$87+ Cheap flights from Jacksonville (JAX) to Chicago (CHI)
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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — CHI
Sep 3 — Sep 101
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 September or January, booked 82 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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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 August 4, 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 August 4, 2026.
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.
Wed 12/166:40 pm -
1 stop5h 35m
Sat 1/97:30 am -
Nonstop2h 41m
Deal found 7/30![United Airlines logo]()
$197
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.
Sat 9/57:30 am -
Nonstop2h 20m
Sun 9/61:40 pm -
Nonstop2h 15m
Deal found 8/3![Southwest logo]()
$197
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.
Wed 8/269:38 pm -
1 stop16h 12m
Sat 8/291:59 pm -
1 stop27h 11m
Deal found 7/31![Multiple Airlines logo]()
$198
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:14 pm -
Nonstop2h 54m
Sun 9/69:40 am -
Nonstop2h 36m
Deal found 8/1![American Airlines logo]()
$199
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:46 pm -
1 stop17h 05m
Mon 9/286:20 am -
2 stops11h 41m
Deal found 7/30![Frontier logo]()
$200
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.
Wed 9/167:46 pm -
1 stop14h 34m
Wed 9/237:28 pm -
1 stop22h 33m
Deal found 8/2![Frontier logo]()
$201
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.
Wed 8/197:05 pm -
1 stop13h 48m
Mon 8/247:05 am -
1 stop10h 05m
Deal found 7/31![Frontier logo]()
$202
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:46 pm -
1 stop4h 58m
Mon 9/216:25 am -
1 stop11h 36m
Deal found 7/30![Frontier logo]()
$202
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:05 pm -
2 stops18h 45m
Mon 8/317:05 am -
1 stop10h 05m
Deal found 7/30![Frontier logo]()
$203
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.
Fri 9/47:05 pm -
1 stop13h 48m
Tue 9/87:05 am -
1 stop10h 05m
Deal found 7/31![Frontier logo]()
$204
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 8/317:05 pm -
1 stop13h 48m
Thu 9/106:20 am -
2 stops11h 41m
Deal found 8/2![Frontier logo]()
$205
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.
Fri 10/27:46 pm -
1 stop17h 05m
Mon 10/510:26 am -
1 stop7h 35m
Deal found 8/2![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 August 4, 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 August 4, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/301:30 pm -
Nonstop2h 20m
Mon 11/212:50 pm -
Nonstop2h 15m
Deal found 8/4![Southwest logo]()
$251
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 9/57:30 am -
Nonstop2h 48m
Mon 9/73:50 pm -
Nonstop2h 35m
Deal found 7/31![United Airlines logo]()
$262
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:08 pm -
1 stop5h 51m
Thu 11/266:45 am -
1 stop5h 39m
Deal found 8/4![Delta logo]()
$294
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 9/117:00 am -
Nonstop2h 25m
Mon 9/147:30 am -
1 stop4h 55m
Deal found 7/31![Southwest logo]()
$261
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:59 pm -
1 stop6h 50m
Sun 9/66:40 am -
1 stop4h 04m
Deal found 8/2![Delta logo]()
$302
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.
Thu 9/176:40 am -
Nonstop2h 49m
Mon 9/217:40 pm -
Nonstop2h 40m
Deal found 8/4![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.
Fri 8/287:00 am -
Nonstop2h 25m
Mon 8/316:45 pm -
Nonstop2h 15m
Deal found 7/30![Southwest logo]()
$282
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 8/2612:37 pm -
Nonstop2h 53m
Thu 8/2712:56 pm -
1 stop6h 58m
Deal found 8/3![United Airlines logo]()
$311
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 9/141:00 pm -
2 stops7h 30m
Mon 9/217:30 am -
1 stop4h 55m
Deal found 7/30![Southwest logo]()
$299
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.
Fri 9/117:10 pm -
1 stop5h 30m
Sun 9/137:05 am -
Nonstop2h 46m
Deal found 8/4![United Airlines logo]()
$322
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.
Wed 8/265:25 pm -
Nonstop2h 25m
Thu 8/276:45 pm -
Nonstop2h 15m
Deal found 8/3![Southwest logo]()
$305
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.
Wed 9/167:15 am -
Nonstop2h 48m
Fri 9/187:40 pm -
Nonstop2h 40m
Deal found 8/4![United Airlines logo]()
$328
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.
Thu 10/151:30 pm -
Nonstop2h 20m
Mon 10/196:30 pm -
1 stop3h 50m
Deal found 8/2![Southwest logo]()
$315
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 9/57:30 am -
Nonstop2h 48m
Wed 9/97:05 am -
Nonstop2h 46m
Deal found 8/4![United Airlines logo]()
$331
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 9/117:00 am -
Nonstop2h 25m
Sun 9/131:40 pm -
Nonstop2h 15m
Deal found 7/31![Southwest logo]()
$322
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.
Tue 10/69:40 am -
Nonstop2h 46m
Fri 10/910:25 am -
Nonstop2h 35m
Deal found 7/31![United Airlines logo]()
$336
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.
Sat 9/57:30 am -
Nonstop2h 20m
Mon 9/77:55 am -
1 stop8h 10m
Deal found 8/3![Southwest logo]()
$328
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.
Fri 9/114:45 pm -
Nonstop2h 49m
Sat 9/1212:55 pm -
1 stop6h 59m
Deal found 8/4![United Airlines logo]()
$337
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 9/87:36 am -
Nonstop2h 48m
Fri 9/1112:55 pm -
1 stop6h 59m
Deal found 8/3![United Airlines logo]()
$337
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/43:50 pm -
1 stop6h 10m
Tue 9/85:55 pm -
Nonstop2h 25m
Deal found 8/1![Southwest logo]()
$338
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.
Thu 10/89:40 am -
Nonstop2h 46m
Mon 10/123:35 pm -
Nonstop2h 34m
Deal found 8/4![United Airlines logo]()
$364
Last-minute flights from Jacksonville to ChicagoDiscover last-minute flight deals from Jacksonville to Chicago. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from Jacksonville to Chicago. Data last updated August 4, 2026 and is based on user searches.
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.
Wed 8/197:05 pm -
1 stop13h 48m
Mon 8/247:05 am -
1 stop10h 05m
Deal found 7/31![Frontier logo]()
$202
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.
Wed 8/269:38 pm -
1 stop16h 12m
Sat 8/291:59 pm -
1 stop27h 11m
Deal found 7/31![Multiple Airlines logo]()
$198
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:05 pm -
2 stops18h 45m
Mon 8/317:05 am -
1 stop10h 05m
Deal found 7/30![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.
Sun 8/307:05 pm -
1 stop13h 48m
Thu 9/1010:26 am -
1 stop7h 35m
Deal found 8/2![Frontier logo]()
$208
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 8/317:05 pm -
1 stop13h 48m
Thu 9/106:20 am -
2 stops11h 41m
Deal found 8/2![Frontier logo]()
$205
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.
Fri 9/47:05 pm -
1 stop13h 48m
Tue 9/87:05 am -
1 stop10h 05m
Deal found 7/31![Frontier logo]()
$204
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.
Sat 9/57:30 am -
Nonstop2h 48m
Sat 9/127:49 pm -
Nonstop2h 40m
Deal found 7/30![United Airlines logo]()
$197
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.
Sat 9/57:30 am -
Nonstop2h 20m
Sun 9/61:40 pm -
Nonstop2h 15m
Deal found 8/3![Southwest logo]()
$197
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:14 pm -
Nonstop2h 54m
Sun 9/69:40 am -
Nonstop2h 36m
Deal found 8/1![American Airlines logo]()
$199
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:46 pm -
1 stop4h 58m
Mon 9/216:25 am -
1 stop11h 36m
Deal found 7/30![Frontier logo]()
$202
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.
Wed 9/167:46 pm -
1 stop14h 34m
Wed 9/237:28 pm -
1 stop22h 33m
Deal found 8/2![Frontier logo]()
$201
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:46 pm -
1 stop17h 05m
Mon 9/286:20 am -
2 stops11h 41m
Deal found 7/30![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 August 4, 2026.
Search for one-way flight options from Jacksonville to Chicago. Find affordable one-way fares based on user searches. Data last updated 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.
Mon 8/247:05 pm -
1 stop25h 54m
Deal found 8/3![Frontier logo]()
$87
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.
Tue 8/258:44 pm -
1 stop17h 06m
Deal found 7/31![Multiple Airlines logo]()
$88
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:05 pm -
1 stop4h 42m
Deal found 7/30![Frontier logo]()
$88
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.
Thu 8/207:05 pm -
1 stop4h 42m
Deal found 7/30![Frontier logo]()
$89
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.
Mon 8/317:05 pm -
1 stop13h 48m
Deal found 7/31![Frontier logo]()
$90
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.
Mon 10/57:46 pm -
1 stop17h 05m
Deal found 7/31![Frontier logo]()
$93
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 9/287:46 pm -
1 stop17h 05m
Deal found 8/2![Frontier logo]()
$95
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.
Mon 11/26:46 pm -
1 stop18h 16m
Deal found 8/1![Frontier logo]()
$96
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.
Mon 9/283:41 pm -
1 stop24h 39m
Deal found 8/4![Multiple Airlines logo]()
$98
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 9/54:45 pm -
Nonstop2h 49m
Deal found 7/31![United 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 8/277:00 am -
Nonstop2h 25m
Deal found 7/30![Southwest logo]()
$99
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:05 pm -
1 stop26h 03m
Deal found 8/1![Frontier logo]()
$100
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 August 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $197 (United Airlines) |
One-way from | $87 (Kiwi.com) |
Popular in | May |
Cheapest in | September |
Average price | $325 |
Good round-trip deal | $317 or less |
Good one-way deal | $218 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 2,558,603 searches. Data last updated August 4, 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
Quickest round-trip
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Fri 10/30
1:30 pm-2:50 pm
Nonstop2h 20m
Chicago Midway
Mon 11/2
12:50 pm-4:05 pm
Nonstop2h 15m
$251
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Fri 9/11
7:00 am-8:25 am
Nonstop2h 25m
Chicago Midway
Mon 9/14
7:30 am-1:25 pm
1 stop4h 55m
$261
JacksonvilleChicago
JAX - ORD
JAXORD
Jacksonville
Sat 9/5
7:30 am-9:18 am
Nonstop2h 48m
Chicago O'Hare Intl
Mon 9/7
3:50 pm-7:25 pm
Nonstop2h 35m
$262
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Fri 8/28
7:00 am-8:25 am
Nonstop2h 25m
Chicago Midway
Mon 8/31
6:45 pm-10:00 pm
Nonstop2h 15m
$282
JacksonvilleChicago
JAX - ORD
JAXORD
Jacksonville
Fri 11/20
7:08 pm-11:59 pm
1 stop5h 51m
Chicago O'Hare Intl
Thu 11/26
6:45 am-1:24 pm
1 stop5h 39m
$294
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Mon 9/14
1:00 pm-7:30 pm
2 stops7h 30m
Chicago Midway
Mon 9/21
7:30 am-1:25 pm
1 stop4h 55m
$299
JacksonvilleChicago
JAX - ORD
JAXORD
Jacksonville
Fri 8/28
12:59 pm-6:49 pm
1 stop6h 50m
Chicago O'Hare Intl
Sun 9/6
6:40 am-11:44 am
1 stop4h 04m
$302
JacksonvilleChicago
JAX - ORD
JAXORD
Jacksonville
Thu 9/17
6:40 am-8:29 am
Nonstop2h 49m
Chicago O'Hare Intl
Mon 9/21
7:40 pm-11:20 pm
Nonstop2h 40m
$305
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Wed 8/26
5:25 pm-6:50 pm
Nonstop2h 25m
Chicago Midway
Thu 8/27
6:45 pm-10:00 pm
Nonstop2h 15m
$305
JacksonvilleChicago
JAX - ORD
JAXORD
Jacksonville
Wed 8/26
12:37 pm-2:30 pm
Nonstop2h 53m
Chicago O'Hare Intl
Thu 8/27
12:56 pm-8:54 pm
1 stop6h 58m
$311
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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | 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, September is the cheapest month in which you can book a flight from Jacksonville to Chicago (average of $294). Flying from Jacksonville to Chicago in March is currently the most expensive (average of $382). 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 August 4, 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 22% 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 August 4, 2026.
The most flights from JAX to CHI are scheduled on a Monday (27 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (13 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 $283 and $379 in September.The cheapest round-trip price found within the last 5 days was $197 on United Airlines (Sep 5-Sep 12).
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 79 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 August 1, 2026.
Travelers seeking maximum savings on their Jacksonville to Chicago flight should consider departing on Saturday at noon 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 August 4, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines 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
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Food
7.0
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
Saint Joseph
Porter
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Other flights to Chicago
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Jacksonville and Chicago flights
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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 August 4, 2026.
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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 2,558,603 searches. Data last updated August 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$121 | Average$291 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$134 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$197 | Average$357 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$197 | Average$358 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$206 | Average$301 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$254 | Average$379 | FlexibilityNo cancel fee | On-time69% |