/18
6:00 am-11:18 am
1 stop4h 18m
Jacksonville Albert J Ellis
Tue 7/21
6:44 pm-10:15 pm
1 stop4h 31m
$439
ChicagoJacksonville
MDW - OAJ
MDWOAJ
Chicago Midway
Wed 8/12
6:05 am-11:30 am
1 stop4h 25m
Jacksonville Albert J Ellis
Sat 8/15
12:10 pm-3:38 pm
1 stop4h 28m
$439
ChicagoJacksonville
MDW - OAJ
MDWOAJ
Chicago Midway
Sat 7/18
6:00 am-11:18 am
1 stop4h 18m
Jacksonville Albert J Ellis
Wed 7/22
6:00 am-12:38 pm
2 stops7h 38m
$444
Showing 1-10 of 21 resultsSorted 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 June.
| 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
MDW-OAJ
ORD-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
MDW-OAJ
ORD-OAJ
No data available for this route at this time. Please check back soon.
Related info for your journey
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Other flights to Jacksonville
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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 2,558,603 searches. Data last updated June 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$256 | Average$479 | FlexibilityNo cancel fee | On-time71% |