$140+ Cheap flights from Jacksonville (JAX) to Chicago (CHI)
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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — CHI
Nov 19 — Nov 261
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Jacksonville to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Jacksonville to Chicago are usually found in September or January, booked 88 days in advance, depart on a Thursday or Friday and return on a Saturday
Cheap flight deals from Jacksonville to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Jacksonville to ChicagoExplore the most affordable flight options available from Jacksonville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2026.
Explore the most affordable flight options available from Jacksonville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2026.
This Mytrip deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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.
Thu 11/57:03 pm -
2 stops25h 56m
Mon 11/99:51 am -
2 stops31h 20m
Deal found 10/15![Frontier logo]()
$269
This Expedia deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/257:14 pm -
1 stop28h 07m
Mon 11/3011:53 pm -
1 stop9h 26m
Deal found 10/15![Frontier logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/69:20 pm -
2 stops22h 10m
Wed 11/117:35 pm -
1 stop21h 36m
Deal found 10/15![Multiple Airlines logo]()
$278
This CheapOair deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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.
Thu 11/57:03 pm -
1 stop5h 44m
Sun 11/86:08 am -
1 stop11h 03m
Deal found 10/15![Frontier logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 10/287:03 pm -
1 stop14h 53m
Mon 11/97:50 pm -
1 stop21h 21m
Deal found 10/15![Frontier logo]()
$280
This Mytrip deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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.
Sat 12/53:39 pm -
2 stops10h 15m
Tue 12/85:24 pm -
2 stops19h 56m
Deal found 10/16![Frontier logo]()
$281
This Orbitz deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:14 pm -
1 stop28h 07m
Fri 11/277:49 am -
1 stop8h 18m
Deal found 10/16![Frontier logo]()
$282
This Mytrip deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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.
Thu 11/127:03 pm -
1 stop15h 11m
Thu 11/197:30 pm -
1 stop15h 08m
Deal found 10/14![Multiple Airlines logo]()
$283
This Cheapflightsfares deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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.
Tue 11/245:59 pm -
1 stop6h 19m
Fri 11/277:49 am -
1 stop8h 18m
Deal found 10/16![Frontier logo]()
$284
This Southwest deal was found by Cheapflights users on 10/18. 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 12/910:45 am -
2 stops8h 40m
Mon 12/1412:50 pm -
1 stop4h 30m
Deal found 10/18![Southwest logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/27:03 pm -
1 stop24h 27m
Fri 11/67:49 pm -
1 stop21h 42m
Deal found 10/16![Frontier logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/187:03 pm -
1 stop5h 44m
Sun 11/221:16 pm -
2 stops30h 30m
Deal found 10/19![Multiple Airlines logo]()
$285
Best flights from Jacksonville to ChicagoDiscover carefully curated flight deals from Jacksonville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
Discover carefully curated flight deals from Jacksonville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
This Southwest deal was found by Cheapflights users on 10/19. 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.
Mon 11/163:45 pm -
1 stop6h 45m
Wed 11/186:40 pm -
Nonstop2h 30m
Deal found 10/19![Southwest logo]()
$298
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/1412:35 pm -
Nonstop2h 54m
Mon 11/168:00 pm -
Nonstop2h 42m
Deal found 10/16![United Airlines logo]()
$343
This Mytrip deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/107:03 pm -
2 stops17h 19m
Tue 11/176:08 am -
2 stops25h 16m
Deal found 10/14![Frontier logo]()
$343
This JetBlue deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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.
Fri 12/44:37 pm -
1 stop7h 56m
Mon 12/77:00 am -
1 stop7h 47m
Deal found 10/16![JetBlue logo]()
$353
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 12/412:00 pm -
1 stop7h 01m
Mon 12/79:37 am -
1 stop7h 01m
Deal found 10/15![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 12/187:05 am -
Nonstop2h 30m
Mon 12/217:00 pm -
Nonstop2h 15m
Deal found 10/16![Southwest logo]()
$343
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 12/34:45 pm -
Nonstop2h 49m
Mon 12/75:55 pm -
Nonstop2h 41m
Deal found 10/15![United Airlines logo]()
$391
This Southwest deal was found by Cheapflights users on 10/18. 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 12/236:00 am -
1 stop9h 45m
Tue 12/2912:50 pm -
1 stop9h 15m
Deal found 10/18![Southwest logo]()
$366
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 12/44:45 pm -
Nonstop2h 49m
Mon 12/71:30 pm -
1 stop5h 40m
Deal found 10/14![United Airlines logo]()
$402
This Southwest deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 2/187:30 am -
2 stops8h 30m
Mon 2/225:15 am -
1 stop8h 15m
Deal found 10/16![Southwest logo]()
$368
This JetBlue deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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.
Sun 10/255:46 pm -
1 stop7h 11m
Tue 11/107:00 am -
1 stop8h 14m
Deal found 10/14![JetBlue logo]()
$474
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/57:25 pm -
1 stop4h 50m
Mon 11/92:10 pm -
2 stops8h 35m
Deal found 10/14![Southwest logo]()
$368
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/277:30 am -
Nonstop2h 49m
Sun 11/297:29 am -
Nonstop2h 41m
Deal found 10/15![United Airlines logo]()
$415
This Southwest deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 12/52:10 pm -
1 stop7h 40m
Tue 12/86:40 pm -
Nonstop2h 30m
Deal found 10/16![Southwest logo]()
$398
This United Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 11/254:45 pm -
Nonstop2h 49m
Sun 11/297:29 am -
Nonstop2h 41m
Deal found 10/17![United Airlines logo]()
$449
This Southwest deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 1/221:30 pm -
Nonstop2h 30m
Sun 1/241:30 pm -
Nonstop2h 15m
Deal found 10/15![Southwest logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/283:40 pm -
Nonstop2h 49m
Wed 11/42:29 pm -
Nonstop2h 32m
Deal found 10/14![United Airlines logo]()
$455
This Southwest deal was found by Cheapflights users on 10/18. 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.
Thu 11/1910:45 am -
2 stops8h 40m
Sun 11/227:50 am -
2 stops7h 50m
Deal found 10/18![Southwest logo]()
$403
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:30 am -
Nonstop2h 49m
Sun 12/62:30 pm -
1 stop7h 10m
Deal found 10/19![United Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/169:42 am -
Nonstop2h 54m
Wed 11/188:00 pm -
Nonstop2h 42m
Deal found 10/19![United Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 11/127:10 pm -
1 stop5h 51m
Mon 11/162:29 pm -
Nonstop2h 32m
Deal found 10/17![United Airlines logo]()
$469
Last-minute flights from Jacksonville to ChicagoDiscover last-minute flight deals from Jacksonville to Chicago. Data last updated October 20, 2026 and is based on user searches.
Discover last-minute flight deals from Jacksonville to Chicago. Data last updated October 20, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/267:46 pm -
1 stop18h 05m
Mon 11/910:19 am -
1 stop6h 52m
Deal found 10/14![Frontier logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/277:03 pm -
1 stop18h 48m
Mon 11/910:19 am -
1 stop6h 52m
Deal found 10/14![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/283:55 pm -
2 stops18h 01m
Fri 11/610:19 am -
1 stop8h 06m
Deal found 10/14![Multiple Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/293:00 pm -
1 stop25h 37m
Thu 11/510:19 am -
1 stop6h 52m
Deal found 10/14![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/297:03 pm -
1 stop15h 14m
Tue 11/107:35 pm -
1 stop21h 36m
Deal found 10/14![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/303:56 pm -
2 stops21h 55m
Sat 11/77:05 am -
1 stop10h 26m
Deal found 10/14![Multiple Airlines logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/57:03 pm -
1 stop24h 51m
Sun 11/87:50 pm -
1 stop21h 21m
Deal found 10/14![Frontier logo]()
$271
This CheapOair deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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.
Thu 11/57:03 pm -
1 stop5h 44m
Sun 11/86:08 am -
1 stop11h 03m
Deal found 10/15![Frontier logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/187:03 pm -
1 stop5h 44m
Sun 11/221:16 pm -
2 stops30h 30m
Deal found 10/19![Multiple Airlines logo]()
$285
This Orbitz deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:14 pm -
1 stop28h 07m
Fri 11/277:49 am -
1 stop8h 18m
Deal found 10/16![Frontier logo]()
$282
This Super.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/215:59 pm -
1 stop6h 19m
Mon 11/3011:53 pm -
1 stop9h 26m
Deal found 10/14![Frontier logo]()
$285
This Cheapflightsfares deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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.
Tue 11/245:59 pm -
1 stop6h 19m
Fri 11/277:49 am -
1 stop8h 18m
Deal found 10/14![Frontier logo]()
$274
One-way flights from Jacksonville to ChicagoSearch for one-way flight options from Jacksonville to Chicago. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
Search for one-way flight options from Jacksonville to Chicago. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
This Southwest deal was found by Cheapflights users on 10/18. 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 12/98:45 am -
1 stop9h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Southwest logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 11/147:16 pm -
1 stop14h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/283:55 pm -
1 stop24h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 10/298:36 pm -
1 stop18h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Allegiant Air logo]()
$144
This Super.com deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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.
Mon 11/305:59 pm -
1 stop6h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$146
This Trip.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 1/48:36 pm -
1 stop4h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$146
This Super.com deal was found by Cheapflights users on 10/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:08 pm -
1 stop5h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$147
This Super.com deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 10/247:46 pm -
1 stop4h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 12/13:20 pm -
2 stops23h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$148
This Super.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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.
Tue 10/277:03 pm -
1 stop5h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$148
This Frontier deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 12/232:55 pm -
1 stop6h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$149
This Frontier deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 12/288:36 pm -
1 stop4h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$149
Find flight deals from Jacksonville to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Jacksonville (JAX) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $269 (Kiwi.com) |
One-way from | $140 (Southwest) |
Popular in | May |
Cheapest in | September |
Average price | $327 |
Good round-trip deal | $372 or less |
Good one-way deal | $249 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Jacksonville to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 20, 2026.
Use the filters below to find and compare flights from Jacksonville to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Thu 1/14
7:50 am-2:45 pm
2 stops7h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$145
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Mon 11/30
5:59 pm-11:18 pm
1 stop6h 19m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$146
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Mon 11/9
7:20 am-8:50 am
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Sun 1/24
6:25 pm-11:50 am
2 stops42h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$160
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Sat 12/5
7:30 am-9:19 am
Nonstop2h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$172
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Tue 2/2
9:48 am-11:40 am
Nonstop2h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$172
Quickest round-trip
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Tue 12/15
1:30 pm-2:55 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$172
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Tue 1/5
1:30 pm-2:55 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$172
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Tue 11/10
1:30 pm-2:55 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$172
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Mon 11/23
9:42 am-11:36 am
Nonstop2h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
Showing 1-10 of 43 resultsSorted by cheapest first
Compare providers for flights from Jacksonville to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Jacksonville to Chicago in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Jacksonville-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jacksonville-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Jacksonville-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Jacksonville-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Jacksonville-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Jacksonville to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Jacksonville with our price prediction graph.
JAX-CHI
JAX-ORD
JAX-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Jacksonville to Chicago
JAX-CHI
JAX-ORD
JAX-MDW
What is the cheapest month to book a flight from Jacksonville to Chicago?
Currently, January is the cheapest month in which you can book a flight from Jacksonville to Chicago (average of $309). Flying from Jacksonville to Chicago in November is currently the most expensive (average of $414). 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 JAX to CHI?
Find hourly flight availability from Jacksonville to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 20, 2026.
One of the essential ways to save on airfare from Jacksonville to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 29% on airfare.
Weekly flight availability from Jacksonville to Chicago
Explore weekly flight availability from Jacksonville to Chicago. 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 October 20, 2026.
The most flights from JAX to CHI are scheduled on a Friday (28 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (20 on average).
How much does it cost to fly round-trip from Jacksonville to Chicago?
Airfare is below average for this route at the moment.
Jacksonville to Chicago flights typically cost between $277 and $432 in October.The cheapest round-trip price found within the last 5 days was $269 on Multiple Airlines (Oct 29-Nov 5).
How far ahead should I book a flight from Jacksonville to Chicago?
The price you pay for your flight from Jacksonville to Chicago 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 Jacksonville to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Jacksonville to Chicago. Price data was last updated on October 17, 2026.
Travelers seeking maximum savings on their Jacksonville to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Jacksonville to Chicago 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 Jacksonville to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated October 20, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andJetBlue from Jacksonville to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.4
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.4
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.4
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.4
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.4
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.4
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Jacksonville to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Jacksonville
Popular flights
Alternative routes for Jacksonville to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 20, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Jacksonville to Chicago by cabin class
Find flights from Jacksonville to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Jacksonville and Chicago flights
Browse other Jacksonville and Chicago flight options. Last updated on October 20, 2026.
Other flights from Jacksonville
Browse through other flights departing from Jacksonville. Flights are based on user searches made on Cheapflights and were last updated on October 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Jacksonville to Chicago
Discover the top 6 airlines that operate flights from Jacksonville to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$122 | Average$264 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$128 | Average$309 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$197 | Average$363 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$206 | Average$303 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$217 | Average$369 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$223 | Average$387 | FlexibilityNo cancel fee | On-time69% |