$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 7/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OAJ
Jun 4 — Jun 111
Round-trip
1 adult, Economy
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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
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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 May 5, 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 May 5, 2026.
This Delta deal was found by Cheapflights users on 5/4. 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 7/46:00 am
MDW
- OAJ
1 stop4h 31m
Delta
Wed 7/86:44 pm
OAJ
- MDW
1 stop4h 31m
Delta
Deal found 5/4![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 5/4. 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 7/45:30 am
ORD
- OAJ
1 stop5h 01m
Delta
Wed 7/84:35 pm
OAJ
- ORD
1 stop6h 33m
Delta
Deal found 5/4![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 5/4. 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.
Mon 6/15:30 am
ORD
- OAJ
1 stop4h 35m
Delta
Mon 6/154:45 pm
OAJ
- ORD
1 stop4h 47m
Delta
Deal found 5/4![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 5/3. 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 6/306:00 am
MDW
- OAJ
1 stop4h 21m
Delta
Tue 7/76:00 am
OAJ
- MDW
1 stop5h 05m
Delta
Deal found 5/3![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 5/3. 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 6/305:30 am
ORD
- OAJ
1 stop4h 51m
Delta
Tue 7/76:44 pm
OAJ
- ORD
1 stop6h 09m
Delta
Deal found 5/3![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 4/30. 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 6/195:30 am
ORD
- OAJ
1 stop4h 51m
Delta
Sun 6/2112:06 pm
OAJ
- ORD
1 stop5h 58m
Delta
Deal found 4/30![Delta logo]()
$417
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Sat 5/305:00 am
ORD
- OAJ
1 stop6h 49m
American Airlines
Sat 6/66:11 pm
OAJ
- ORD
1 stop6h 47m
American Airlines
Deal found 5/4![American Airlines logo]()
$432
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Mon 6/296:29 am
ORD
- OAJ
1 stop7h 06m
American Airlines
Mon 7/131:14 pm
OAJ
- ORD
1 stop5h 25m
American Airlines
Deal found 5/4![American Airlines logo]()
$446
This American Airlines deal was found by Cheapflights users on 5/2. 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 8/16:30 am
ORD
- OAJ
1 stop7h 02m
American Airlines
Sat 8/86:01 pm
OAJ
- ORD
1 stop6h 58m
American Airlines
Deal found 5/2![American Airlines logo]()
$453
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:39 am
ORD
- OAJ
1 stop6h 10m
American Airlines
Thu 5/213:07 pm
OAJ
- ORD
1 stop7h 30m
American Airlines
Deal found 4/30![American Airlines logo]()
$497
This American Airlines deal was found by Cheapflights users on 5/5. 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 5/205:00 am
ORD
- OAJ
1 stop4h 26m
American Airlines
Sun 5/241:14 pm
OAJ
- ORD
1 stop4h 29m
American Airlines
Deal found 5/5![American Airlines logo]()
$501
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Sat 7/48:29 am
ORD
- OAJ
2 stops8h 16m
American Airlines
Wed 7/86:11 pm
OAJ
- ORD
1 stop6h 50m
American Airlines
Deal found 5/4![American Airlines logo]()
$518
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 May 5, 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 May 5, 2026.
This Delta deal was found by Cheapflights users on 5/4. 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.
Mon 6/15:30 am
ORD
- OAJ
1 stop4h 35m
Delta
Mon 6/154:45 pm
OAJ
- ORD
1 stop4h 47m
Delta
Deal found 5/4![Delta logo]()
$381
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:39 am
ORD
- OAJ
1 stop6h 10m
American Airlines
Thu 5/213:07 pm
OAJ
- ORD
1 stop7h 30m
American Airlines
Deal found 4/30![American Airlines logo]()
$497
This Delta deal was found by Cheapflights users on 5/3. 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 6/306:00 am
MDW
- OAJ
1 stop4h 21m
Delta
Tue 7/76:00 am
OAJ
- MDW
1 stop5h 05m
Delta
Deal found 5/3![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 5/1. 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.
Fri 6/195:30 am
ORD
- OAJ
1 stop4h 51m
Delta
Sun 6/2112:06 pm
OAJ
- ORD
1 stop5h 58m
Delta
Deal found 5/1![Delta logo]()
$417
This American Airlines deal was found by Cheapflights users on 5/2. 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 8/16:35 am
ORD
- OAJ
2 stops6h 57m
American Airlines
Sat 8/88:04 pm
OAJ
- ORD
1 stop4h 55m
American Airlines
Deal found 5/2![American Airlines logo]()
$564
This Delta deal was found by Cheapflights users on 5/5. 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 5/2012:53 pm
MDW
- OAJ
1 stop4h 12m
Delta
Sun 5/244:07 pm
OAJ
- MDW
1 stop6h 02m
Delta
Deal found 5/5![Delta logo]()
$527
This American Airlines deal was found by Cheapflights users on 5/2. 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 5/95:00 am
ORD
- OAJ
2 stops9h 49m
American Airlines
Mon 5/114:17 pm
OAJ
- ORD
2 stops8h 21m
American Airlines
Deal found 5/2![American Airlines logo]()
$580
This Delta deal was found by Cheapflights users on 5/2. 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.
Fri 5/85:30 am
ORD
- OAJ
1 stop4h 36m
Delta
Sun 5/107:32 pm
OAJ
- ORD
1 stop5h 27m
Delta
Deal found 5/2![Delta logo]()
$585
This American Airlines deal was found by Cheapflights users on 5/2. 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.
Mon 6/294:12 pm
ORD
- OAJ
2 stops6h 44m
American Airlines
Mon 7/131:14 pm
OAJ
- ORD
1 stop5h 24m
American Airlines
Deal found 5/2![American Airlines logo]()
$775
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 5/2012:53 pm
MDW
- OAJ
1 stop4h 12m
Delta
Thu 5/214:07 pm
OAJ
- MDW
1 stop6h 02m
Delta
Deal found 4/30![Delta logo]()
$653
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Sat 5/304:30 pm
ORD
- OAJ
2 stops6h 26m
American Airlines
Sat 6/61:14 pm
OAJ
- ORD
1 stop4h 29m
American Airlines
Deal found 5/4![American Airlines logo]()
$776
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/194:12 pm
ORD
- OAJ
2 stops6h 44m
American Airlines
Sun 6/211:14 pm
OAJ
- ORD
1 stop5h 28m
American Airlines
Deal found 4/30![American Airlines logo]()
$810
This Delta deal was found by Cheapflights users on 5/4. 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 7/46:00 am
MDW
- OAJ
1 stop4h 31m
Delta
Wed 7/86:00 am
OAJ
- MDW
2 stops7h 38m
Delta
Deal found 5/4![Delta logo]()
$997
This Delta deal was found by Cheapflights users on 5/4. 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 5/301:22 pm
MDW
- OAJ
2 stops7h 43m
Delta
Sat 6/64:07 pm
OAJ
- MDW
1 stop6h 02m
Delta
Deal found 5/4![Delta logo]()
$1,067
Last-minute flights from Chicago to JacksonvilleDiscover last-minute flight deals from Chicago to Jacksonville. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Jacksonville. Data last updated May 5, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/2. 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.
Sat 5/99:10 am
ORD
- OAJ
1 stop5h 17m
Delta
Sun 5/107:32 pm
OAJ
- ORD
1 stop5h 27m
Delta
Deal found 5/2![Delta logo]()
$530
This American Airlines deal was found by Cheapflights users on 5/2. 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 5/91:54 pm
ORD
- OAJ
1 stop4h 30m
American Airlines
Mon 5/117:55 pm
OAJ
- ORD
1 stop4h 59m
American Airlines
Deal found 5/2![American Airlines logo]()
$570
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:39 am
ORD
- OAJ
1 stop6h 10m
American Airlines
Thu 5/213:07 pm
OAJ
- ORD
1 stop7h 30m
American Airlines
Deal found 4/30![American Airlines logo]()
$497
This American Airlines deal was found by Cheapflights users on 5/5. 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 5/205:00 am
ORD
- OAJ
1 stop4h 26m
American Airlines
Sun 5/241:14 pm
OAJ
- ORD
1 stop4h 29m
American Airlines
Deal found 5/5![American Airlines logo]()
$501
This Delta deal was found by Cheapflights users on 5/5. 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 5/2012:53 pm
MDW
- OAJ
1 stop4h 12m
Delta
Sun 5/244:07 pm
OAJ
- MDW
1 stop6h 02m
Delta
Deal found 5/5![Delta logo]()
$527
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Sat 5/305:00 am
ORD
- OAJ
1 stop6h 49m
American Airlines
Sat 6/66:11 pm
OAJ
- ORD
1 stop6h 47m
American Airlines
Deal found 5/4![American Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 5/4. 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.
Mon 6/15:30 am
ORD
- OAJ
1 stop4h 35m
Delta
Mon 6/154:45 pm
OAJ
- ORD
1 stop4h 47m
Delta
Deal found 5/4![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 4/30. 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 6/195:30 am
ORD
- OAJ
1 stop4h 51m
Delta
Sun 6/2112:06 pm
OAJ
- ORD
1 stop5h 58m
Delta
Deal found 4/30![Delta logo]()
$417
This American Airlines deal was found by Cheapflights users on 5/3. 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 6/245:10 am
ORD
- OAJ
1 stop6h 39m
American Airlines
Sun 6/286:41 am
OAJ
- ORD
1 stop6h 39m
American Airlines
Deal found 5/3![American Airlines logo]()
$562
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Mon 6/296:29 am
ORD
- OAJ
1 stop7h 06m
American Airlines
Mon 7/131:14 pm
OAJ
- ORD
1 stop5h 25m
American Airlines
Deal found 5/4![American Airlines logo]()
$446
This Delta deal was found by Cheapflights users on 5/3. 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 6/306:00 am
MDW
- OAJ
1 stop4h 21m
Delta
Tue 7/76:00 am
OAJ
- MDW
1 stop5h 05m
Delta
Deal found 5/3![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 5/3. 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 6/305:30 am
ORD
- OAJ
1 stop4h 51m
Delta
Tue 7/76:44 pm
OAJ
- ORD
1 stop6h 09m
Delta
Deal found 5/3![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 May 5, 2026.
Search for one-way flight options from Chicago to Jacksonville. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
This Delta deal was found by Cheapflights users on 5/3. 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 29m
Delta
Deal found 5/3![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 5/3. 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 7/183:35 pm
ORD
- OAJ
1 stop5h 54m
Delta
Deal found 5/3![Delta logo]()
$209
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/205:00 am
ORD
- OAJ
1 stop4h 26m
American Airlines
Deal found 4/30![American Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 5/2. 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.
Sat 8/19:00 am
ORD
- OAJ
1 stop5h 54m
Delta
Deal found 5/2![Delta logo]()
$328
This American Airlines deal was found by Cheapflights users on 5/3. 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 7/186:35 am
ORD
- OAJ
2 stops6h 57m
American Airlines
Deal found 5/3![American Airlines logo]()
$363
This American Airlines deal was found by Cheapflights users on 5/2. 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 8/16:35 am
ORD
- OAJ
2 stops6h 57m
American Airlines
Deal found 5/2![American Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 5/3. 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 5/159:49 am
ORD
- OAJ
1 stop7h 16m
Delta
Deal found 5/3![Delta logo]()
$440
This American Airlines deal was found by Cheapflights users on 5/3. 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 5/154:55 pm
ORD
- OAJ
2 stops6h 02m
American Airlines
Deal found 5/3![American Airlines logo]()
$682
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 May 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $379 (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 May 5, 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
ORD - OAJ
ORDOAJ
Chicago O'Hare Intl
Mon 6/1
5:30 am-11:05 am
1 stop4h 35m
Jacksonville Albert J Ellis
Mon 6/15
4:45 pm-8:32 pm
1 stop4h 47m
$381
ChicagoJacksonville
MDW - OAJ
MDWOAJ
Chicago Midway
Tue 6/30
6:00 am-11:21 am
1 stop4h 21m
Jacksonville Albert J Ellis
Tue 7/7
6:00 am-10:05 am
1 stop5h 05m
$398
ChicagoJacksonville
ORD - OAJ
ORDOAJ
Chicago O'Hare Intl
Fri 6/19
5:30 am-11:21 am
1 stop4h 51m
Jacksonville Albert J Ellis
Sun 6/21
12:06 pm-5:04 pm
1 stop5h 58m
$417
ChicagoJacksonville
ORD - OAJ
ORDOAJ
Chicago O'Hare Intl
Wed 5/20
8:39 am-3:49 pm
1 stop6h 10m
Jacksonville Albert J Ellis
Thu 5/21
3:07 pm-9:37 pm
1 stop7h 30m
$497
ChicagoJacksonville
MDW - OAJ
MDWOAJ
Chicago Midway
Wed 5/20
12:53 pm-6:05 pm
1 stop4h 12m
Jacksonville Albert J Ellis
Sun 5/24
4:07 pm-9:09 pm
1 stop6h 02m
$527
ChicagoJacksonville
ORD - OAJ
ORDOAJ
Chicago O'Hare Intl
Sat 8/1
6:35 am-2:32 pm
2 stops6h 57m
Jacksonville Albert J Ellis
Sat 8/8
8:04 pm-11:59 pm
1 stop4h 55m
$564
ChicagoJacksonville
ORD - OAJ
ORDOAJ
Chicago O'Hare Intl
Sat 5/9
5:00 am-3:49 pm
2 stops9h 49m
Jacksonville Albert J Ellis
Mon 5/11
4:17 pm-11:38 pm
2 stops8h 21m
$580
ChicagoJacksonville
ORD - OAJ
ORDOAJ
Chicago O'Hare Intl
Fri 5/8
5:30 am-11:06 am
1 stop4h 36m
Jacksonville Albert J Ellis
Sun 5/10
7:32 pm-11:59 pm
1 stop5h 27m
$585
ChicagoJacksonville
MDW - OAJ
MDWOAJ
Chicago Midway
Wed 5/20
12:53 pm-6:05 pm
1 stop4h 12m
Jacksonville Albert J Ellis
Thu 5/21
4:07 pm-9:09 pm
1 stop6h 02m
$653
ChicagoJacksonville
ORD - OAJ
ORDOAJ
Chicago O'Hare Intl
Mon 6/29
4:12 pm-11:56 pm
2 stops6h 44m
Jacksonville Albert J Ellis
Mon 7/13
1:14 pm-5:38 pm
1 stop5h 24m
$775
Showing 1-10 of 22 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 May.
| 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.
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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 May 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$256 | Average$434 | FlexibilityNo cancel fee | On-time71% |