$99+ Cheap flights from Chicago (CHI) to Jacksonville (JAX)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAX
Sep 3 — Sep 101
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 August or January, booked 81 days in advance, depart on a Saturday or Tuesday and return on a Thursday
Cheap flight deals from Chicago to Jacksonville
Cheapest
Best
Last-minute
One-way
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 August 4, 2026.
Explore the most affordable flight options available from Chicago to Jacksonville. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:28 pm -
1 stop22h 33m
Sat 9/197:46 pm -
1 stop14h 34m
Deal found 8/3![Frontier logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:28 pm -
1 stop22h 33m
Sat 10/37:46 pm -
1 stop14h 34m
Deal found 8/3![Frontier logo]()
$204
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:35 pm -
Nonstop2h 44m
Fri 9/1111:51 am -
1 stop7h 46m
Deal found 8/4![United Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:11 am -
1 stop24h 14m
Fri 9/117:46 pm -
1 stop17h 05m
Deal found 8/4![Multiple Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:59 pm -
1 stop27h 11m
Fri 9/113:41 pm -
1 stop24h 39m
Deal found 8/4![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:14 am -
1 stop7h 11m
Mon 9/77:05 pm -
1 stop13h 48m
Deal found 8/2![Multiple Airlines logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/251:59 pm -
1 stop27h 11m
Sat 8/297:05 pm -
1 stop13h 48m
Deal found 8/3![Frontier logo]()
$212
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:45 am -
2 stops6h 45m
Sun 9/64:45 pm -
Nonstop2h 20m
Deal found 7/31![Southwest logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:26 am -
1 stop7h 35m
Mon 9/217:46 pm -
2 stops19h 31m
Deal found 8/2![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:20 am -
2 stops11h 41m
Sun 9/207:46 pm -
1 stop14h 34m
Deal found 8/2![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:05 am -
1 stop7h 20m
Sun 9/67:05 pm -
1 stop13h 48m
Deal found 8/2![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:11 am -
1 stop24h 14m
Sat 9/197:46 pm -
1 stop14h 34m
Deal found 8/1![Multiple Airlines logo]()
$216
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 August 4, 2026.
Discover carefully curated flight deals from Chicago to Jacksonville that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 4, 2026.
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/223:00 pm -
Nonstop2h 15m
Mon 11/25:20 pm -
2 stops7h 45m
Deal found 7/30![Southwest logo]()
$212
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:40 am -
1 stop5h 56m
Sat 9/121:02 pm -
1 stop4h 35m
Deal found 7/30![Delta logo]()
$217
This JetBlue deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:00 am -
1 stop6h 40m
Sun 9/67:10 am -
1 stop7h 39m
Deal found 7/31![JetBlue logo]()
$255
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:56 pm -
1 stop6h 58m
Mon 8/247:30 am -
Nonstop2h 48m
Deal found 7/30![United Airlines logo]()
$288
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/249:20 am -
1 stop6h 45m
Thu 8/274:30 pm -
2 stops7h 50m
Deal found 7/30![Southwest logo]()
$222
This JetBlue deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:00 pm -
1 stop6h 29m
Sun 9/207:19 am -
1 stop7h 26m
Deal found 8/1![JetBlue logo]()
$268
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/283:35 pm -
Nonstop2h 34m
Thu 10/19:40 am -
Nonstop2h 46m
Deal found 8/4![United Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:05 am -
1 stop6h 16m
Sat 9/266:59 pm -
1 stop4h 45m
Deal found 8/3![Delta logo]()
$325
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:29 am -
Nonstop2h 35m
Sat 8/2912:37 pm -
Nonstop2h 53m
Deal found 8/3![United Airlines logo]()
$305
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:30 am -
1 stop7h 25m
Wed 9/235:25 pm -
Nonstop2h 25m
Deal found 8/2![Southwest logo]()
$315
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1210:30 am -
Nonstop2h 35m
Sat 9/194:45 pm -
Nonstop2h 49m
Deal found 8/2![United Airlines logo]()
$305
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:25 am -
2 stops7h 10m
Thu 9/37:50 am -
2 stops8h 05m
Deal found 7/30![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:45 pm -
Nonstop2h 20m
Sun 9/1311:20 am -
1 stop4h 05m
Deal found 8/3![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1812:55 pm -
1 stop6h 59m
Sat 9/197:15 am -
Nonstop2h 48m
Deal found 8/3![United Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:40 am -
2 stops9h 25m
Sat 9/194:10 pm -
1 stop4h 10m
Deal found 8/2![Southwest logo]()
$330
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/912:55 pm -
1 stop6h 59m
Mon 10/129:40 am -
Nonstop2h 46m
Deal found 7/31![United Airlines logo]()
$346
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/133:35 pm -
Nonstop2h 34m
Sun 10/189:40 am -
Nonstop2h 46m
Deal found 8/3![United Airlines logo]()
$366
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:55 pm -
Nonstop2h 42m
Mon 8/247:30 am -
Nonstop2h 48m
Deal found 7/31![United Airlines logo]()
$388
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:55 pm -
1 stop6h 59m
Tue 9/227:30 am -
Nonstop2h 48m
Deal found 8/3![United Airlines logo]()
$391
Last-minute flights from Chicago to JacksonvilleDiscover last-minute flight deals from Chicago to Jacksonville. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Jacksonville. Data last updated August 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/251:59 pm -
1 stop27h 11m
Sat 8/297:05 pm -
1 stop13h 48m
Deal found 8/3![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:14 am -
1 stop7h 11m
Mon 9/77:05 pm -
1 stop13h 48m
Deal found 8/2![Multiple Airlines logo]()
$211
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:35 pm -
Nonstop2h 44m
Fri 9/1111:51 am -
1 stop7h 46m
Deal found 8/4![United Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:59 pm -
1 stop27h 11m
Fri 9/113:41 pm -
1 stop24h 39m
Deal found 8/4![Multiple Airlines logo]()
$210
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:45 am -
2 stops6h 45m
Sun 9/64:45 pm -
Nonstop2h 20m
Deal found 7/31![Southwest logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:05 am -
1 stop7h 20m
Sun 9/67:05 pm -
1 stop13h 48m
Deal found 8/2![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:11 am -
1 stop24h 14m
Fri 9/117:46 pm -
1 stop17h 05m
Deal found 8/4![Multiple Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:11 am -
1 stop24h 14m
Sat 9/197:46 pm -
1 stop14h 34m
Deal found 8/1![Multiple Airlines logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:28 pm -
1 stop22h 33m
Sat 9/197:46 pm -
1 stop14h 34m
Deal found 8/3![Frontier logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:26 am -
1 stop7h 35m
Mon 9/217:46 pm -
2 stops19h 31m
Deal found 8/2![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:20 am -
2 stops11h 41m
Sun 9/207:46 pm -
1 stop14h 34m
Deal found 8/2![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:28 pm -
1 stop22h 33m
Sat 10/37:46 pm -
1 stop14h 34m
Deal found 8/3![Frontier logo]()
$204
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 August 4, 2026.
Search for one-way flight options from Chicago to Jacksonville. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
This American Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:05 pm -
Nonstop2h 35m
Deal found 8/3![American Airlines logo]()
$99
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:45 pm -
Nonstop2h 20m
Deal found 7/30![Southwest logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:11 am -
1 stop24h 14m
Deal found 7/31![Multiple Airlines logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:26 am -
1 stop7h 35m
Deal found 8/1![Frontier logo]()
$101
This Trip.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:05 am -
1 stop10h 05m
Deal found 8/2![Frontier logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/251:59 pm -
1 stop27h 11m
Deal found 8/3![Frontier logo]()
$104
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:40 am -
1 stop10h 11m
Deal found 7/30![Frontier logo]()
$105
This Trip.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:05 am -
1 stop10h 05m
Deal found 8/3![Frontier logo]()
$108
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:27 am -
1 stop3h 53m
Deal found 8/3![Delta logo]()
$109
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:45 pm -
1 stop7h 05m
Deal found 7/31![Southwest logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:05 am -
1 stop6h 59m
Deal found 8/4![Multiple Airlines logo]()
$110
This Super.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2511:50 am -
1 stop5h 20m
Deal found 8/3![Frontier logo]()
$112
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 August 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $203 (Kiwi.com) |
One-way from | $99 (American Airlines) |
Popular in | December |
Cheapest in | August |
Average price | $295 |
Good round-trip deal | $295 or less |
Good one-way deal | $187 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 2,558,603 searches. Data last updated August 4, 2026.
Use the filters below to find and compare flights from Chicago to Jacksonville that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoJacksonville
MDW - JAX
MDWJAX
Chicago Midway
Thu 10/22
3:00 pm-6:15 pm
Nonstop2h 15m
Jacksonville
Mon 11/2
5:20 pm-12:05 am
2 stops7h 45m
$212
ChicagoJacksonville
ORD - JAX
ORDJAX
Chicago O'Hare Intl
Sat 9/5
6:40 am-1:36 pm
1 stop5h 56m
Jacksonville
Sat 9/12
1:02 pm-4:37 pm
1 stop4h 35m
$217
ChicagoJacksonville
MDW - JAX
MDWJAX
Chicago Midway
Mon 8/24
9:20 am-5:05 pm
1 stop6h 45m
Jacksonville
Thu 8/27
4:30 pm-11:20 pm
2 stops7h 50m
$222
ChicagoJacksonville
ORD - JAX
ORDJAX
Chicago O'Hare Intl
Sat 9/5
7:00 am-2:40 pm
1 stop6h 40m
Jacksonville
Sun 9/6
7:10 am-1:49 pm
1 stop7h 39m
$255
ChicagoJacksonville
ORD - JAX
ORDJAX
Chicago O'Hare Intl
Tue 9/15
3:00 pm-10:29 pm
1 stop6h 29m
Jacksonville
Sun 9/20
7:19 am-1:45 pm
1 stop7h 26m
$268
ChicagoJacksonville
ORD - JAX
ORDJAX
Chicago O'Hare Intl
Fri 8/21
12:56 pm-8:54 pm
1 stop6h 58m
Jacksonville
Mon 8/24
7:30 am-9:18 am
Nonstop2h 48m
$288
Quickest round-trip
ChicagoJacksonville
ORD - JAX
ORDJAX
Chicago O'Hare Intl
Mon 9/28
3:35 pm-7:09 pm
Nonstop2h 34m
Jacksonville
Thu 10/1
9:40 am-11:26 am
Nonstop2h 46m
$305
ChicagoJacksonville
ORD - JAX
ORDJAX
Chicago O'Hare Intl
Wed 8/26
10:29 am-2:04 pm
Nonstop2h 35m
Jacksonville
Sat 8/29
12:37 pm-2:30 pm
Nonstop2h 53m
$305
ChicagoJacksonville
ORD - JAX
ORDJAX
Chicago O'Hare Intl
Sat 9/12
10:30 am-2:05 pm
Nonstop2h 35m
Jacksonville
Sat 9/19
4:45 pm-6:34 pm
Nonstop2h 49m
$305
ChicagoJacksonville
MDW - JAX
MDWJAX
Chicago Midway
Wed 9/16
6:30 am-2:55 pm
1 stop7h 25m
Jacksonville
Wed 9/23
5:25 pm-6:50 pm
Nonstop2h 25m
$315
Showing 1-10 of 37 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 August.
| 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 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
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
What is the cheapest month to book a flight from Chicago to Jacksonville?
Currently, September is the cheapest month in which you can book a flight from Chicago to Jacksonville (average of $303). Flying from Chicago to Jacksonville in December is currently the most expensive (average of $417). 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 August 4, 2026.
It’s typically best to fly out from Chicago to Jacksonville at noon. Doing so could potentially save you 12% 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 August 4, 2026.
The most flights from CHI to JAX are scheduled on a Monday (27 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (11 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 $243 and $379 in September.The cheapest round-trip price found within the last 5 days was $203 on Frontier (Sep 13-Sep 19).
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 55 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 August 1, 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. Monday afternoons 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 August 4, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines 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.
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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
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
Complete your trip
Flights by cabin class
Jacksonville flight routes
Other flight options
Other flights from Chicago
Popular flights
Alternative routes for Chicago to Jacksonville
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Jacksonville by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Jacksonville by cabin class
Find flights from Chicago to Jacksonville, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 August 4, 2026.
Chicago and Jacksonville flights
Browse other Chicago and Jacksonville flight options. Last updated on August 4, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 2,558,603 searches. Data last updated August 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$83 | Average$337 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$128 | Average$255 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$186 | Average$350 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$225 | Average$375 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$236 | Average$349 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$246 | Average$378 | FlexibilityNo cancel fee | On-time69% |