$118+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — CHI
Oct 23 — Oct 301
Round-trip
1 adult, Economy
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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 October or September, booked 76 days in advance, depart on a Thursday or Friday and return on a Saturday
Cheap flight deals from Jacksonville to Chicago
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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 September 23, 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 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.
Tue 10/207:46 pm -
1 stop16h 46m
Tue 10/277:15 am -
1 stop9h 53m
Deal found 9/21![Frontier logo]()
$198
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:03 pm -
1 stop5h 44m
Tue 11/36:16 am -
1 stop10h 52m
Deal found 9/19![Frontier logo]()
$198
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 10/277:03 pm -
1 stop18h 48m
Sat 10/317:15 am -
1 stop10h 13m
Deal found 9/19![Frontier logo]()
$199
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.
Wed 10/217:46 pm -
1 stop23h 45m
Wed 10/287:15 am -
1 stop9h 53m
Deal found 9/21![Frontier logo]()
$200
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:03 pm -
1 stop5h 44m
Sat 11/77:25 am -
1 stop10h 03m
Deal found 9/21![Frontier logo]()
$200
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:46 pm -
1 stop4h 57m
Sat 10/246:21 am -
1 stop11h 25m
Deal found 9/19![Frontier logo]()
$201
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 12/35:55 pm -
1 stop14h 10m
Mon 12/76:10 am -
1 stop26h 35m
Deal found 9/18![Multiple Airlines logo]()
$202
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.
Wed 12/94:00 pm -
1 stop22h 59m
Tue 12/228:10 am -
1 stop11h 19m
Deal found 9/18![Multiple Airlines logo]()
$203
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.
Thu 10/156:20 pm -
1 stop6h 23m
Mon 10/196:15 am -
1 stop11h 16m
Deal found 9/18![Frontier logo]()
$203
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 10/277:03 pm -
1 stop18h 48m
Wed 10/287:28 pm -
1 stop21h 40m
Deal found 9/22![Frontier logo]()
$205
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:20 pm -
1 stop6h 23m
Mon 10/266:15 am -
1 stop11h 16m
Deal found 9/20![Frontier logo]()
$205
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 10/207:46 pm -
1 stop16h 46m
Fri 10/237:44 pm -
1 stop22h 02m
Deal found 9/19![Frontier logo]()
$206
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 September 23, 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 September 23, 2026.
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:13 am -
Nonstop2h 49m
Sat 11/78:00 pm -
Nonstop2h 42m
Deal found 9/19![United Airlines logo]()
$327
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 11/57:20 am -
Nonstop2h 30m
Mon 11/97:00 pm -
Nonstop2h 20m
Deal found 9/20![Southwest logo]()
$327
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.
Fri 10/164:58 pm -
Nonstop2h 48m
Mon 10/196:05 pm -
Nonstop2h 42m
Deal found 9/21![United Airlines logo]()
$327
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:45 pm -
Nonstop2h 20m
Wed 10/286:00 pm -
Nonstop2h 20m
Deal found 9/21![Southwest logo]()
$327
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:40 am -
Nonstop2h 46m
Mon 10/196:05 pm -
Nonstop2h 42m
Deal found 9/20![United Airlines logo]()
$327
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:20 am -
Nonstop2h 30m
Mon 11/97:00 pm -
Nonstop2h 20m
Deal found 9/21![Southwest logo]()
$327
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.
Tue 10/134:58 pm -
Nonstop2h 48m
Thu 10/153:35 pm -
Nonstop2h 34m
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 10/172:25 pm -
1 stop6h 10m
Sat 10/2410:30 am -
Nonstop2h 15m
Deal found 9/19![Southwest logo]()
$337
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 10/102:25 pm -
1 stop6h 10m
Wed 10/146:00 pm -
Nonstop2h 20m
Deal found 9/19![Southwest logo]()
$337
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 12/39:40 am -
Nonstop2h 54m
Sat 12/510:50 am -
Nonstop2h 35m
Deal found 9/22![United Airlines logo]()
$357
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 11/41:30 pm -
Nonstop2h 25m
Sat 11/76:35 am -
1 stop5h 55m
Deal found 9/20![Southwest logo]()
$337
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.
Wed 11/1112:35 pm -
Nonstop2h 54m
Wed 11/118:00 pm -
Nonstop2h 42m
Deal found 9/22![United Airlines logo]()
$357
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.
Thu 12/177:05 pm -
Nonstop2h 30m
Mon 12/217:00 pm -
Nonstop2h 10m
Deal found 9/18![Southwest logo]()
$357
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 12/31:30 pm -
Nonstop2h 25m
Sat 12/57:35 am -
1 stop7h 00m
Deal found 9/22![Southwest logo]()
$367
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.
Tue 10/207:10 pm -
1 stop4h 05m
Tue 10/276:00 pm -
Nonstop2h 20m
Deal found 9/22![Southwest logo]()
$367
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.
Sat 12/127:30 am -
Nonstop2h 49m
Fri 12/182:30 pm -
Nonstop2h 32m
Deal found 9/22![United Airlines logo]()
$474
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.
Fri 10/94:58 pm -
Nonstop2h 48m
Mon 10/127:05 am -
Nonstop2h 46m
Deal found 9/22![United Airlines logo]()
$553
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.
Fri 9/257:20 pm -
1 stop17h 28m
Sat 9/263:35 pm -
Nonstop2h 34m
Deal found 9/21![United Airlines logo]()
$559
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.
Wed 9/3012:40 pm -
Nonstop2h 53m
Sun 10/410:16 am -
Nonstop2h 35m
Deal found 9/21![United Airlines logo]()
$562
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 10/23:39 pm -
1 stop6h 53m
Mon 10/56:05 pm -
Nonstop2h 42m
Deal found 9/18![United Airlines logo]()
$563
Last-minute flights from Jacksonville to ChicagoDiscover last-minute flight deals from Jacksonville to Chicago. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Jacksonville to Chicago. Data last updated September 23, 2026 and is based on user searches.
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.
Fri 10/23:46 pm -
1 stop24h 34m
Tue 10/67:11 am -
1 stop24h 19m
Deal found 9/18![Multiple Airlines logo]()
$271
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.
Fri 10/23:46 pm -
1 stop24h 34m
Mon 10/57:28 pm -
1 stop22h 33m
Deal found 9/18![Multiple Airlines logo]()
$316
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:46 pm -
2 stops20h 34m
Tue 10/66:20 am -
1 stop11h 41m
Deal found 9/18![Frontier logo]()
$320
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.
Sat 10/107:46 pm -
1 stop4h 57m
Wed 10/146:21 am -
1 stop11h 25m
Deal found 9/19![Frontier logo]()
$209
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.
Thu 10/156:20 pm -
1 stop6h 23m
Mon 10/196:15 am -
1 stop11h 16m
Deal found 9/18![Frontier logo]()
$203
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:20 pm -
1 stop6h 23m
Wed 10/216:21 am -
1 stop11h 25m
Deal found 9/20![Frontier logo]()
$206
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.
Fri 10/167:46 pm -
1 stop4h 57m
Mon 10/196:15 am -
1 stop11h 16m
Deal found 9/18![Frontier logo]()
$216
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:46 pm -
1 stop4h 57m
Sat 10/246:21 am -
1 stop11h 25m
Deal found 9/19![Frontier logo]()
$201
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:20 pm -
1 stop6h 23m
Mon 10/266:15 am -
1 stop11h 16m
Deal found 9/20![Frontier logo]()
$205
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 10/226:20 pm -
1 stop6h 23m
Tue 10/279:53 am -
1 stop7h 15m
Deal found 9/20![Frontier logo]()
$220
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:03 pm -
1 stop5h 44m
Tue 11/36:16 am -
1 stop10h 52m
Deal found 9/19![Frontier logo]()
$198
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:03 pm -
1 stop5h 44m
Sat 11/77:25 am -
1 stop10h 03m
Deal found 9/21![Frontier logo]()
$200
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 September 23, 2026.
Search for one-way flight options from Jacksonville to Chicago. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:03 pm -
2 stops21h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$118
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.
Mon 10/197:46 pm -
1 stop28h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Frontier logo]()
$118
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.
Mon 10/197:46 pm -
1 stop23h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$119
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.
Wed 12/164:00 pm -
1 stop21h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$122
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.
Sat 10/175:50 pm -
1 stop6h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![JetBlue logo]()
$123
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:20 pm -
1 stop6h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$123
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.
Tue 10/63:20 pm -
1 stop25h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$124
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 11/225:59 pm -
1 stop14h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![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.
Sun 10/256:20 pm -
1 stop16h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$125
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 10/237:46 pm -
1 stop28h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$125
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 11/187:03 pm -
2 stops17h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$126
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:46 pm -
2 stops20h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Frontier logo]()
$127
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 September 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $198 (Kiwi.com) |
One-way from | $118 (Mytrip) |
Popular in | May |
Cheapest in | October |
Average price | $307 |
Good round-trip deal | $336 or less |
Good one-way deal | $168 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 September 23, 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 - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Thu 10/29
9:35 am-11:29 am
Nonstop2h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
Quickest round-trip
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Tue 10/27
12:45 pm-2:05 pm
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Fri 11/13
7:30 am-9:19 am
Nonstop2h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Wed 11/18
1:30 pm-2:55 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Tue 10/27
7:30 am-9:19 am
Nonstop2h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Thu 10/22
4:58 pm-6:46 pm
Nonstop2h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Wed 10/21
12:45 pm-2:05 pm
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Thu 12/17
7:05 pm-8:35 pm
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Tue 11/17
12:35 pm-2:29 pm
Nonstop2h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Tue 12/1
7:30 am-9:19 am
Nonstop2h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
Showing 1-10 of 41 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 September.
| 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-MDW
JAX-ORD
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-MDW
JAX-ORD
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 $384). 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 September 23, 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 28% 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 September 23, 2026.
The most flights from JAX to CHI are scheduled on a Monday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 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 $240 and $402 in October.The cheapest round-trip price found within the last 5 days was $198 on Frontier (Oct 20-Oct 27).
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 September 19, 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. Monday 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 September 23, 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.
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
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
Lansing
Merrillville
Valparaiso
Hammond
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Porter
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Other flights to Chicago
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Jacksonville and Chicago flights
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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 September 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$121 | Average$283 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$134 | Average$247 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$197 | Average$377 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$206 | Average$303 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$217 | Average$367 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$222 | Average$380 | FlexibilityNo cancel fee | On-time69% |