$134+ Cheap flights from Chicago (CHI) to Jacksonville (JAX)
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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAX
Dec 4 — Dec 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
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.Cheapflights Tip: The best prices from Chicago to Jacksonville are usually found in January or June, booked 81 days in advance, depart on a Saturday or Wednesday and return on a Thursday
Cheap flight deals from Chicago to Jacksonville
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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 November 4, 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 November 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1010:29 pm -
1 stop17h 33m
Sun 12/133:05 pm -
2 stops17h 15m
Deal found 10/31![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:19 am -
1 stop8h 04m
Tue 12/13:20 pm -
2 stops25h 50m
Deal found 11/1![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:55 am -
1 stop23h 50m
Sun 11/157:03 pm -
2 stops21h 34m
Deal found 11/1![Multiple Airlines logo]()
$308
This Trip.com deal was found by Cheapflights users on 10/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:08 am -
1 stop11h 03m
Sun 11/157:03 pm -
1 stop5h 44m
Deal found 10/31![Frontier logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:49 am -
1 stop8h 18m
Mon 11/303:56 pm -
2 stops54h 39m
Deal found 11/2![Multiple Airlines logo]()
$311
This Trip.com deal was found by Cheapflights users on 10/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:08 am -
1 stop11h 03m
Sat 11/147:16 pm -
1 stop5h 31m
Deal found 10/31![Frontier logo]()
$312
This Cheapflightsfares deal was found by Cheapflights users on 10/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:49 am -
1 stop8h 18m
Mon 11/305:59 pm -
1 stop6h 19m
Deal found 10/31![Frontier logo]()
$313
This Expedia deal was found by Cheapflights users on 11/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:00 am -
1 stop11h 57m
Sun 11/225:59 pm -
1 stop6h 19m
Deal found 11/3![Multiple Airlines logo]()
$317
This Frontier deal was found by Cheapflights users on 11/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/231:11 pm -
1 stop5h 40m
Fri 1/18:36 pm -
1 stop4h 25m
Deal found 11/1![Frontier logo]()
$318
This CheapOair deal was found by Cheapflights users on 11/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:00 am -
1 stop11h 57m
Fri 11/205:59 pm -
1 stop6h 19m
Deal found 11/3![Multiple Airlines logo]()
$318
This Frontier deal was found by Cheapflights users on 11/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:49 am -
1 stop8h 18m
Fri 11/275:59 pm -
1 stop6h 19m
Deal found 11/1![Frontier logo]()
$319
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:08 am -
1 stop11h 03m
Thu 11/198:08 pm -
1 stop4h 39m
Deal found 11/2![Frontier logo]()
$320
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 November 4, 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 November 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1510:30 am -
1 stop21h 15m
Wed 11/189:44 am -
1 stop27h 03m
Deal found 10/30![Multiple Airlines logo]()
$367
This United Airlines deal was found by Cheapflights users on 11/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/88:52 am -
1 stop5h 11m
Fri 12/117:30 am -
Nonstop2h 49m
Deal found 11/1![United Airlines logo]()
$367
This Southwest deal was found by Cheapflights users on 11/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/510:15 am -
1 stop6h 35m
Mon 12/71:30 pm -
Nonstop2h 25m
Deal found 11/1![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 11/3. 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 12/46:49 am -
1 stop4h 04m
Tue 12/88:35 am -
1 stop4h 49m
Deal found 11/3![Delta logo]()
$377
This JetBlue deal was found by Cheapflights users on 11/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:00 am -
1 stop8h 55m
Fri 11/204:00 pm -
1 stop8h 38m
Deal found 11/3![JetBlue logo]()
$416
This KAYAK deal was found by Cheapflights users on 11/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/161:29 pm -
Nonstop2h 32m
Sun 11/226:18 pm -
1 stop6h 41m
Deal found 11/2![American Airlines logo]()
$445
This Delta deal was found by Cheapflights users on 11/3. 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 12/511:28 am -
1 stop4h 10m
Sat 12/125:45 pm -
1 stop6h 09m
Deal found 11/3![Delta logo]()
$377
This United Airlines deal was found by Cheapflights users on 10/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:21 pm -
1 stop5h 49m
Fri 11/277:30 am -
Nonstop2h 49m
Deal found 10/30![United Airlines logo]()
$381
This Southwest deal was found by Cheapflights users on 10/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/111:30 am -
2 stops8h 50m
Thu 1/75:55 am -
1 stop7h 25m
Deal found 10/31![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/147:00 am -
1 stop6h 15m
Fri 1/221:25 pm -
Nonstop2h 35m
Deal found 11/3![Southwest logo]()
$384
This United Airlines deal was found by Cheapflights users on 11/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/172:35 pm -
Nonstop2h 32m
Fri 1/227:30 am -
Nonstop2h 48m
Deal found 11/2![United Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 10/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/710:05 am -
2 stops7h 25m
Tue 1/1211:05 am -
2 stops7h 30m
Deal found 10/31![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 11/3. 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 3/911:10 am -
1 stop4h 07m
Mon 3/158:10 pm -
1 stop4h 40m
Deal found 11/3![Delta logo]()
$431
This United Airlines deal was found by Cheapflights users on 11/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/285:59 pm -
Nonstop2h 33m
Sun 1/314:58 pm -
Nonstop2h 52m
Deal found 11/3![United Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 11/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/281:25 pm -
Nonstop2h 15m
Sun 1/317:00 pm -
Nonstop2h 30m
Deal found 11/3![Southwest logo]()
$393
This United Airlines deal was found by Cheapflights users on 10/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/305:53 pm -
Nonstop2h 15m
Tue 4/67:49 am -
Nonstop2h 34m
Deal found 10/30![United Airlines logo]()
$411
This Delta deal was found by Cheapflights users on 10/30. 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.
Thu 11/198:04 am -
1 stop4h 18m
Mon 11/236:10 am -
1 stop4h 15m
Deal found 10/30![Delta logo]()
$463
This United Airlines deal was found by Cheapflights users on 11/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/285:59 pm -
Nonstop2h 43m
Wed 12/307:09 am -
Nonstop2h 51m
Deal found 11/1![United Airlines logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:45 pm -
2 stops36h 34m
Sat 1/29:44 am -
1 stop26h 53m
Deal found 10/31![Multiple Airlines logo]()
$619
This Southwest deal was found by Cheapflights users on 10/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/287:00 pm -
Nonstop2h 15m
Thu 12/315:40 pm -
1 stop4h 50m
Deal found 10/30![Southwest logo]()
$453
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1412:44 pm -
2 stops18h 49m
Wed 11/189:44 am -
1 stop27h 03m
Deal found 10/30![Multiple Airlines logo]()
$622
This United Airlines deal was found by Cheapflights users on 11/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/298:00 pm -
Nonstop2h 42m
Mon 12/77:10 pm -
1 stop5h 19m
Deal found 11/2![United Airlines logo]()
$442
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/110:45 am -
1 stop19h 58m
Sun 4/48:24 pm -
2 stops22h 15m
Deal found 11/4![Multiple Airlines logo]()
$734
Last-minute flights from Chicago to JacksonvilleDiscover last-minute flight deals from Chicago to Jacksonville. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Jacksonville. Data last updated November 4, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 10/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:08 am -
1 stop11h 03m
Sat 11/147:16 pm -
1 stop5h 31m
Deal found 10/31![Frontier logo]()
$312
This Trip.com deal was found by Cheapflights users on 10/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:08 am -
1 stop11h 03m
Sun 11/157:03 pm -
1 stop5h 44m
Deal found 10/31![Frontier logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:55 am -
1 stop23h 50m
Sat 11/147:16 pm -
1 stop14h 44m
Deal found 11/1![Multiple Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:55 am -
1 stop23h 50m
Sun 11/157:03 pm -
1 stop15h 11m
Deal found 11/1![Multiple Airlines logo]()
$309
This Expedia deal was found by Cheapflights users on 11/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:00 am -
1 stop11h 57m
Sun 11/225:59 pm -
1 stop6h 19m
Deal found 11/3![Multiple Airlines logo]()
$317
This CheapOair deal was found by Cheapflights users on 11/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:00 am -
1 stop11h 57m
Fri 11/205:59 pm -
1 stop6h 19m
Deal found 11/3![Multiple Airlines logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:19 am -
1 stop8h 04m
Tue 12/13:20 pm -
2 stops25h 50m
Deal found 11/1![Multiple Airlines logo]()
$307
This Frontier deal was found by Cheapflights users on 11/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:49 am -
1 stop8h 18m
Fri 11/275:59 pm -
1 stop6h 19m
Deal found 11/1![Frontier logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:49 am -
1 stop8h 18m
Mon 11/303:56 pm -
2 stops54h 39m
Deal found 11/2![Multiple Airlines logo]()
$311
This Cheapflightsfares deal was found by Cheapflights users on 10/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:49 am -
1 stop8h 18m
Mon 11/305:59 pm -
1 stop6h 19m
Deal found 10/31![Frontier logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1010:29 pm -
1 stop17h 33m
Sun 12/133:05 pm -
2 stops17h 15m
Deal found 10/31![Multiple Airlines logo]()
$306
This Frontier deal was found by Cheapflights users on 11/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/231:11 pm -
1 stop5h 40m
Fri 1/18:36 pm -
1 stop4h 25m
Deal found 11/1![Frontier logo]()
$318
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 November 4, 2026.
Search for one-way flight options from Chicago to Jacksonville. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This CheapOair deal was found by Cheapflights users on 11/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/27:50 pm -
1 stop18h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![JetBlue logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/33:55 pm -
2 stops24h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$136
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/281:11 pm -
1 stop5h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/318:59 am -
1 stop22h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Multiple Airlines logo]()
$139
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/239:09 am -
1 stop6h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/234:00 pm -
1 stop15h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$141
This Booking.com deal was found by Cheapflights users on 11/3. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:24 pm -
2 stops22h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$142
This Booking.com deal was found by Cheapflights users on 11/3. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/68:37 pm -
2 stops19h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/146:10 am -
2 stops11h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$143
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:05 am -
1 stop10h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$144
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:15 am -
1 stop10h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$144
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:49 am -
1 stop8h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$145
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 (JAX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $306 (Kiwi.com) |
One-way from | $134 (CheapOair) |
Popular in | November |
Cheapest in | January |
Average price | $463 |
Good round-trip deal | $343 or less |
Good one-way deal | $205 or less |
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 November 4, 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
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Sun 12/6
8:37 pm-5:02 pm
2 stops19h 25m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$142
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Mon 12/21
1:11 pm-7:51 pm
1 stop5h 40m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$142
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Wed 12/30
8:35 pm-8:28 pm
2 stops22h 53m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$166
ChicagoJacksonville
ORD Chicago O'Hare Intl - JAX Jacksonville
ORDJAX
Chicago O'Hare Intl
Sat 1/16
7:00 am-3:29 pm
1 stop7h 29m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoJacksonville
ORD Chicago O'Hare Intl - JAX Jacksonville
ORDJAX
Chicago O'Hare Intl
Thu 1/14
2:20 pm-5:52 pm
Nonstop2h 32m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoJacksonville
ORD Chicago O'Hare Intl - JAX Jacksonville
ORDJAX
Chicago O'Hare Intl
Sat 11/21
8:00 pm-11:42 pm
Nonstop2h 42m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoJacksonville
ORD Chicago O'Hare Intl - JAX Jacksonville
ORDJAX
Chicago O'Hare Intl
Mon 12/21
2:30 pm-6:02 pm
Nonstop2h 32m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoJacksonville
RFD Chicago Greater Rockford - JAX Jacksonville
RFDJAX
Chicago Greater Rockford
Wed 12/9
4:01 pm-5:02 pm
3 stops48h 01m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$187
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Sat 11/21
8:42 pm-8:28 pm
2 stops22h 46m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$188
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Sat 12/12
11:28 am-7:05 pm
1 stop6h 37m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$189
Showing 1-10 of 53 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Jacksonville flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Jacksonville flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Jacksonville flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Jacksonville 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 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-JAX
ORD-JAX
MDW-JAX
RFD-JAX
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-JAX
ORD-JAX
MDW-JAX
RFD-JAX
What is the cheapest month to book a flight from Chicago to Jacksonville?
Currently, January is the cheapest month in which you can book a flight from Chicago to Jacksonville (average of $336). Flying from Chicago to Jacksonville in November is currently the most expensive (average of $441). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to JAX?
Find hourly flight availability from Chicago to Jacksonville. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 4, 2026.
It’s typically best to fly out from Chicago to Jacksonville at noon. Doing so could potentially save you 4% on the flight price compared to flying in the evening, which is usually more expensive.
Weekly flight availability from Chicago to Jacksonville
Explore weekly flight availability from Chicago to Jacksonville. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 4, 2026.
The most flights from CHI to JAX are scheduled on a Monday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 on average).
How much does it cost to fly round-trip from Chicago to Jacksonville?
Airfare is below average for this route at the moment.
Chicago to Jacksonville flights typically cost between $357 and $599 in December.The cheapest round-trip price found within the last 5 days was $306 on Multiple Airlines (Dec 10-Dec 13).
How far ahead should I book a flight from Chicago to Jacksonville?
The price you pay for your flight from Chicago to Jacksonville may vary depending on when you book. For the best chance of a lower fare, look to book 80 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Chicago to Jacksonville?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Jacksonville. Price data was last updated on October 31, 2026.
Travelers seeking maximum savings on their Chicago to Jacksonville flight should consider departing on Saturday afternoons when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Chicago to Jacksonville flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Jacksonville trip
Our travel experts
Reviews of airlines servicing Jacksonville
Get insights into the airlines that provide service to Jacksonville. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jacksonville. Reviews last updated November 4, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andJetBlue from Chicago to Jacksonville. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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.
Traveling to a place near Jacksonville?
Book flights to Jacksonville if you plan to visit one of these locationsJacksonville Beach
Fernandina Beach
Orange Park
Kingsland
Waycross
Atlantic Beach
Yulee
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Complete your trip
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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 November 4, 2026.
Chicago and Jacksonville flights
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Top 6 airlines flying from Chicago to Jacksonville
Discover the top 6 airlines 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 November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$83 | Average$274 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$86 | Average$318 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$186 | Average$357 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$236 | Average$349 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$238 | Average$391 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$245 | Average$388 | FlexibilityNo cancel fee | On-time69% |