$117+ 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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAX
Oct 23 — Oct 301
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 October, booked 85 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 September 23, 2026.
Explore the most affordable flight options available from Chicago to Jacksonville. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:16 am -
1 stop10h 52m
Mon 11/167:03 pm -
1 stop5h 44m
Deal found 9/20![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/296:00 am -
2 stops11h 08m
Tue 11/37:03 pm -
1 stop18h 48m
Deal found 9/18![Frontier logo]()
$233
This Mytrip deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:16 am -
1 stop10h 52m
Tue 11/177:03 pm -
2 stops17h 19m
Deal found 9/20![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Tue 10/207:40 am -
2 stops10h 06m
Sun 10/256:20 pm -
1 stop16h 01m
Deal found 9/19![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:25 am -
1 stop10h 03m
Tue 11/37:03 pm -
2 stops17h 19m
Deal found 9/21![Frontier logo]()
$236
This Mytrip deal was found by Cheapflights users on 9/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
2 stops11h 31m
Thu 10/297:03 pm -
2 stops21h 34m
Deal found 9/19![Frontier logo]()
$236
This Trip.com deal was found by Cheapflights users on 9/19. 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.
Fri 10/306:16 am -
1 stop10h 52m
Mon 11/27:03 pm -
1 stop5h 44m
Deal found 9/19![Frontier logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/217:40 am -
2 stops10h 06m
Fri 10/237:46 pm -
1 stop16h 46m
Deal found 9/19![Frontier logo]()
$237
This Cheapflightsfares deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:15 am -
1 stop11h 16m
Thu 10/156:20 pm -
1 stop6h 23m
Deal found 9/20![Frontier logo]()
$238
This JetBlue deal was found by Cheapflights users on 9/18. 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 10/147:00 am -
1 stop8h 14m
Tue 10/204:00 pm -
1 stop8h 30m
Deal found 9/18![JetBlue logo]()
$238
This Mytrip deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:04 am -
2 stops32h 21m
Wed 10/287:03 pm -
2 stops21h 34m
Deal found 9/21![Frontier logo]()
$239
This Mytrip deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:21 am -
1 stop11h 25m
Mon 10/267:46 pm -
2 stops16h 36m
Deal found 9/23![Frontier logo]()
$240
Best flights from Chicago to JacksonvilleDiscover carefully curated flight deals from Chicago to Jacksonville that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
Discover carefully curated flight deals from Chicago to Jacksonville that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:40 am -
1 stop22h 05m
Wed 10/283:55 pm -
1 stop17h 55m
Deal found 9/21![Multiple Airlines logo]()
$243
This JetBlue deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:00 am -
1 stop8h 14m
Mon 10/195:10 pm -
1 stop7h 20m
Deal found 9/21![JetBlue logo]()
$316
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:30 pm -
Nonstop2h 32m
Tue 11/39:42 am -
Nonstop2h 54m
Deal found 9/21![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 9/19. 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 10/1010:30 am -
Nonstop2h 15m
Sun 10/118:55 pm -
1 stop4h 15m
Deal found 9/19![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 9/18. 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 12/91:30 pm -
1 stop4h 45m
Tue 1/55:30 am -
1 stop4h 04m
Deal found 9/18![Delta logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1810:30 am -
1 stop21h 00m
Sat 10/313:55 pm -
1 stop19h 35m
Deal found 9/21![Multiple Airlines logo]()
$269
This JetBlue deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:00 am -
1 stop8h 14m
Tue 10/204:00 pm -
1 stop8h 30m
Deal found 9/20![JetBlue logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:40 am -
1 stop22h 05m
Sat 10/313:55 pm -
1 stop19h 35m
Deal found 9/21![Multiple Airlines logo]()
$289
This JetBlue deal was found by Cheapflights users on 9/19. 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 10/217:00 am -
1 stop8h 14m
Mon 10/265:46 pm -
1 stop7h 11m
Deal found 9/19![JetBlue logo]()
$316
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:16 am -
Nonstop2h 35m
Tue 10/2012:40 pm -
1 stop7h 01m
Deal found 9/22![United Airlines logo]()
$367
This Southwest deal was found by Cheapflights users on 9/18. 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.
Wed 12/166:00 am -
1 stop6h 15m
Mon 12/217:05 am -
Nonstop2h 30m
Deal found 9/18![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 9/18. 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 12/217:00 pm -
Nonstop2h 10m
Sat 1/236:40 am -
2 stops8h 40m
Deal found 9/18![Southwest logo]()
$372
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/208:05 am -
1 stop6h 52m
Sat 1/238:30 am -
1 stop5h 50m
Deal found 9/20![Delta logo]()
$432
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/228:00 am -
Nonstop2h 25m
Fri 12/251:30 pm -
Nonstop2h 25m
Deal found 9/23![Southwest logo]()
$374
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/82:29 pm -
Nonstop2h 32m
Thu 11/124:45 pm -
Nonstop2h 49m
Deal found 9/22![United Airlines logo]()
$412
This JetBlue deal was found by Cheapflights users on 9/19. 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.
Tue 10/610:59 am -
1 stop6h 11m
Tue 10/134:00 pm -
1 stop8h 30m
Deal found 9/19![JetBlue logo]()
$420
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:55 am -
1 stop6h 05m
Mon 12/73:45 pm -
2 stops7h 55m
Deal found 9/22![Southwest logo]()
$382
This United Airlines deal was found by Cheapflights users on 9/18. 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.
Wed 11/118:00 pm -
Nonstop2h 42m
Sun 11/157:11 am -
Nonstop2h 49m
Deal found 9/18![United Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:35 am -
2 stops8h 25m
Sat 11/213:40 pm -
2 stops9h 45m
Deal found 9/20![Southwest logo]()
$387
This United Airlines deal was found by Cheapflights users on 9/18. 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 11/1310:44 am -
Nonstop2h 36m
Sun 11/157:11 am -
Nonstop2h 49m
Deal found 9/18![United Airlines logo]()
$427
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/49:36 pm -
2 stops20h 25m
Wed 10/73:55 pm -
1 stop17h 55m
Deal found 9/20![Multiple Airlines logo]()
$494
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:40 pm -
Nonstop2h 30m
Sun 11/157:20 am -
Nonstop2h 30m
Deal found 9/20![Southwest logo]()
$397
This Southwest deal was found by Cheapflights users on 9/19. 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 11/62:10 pm -
2 stops8h 35m
Mon 11/92:10 pm -
2 stops6h 55m
Deal found 9/19![Southwest logo]()
$411
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1810:30 am -
1 stop21h 00m
Sun 10/254:13 pm -
2 stops45h 39m
Deal found 9/21![Multiple Airlines logo]()
$571
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/87:00 pm -
Nonstop2h 20m
Thu 11/127:20 am -
Nonstop2h 30m
Deal found 9/22![Southwest logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2212:37 pm -
2 stops27h 30m
Wed 12/29:44 am -
1 stop27h 13m
Deal found 9/22![Multiple Airlines logo]()
$593
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:35 am -
1 stop7h 00m
Sun 11/157:05 pm -
Nonstop2h 35m
Deal found 9/22![Southwest logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:37 pm -
2 stops27h 30m
Wed 12/29:44 am -
1 stop27h 13m
Deal found 9/22![Multiple Airlines logo]()
$649
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:07 pm -
2 stops42h 18m
Wed 12/29:44 am -
1 stop27h 13m
Deal found 9/22![Multiple Airlines logo]()
$722
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:42 am -
2 stops25h 38m
Sat 10/103:55 pm -
1 stop18h 45m
Deal found 9/22![Multiple Airlines logo]()
$825
Last-minute flights from Chicago to JacksonvilleDiscover last-minute flight deals from Chicago to Jacksonville. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Jacksonville. Data last updated September 23, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 9/18. 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.
Sun 10/116:24 am -
1 stop10h 01m
Mon 10/127:46 pm -
1 stop4h 57m
Deal found 9/18![Frontier logo]()
$234
This Cheapflightsfares deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:15 am -
1 stop11h 16m
Thu 10/156:20 pm -
1 stop6h 23m
Deal found 9/20![Frontier logo]()
$238
This Mytrip deal was found by Cheapflights users on 9/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
2 stops11h 31m
Thu 10/297:03 pm -
2 stops21h 34m
Deal found 9/19![Frontier logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Tue 10/207:40 am -
2 stops10h 06m
Sun 10/256:20 pm -
1 stop16h 01m
Deal found 9/19![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Tue 10/207:40 am -
2 stops10h 06m
Thu 10/297:03 pm -
1 stop15h 14m
Deal found 9/19![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/217:40 am -
2 stops10h 06m
Fri 10/237:46 pm -
1 stop16h 46m
Deal found 9/19![Frontier logo]()
$237
This Mytrip deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:04 am -
2 stops32h 21m
Wed 10/287:03 pm -
2 stops21h 34m
Deal found 9/21![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:01 pm -
2 stops21h 45m
Mon 10/267:46 pm -
1 stop18h 05m
Deal found 9/21![Frontier logo]()
$240
This Frontier deal was found by Cheapflights users on 9/18. 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 10/286:16 am -
1 stop10h 52m
Fri 10/307:03 pm -
1 stop5h 44m
Deal found 9/18![Frontier logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/296:00 am -
2 stops11h 08m
Tue 11/37:03 pm -
1 stop18h 48m
Deal found 9/18![Frontier logo]()
$233
This Trip.com deal was found by Cheapflights users on 9/19. 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.
Fri 10/306:16 am -
1 stop10h 52m
Mon 11/27:03 pm -
1 stop5h 44m
Deal found 9/19![Frontier logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:25 am -
1 stop10h 03m
Tue 11/37:03 pm -
2 stops17h 19m
Deal found 9/21![Frontier logo]()
$236
One-way flights from Chicago to JacksonvilleSearch for one-way flight options from Chicago to Jacksonville. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
Search for one-way flight options from Chicago to Jacksonville. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:07 am -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$117
This Frontier deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:26 am -
1 stop6h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/228:10 am -
1 stop11h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$118
This Mytrip deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:04 am -
2 stops32h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1910:26 am -
1 stop7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$121
This Frontier deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:16 am -
1 stop10h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$122
This Cheapflightsfares deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1210:26 am -
1 stop7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:44 pm -
1 stop21h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:40 am -
2 stops10h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$126
This Super.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:07 am -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:15 am -
1 stop11h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:00 am -
2 stops10h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$130
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 September 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $233 (Kiwi.com) |
One-way from | $117 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $379 |
Good round-trip deal | $282 or less |
Good one-way deal | $143 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 September 23, 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
RFD Chicago Greater Rockford - JAX Jacksonville
RFDJAX
Chicago Greater Rockford
Thu 11/5
9:30 am-6:08 pm
2 stops31h 38m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$136
ChicagoJacksonville
RFD Chicago Greater Rockford - JAX Jacksonville
RFDJAX
Chicago Greater Rockford
Thu 11/12
9:30 am-6:08 pm
2 stops31h 38m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$143
ChicagoJacksonville
RFD Chicago Greater Rockford - JAX Jacksonville
RFDJAX
Chicago Greater Rockford
Thu 10/22
9:40 am-8:45 am
1 stop22h 05m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$147
Quickest round-trip
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Sat 10/24
10:30 am-1:45 pm
Nonstop2h 15m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
ChicagoJacksonville
ORD Chicago O'Hare Intl - JAX Jacksonville
ORDJAX
Chicago O'Hare Intl
Sat 10/17
9:38 am-7:32 pm
1 stop8h 54m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
ChicagoJacksonville
ORD Chicago O'Hare Intl - JAX Jacksonville
ORDJAX
Chicago O'Hare Intl
Mon 10/19
6:05 pm-9:47 pm
Nonstop2h 42m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Mon 10/19
2:55 pm-6:15 pm
Nonstop2h 20m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
ChicagoJacksonville
ORD Chicago O'Hare Intl - JAX Jacksonville
ORDJAX
Chicago O'Hare Intl
Sat 10/24
3:35 pm-7:09 pm
Nonstop2h 34m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
ChicagoJacksonville
ORD Chicago O'Hare Intl - JAX Jacksonville
ORDJAX
Chicago O'Hare Intl
Wed 10/21
7:00 am-4:14 pm
1 stop8h 14m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Thu 11/12
12:50 pm-4:05 pm
Nonstop2h 15m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
Showing 1-10 of 60 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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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
MDW-JAX
ORD-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
MDW-JAX
ORD-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 $334). Flying from Chicago to Jacksonville in December is currently the most expensive (average of $412). 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 September 23, 2026.
It’s typically best to fly out from Chicago to Jacksonville at noon. Doing so could potentially save you 7% 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 September 23, 2026.
The most flights from CHI to JAX are scheduled on a Tuesday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 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 $270 and $471 in November.The cheapest round-trip price found within the last 5 days was $233 on Frontier (Nov 12-Nov 16).
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 87 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 September 19, 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 September 23, 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.
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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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Other flights to Jacksonville
Explore flights to Jacksonville departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 23, 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 September 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$83 | Average$274 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$86 | Average$262 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$186 | Average$355 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$225 | Average$389 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$236 | Average$349 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$243 | Average$379 | FlexibilityNo cancel fee | On-time69% |