$121+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — CHI
May 29 — Jun 51
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 August, booked 71 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
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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 April 29, 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 April 29, 2026.
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/236:50 am
JAX
- ORD
Nonstop2h 49m
American Airlines
Tue 5/267:25 pm
ORD
- JAX
Nonstop2h 33m
American Airlines
Deal found 4/28![American Airlines logo]()
$242
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 6/610:55 am
JAX
- MDW
Nonstop2h 25m
Southwest
Tue 6/96:20 pm
MDW
- JAX
Nonstop2h 20m
Southwest
Deal found 4/25![Southwest logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 6/46:30 pm
JAX
- ORD
2 stops19h 07m
Frontier
Sun 6/76:55 am
ORD
- JAX
1 stop9h 40m
Frontier
Deal found 4/26![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 6/96:28 pm
JAX
- MDW
1 stop4h 43m
Frontier
Tue 6/1612:27 pm
MDW
- JAX
2 stops25h 37m
Frontier
Deal found 4/25![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/66:30 pm
JAX
- ORD
1 stop14h 25m
Frontier
Thu 6/186:55 am
ORD
- JAX
1 stop9h 38m
Frontier
Deal found 4/27![Frontier logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/196:28 pm
JAX
- MDW
1 stop17h 36m
Frontier
Sun 6/216:00 am
MDW
- JAX
1 stop10h 33m
Frontier
Deal found 4/28![Frontier logo]()
$245
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Fri 5/13:27 pm
JAX
- ORD
1 stop5h 36m
Frontier
Fri 5/86:55 am
ORD
- JAX
1 stop9h 40m
Frontier
Deal found 4/28![Frontier logo]()
$246
This Expedia deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Fri 6/56:30 pm
JAX
- MDW
1 stop4h 32m
Frontier
Sun 6/76:00 am
MDW
- JAX
1 stop10h 35m
Frontier
Deal found 4/28![Frontier logo]()
$246
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Tue 5/266:20 am
JAX
- ORD
1 stop6h 58m
American Airlines
Tue 6/27:30 pm
ORD
- JAX
Nonstop2h 33m
American Airlines
Deal found 4/28![American Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/277:20 am
JAX
- MDW
Nonstop2h 30m
Southwest
Wed 6/310:25 am
MDW
- JAX
1 stop7h 10m
Southwest
Deal found 4/26![Southwest logo]()
$247
This American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 6/67:57 pm
JAX
- ORD
1 stop5h 01m
American Airlines
Tue 6/97:22 pm
ORD
- JAX
Nonstop2h 28m
American Airlines
Deal found 4/25![American Airlines logo]()
$248
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 6/31:50 pm
JAX
- MDW
1 stop7h 30m
Southwest
Sat 6/67:50 am
MDW
- JAX
Nonstop2h 25m
Southwest
Deal found 4/26![Southwest logo]()
$248
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 April 29, 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 April 29, 2026.
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 6/610:55 am
JAX
- MDW
Nonstop2h 25m
Southwest
Tue 6/93:10 pm
MDW
- JAX
1 stop4h 55m
Southwest
Deal found 4/25![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Mon 5/183:48 pm
JAX
- ORD
1 stop5h 38m
Delta
Wed 5/209:49 am
ORD
- JAX
1 stop5h 44m
Delta
Deal found 4/26![Delta logo]()
$262
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/297:20 am
JAX
- ORD
Nonstop2h 52m
United Airlines
Tue 6/26:19 pm
ORD
- JAX
Nonstop2h 40m
United Airlines
Deal found 4/27![United Airlines logo]()
$280
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/234:47 pm
JAX
- ORD
Nonstop2h 53m
United Airlines
Mon 5/256:35 am
ORD
- JAX
Nonstop2h 44m
United Airlines
Deal found 4/29![United Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Thu 8/68:18 pm
JAX
- ORD
1 stop4h 35m
Delta
Tue 8/117:00 am
ORD
- JAX
1 stop6h 41m
Delta
Deal found 4/25![Delta logo]()
$300
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/236:45 pm
JAX
- MDW
Nonstop2h 25m
Southwest
Sun 6/288:05 am
MDW
- JAX
1 stop4h 10m
Southwest
Deal found 4/28![Southwest logo]()
$301
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Tue 9/81:20 pm
JAX
- ORD
1 stop6h 19m
Delta
Thu 9/106:00 am
ORD
- JAX
1 stop7h 41m
Delta
Deal found 4/27![Delta logo]()
$300
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/187:15 pm
JAX
- MDW
Nonstop2h 30m
Southwest
Tue 6/236:20 pm
MDW
- JAX
Nonstop2h 20m
Southwest
Deal found 4/28![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/27:20 am
JAX
- ORD
Nonstop2h 52m
United Airlines
Wed 6/310:42 am
ORD
- JAX
Nonstop2h 45m
United Airlines
Deal found 4/24![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Thu 6/258:18 pm
JAX
- ORD
1 stop4h 41m
Delta
Wed 7/16:35 am
ORD
- JAX
1 stop6h 08m
Delta
Deal found 4/28![Delta logo]()
$300
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/106:45 am
JAX
- MDW
2 stops7h 50m
Southwest
Fri 6/121:00 pm
MDW
- JAX
2 stops6h 10m
Southwest
Deal found 4/27![Southwest logo]()
$310
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:50 pm
JAX
- ORD
1 stop6h 51m
Delta
Sun 5/3111:26 am
ORD
- JAX
1 stop4h 07m
Delta
Deal found 4/24![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/306:10 am
JAX
- MDW
2 stops12h 00m
Southwest
Tue 6/210:10 am
MDW
- JAX
2 stops6h 10m
Southwest
Deal found 4/28![Southwest logo]()
$316
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/242:48 pm
JAX
- ORD
1 stop4h 54m
Delta
Sun 6/286:30 am
ORD
- JAX
1 stop6h 38m
Delta
Deal found 4/27![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/176:45 pm
JAX
- MDW
Nonstop2h 25m
Southwest
Sat 6/207:50 am
MDW
- JAX
Nonstop2h 25m
Southwest
Deal found 4/27![Southwest logo]()
$316
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Tue 5/125:05 am
JAX
- ORD
1 stop6h 11m
Delta
Tue 5/195:30 am
ORD
- JAX
1 stop5h 15m
Delta
Deal found 4/25![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/187:50 am
JAX
- MDW
Nonstop2h 30m
Southwest
Wed 5/204:50 pm
MDW
- JAX
1 stop3h 40m
Southwest
Deal found 4/26![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/255:00 pm
JAX
- MDW
1 stop6h 20m
Southwest
Mon 6/16:50 pm
MDW
- JAX
Nonstop2h 15m
Southwest
Deal found 4/27![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/318:18 pm
JAX
- ORD
1 stop4h 41m
Delta
Mon 6/18:10 am
ORD
- JAX
1 stop4h 25m
Delta
Deal found 4/28![Delta logo]()
$356
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/242:55 pm
JAX
- MDW
2 stops8h 05m
Southwest
Sat 6/278:00 am
MDW
- JAX
2 stops8h 40m
Southwest
Deal found 4/28![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/187:15 pm
JAX
- MDW
Nonstop2h 30m
Southwest
Sun 6/216:50 pm
MDW
- JAX
Nonstop2h 15m
Southwest
Deal found 4/27![Southwest logo]()
$385
Last-minute flights from Jacksonville to ChicagoDiscover last-minute flight deals from Jacksonville to Chicago. Data last updated April 29, 2026 and is based on user searches.
Discover last-minute flight deals from Jacksonville to Chicago. Data last updated April 29, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Fri 5/13:27 pm
JAX
- ORD
1 stop5h 36m
Frontier
Fri 5/86:55 am
ORD
- JAX
1 stop9h 40m
Frontier
Deal found 4/28![Frontier logo]()
$246
This Expedia deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Fri 5/156:30 pm
JAX
- MDW
1 stop4h 32m
Frontier
Sun 5/176:00 am
MDW
- JAX
1 stop10h 35m
Frontier
Deal found 4/28![Frontier logo]()
$256
This Expedia deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Mon 5/186:30 pm
JAX
- MDW
1 stop4h 32m
Frontier
Sat 5/236:00 am
MDW
- JAX
1 stop10h 35m
Frontier
Deal found 4/27![Frontier logo]()
$250
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/236:50 am
JAX
- ORD
Nonstop2h 49m
American Airlines
Tue 5/267:25 pm
ORD
- JAX
Nonstop2h 33m
American Airlines
Deal found 4/28![American Airlines logo]()
$242
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/236:42 pm
JAX
- ORD
Nonstop2h 58m
United Airlines
Wed 6/31:18 pm
ORD
- JAX
1 stop5h 50m
United Airlines
Deal found 4/24![United Airlines logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/239:45 pm
JAX
- ORD
2 stops33h 39m
Frontier
Sat 6/61:50 pm
ORD
- JAX
1 stop26h 45m
Frontier
Deal found 4/28![Frontier logo]()
$251
This Booking.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2411:28 am
JAX
- ORD
1 stop12h 18m
Frontier
Sun 5/316:55 am
ORD
- JAX
1 stop9h 40m
Frontier
Deal found 4/24![Frontier logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/258:36 pm
JAX
- ORD
2 stops40h 47m
Multiple Airlines
Mon 6/11:50 pm
ORD
- JAX
1 stop26h 45m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$257
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Tue 5/266:20 am
JAX
- ORD
1 stop6h 58m
American Airlines
Tue 6/27:30 pm
ORD
- JAX
Nonstop2h 33m
American Airlines
Deal found 4/28![American Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/277:20 am
JAX
- MDW
Nonstop2h 30m
Southwest
Wed 5/2710:25 am
MDW
- JAX
1 stop7h 10m
Southwest
Deal found 4/25![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/296:30 pm
JAX
- ORD
1 stop14h 25m
Frontier
Wed 6/34:05 pm
ORD
- JAX
2 stops24h 30m
Frontier
Deal found 4/28![Frontier logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/299:34 pm
JAX
- ORD
2 stops23h 07m
Multiple Airlines
Mon 6/86:55 am
ORD
- JAX
1 stop9h 40m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$259
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 April 29, 2026.
Search for one-way flight options from Jacksonville to Chicago. Find affordable one-way fares based on user searches. Data last updated April 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 7/16:28 pm
JAX
- ORD
1 stop26h 25m
Frontier
Deal found 4/29![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/19:27 pm
JAX
- MDW
2 stops25h 35m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 8/56:28 pm
JAX
- ORD
1 stop22h 53m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/46:28 pm
JAX
- ORD
1 stop14h 25m
Frontier
Deal found 4/27![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/189:45 pm
JAX
- ORD
2 stops23h 06m
Frontier
Deal found 4/27![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/256:28 pm
JAX
- ORD
1 stop14h 35m
Frontier
Deal found 4/24![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 7/166:28 pm
JAX
- MDW
1 stop28h 40m
Frontier
Deal found 4/24![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/136:28 pm
JAX
- ORD
1 stop14h 35m
Frontier
Deal found 4/24![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/229:38 pm
JAX
- ORD
1 stop12h 44m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/269:03 pm
JAX
- MDW
2 stops25h 59m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/249:45 pm
JAX
- ORD
2 stops35h 10m
Frontier
Deal found 4/28![Frontier logo]()
$134
This Super.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/23:08 pm
JAX
- MDW
1 stop4h 29m
Frontier
Deal found 4/26![Frontier logo]()
$134
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 April 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $242 (American Airlines) |
One-way from | $121 (Kiwi.com) |
Popular in | April |
Cheapest in | September |
Average price | $387 |
Good round-trip deal | $367 or less |
Good one-way deal | $175 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 April 29, 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 - MDW
JAXMDW
Jacksonville
Sat 6/6
10:55 am-12:20 pm
Nonstop2h 25m
Chicago Midway
Tue 6/9
3:10 pm-9:05 pm
1 stop4h 55m
$252
JacksonvilleChicago
JAX - ORD
JAXORD
Jacksonville
Mon 5/18
3:48 pm-8:26 pm
1 stop5h 38m
Chicago O'Hare Intl
Wed 5/20
9:49 am-4:33 pm
1 stop5h 44m
$262
JacksonvilleChicago
JAX - ORD
JAXORD
Jacksonville
Fri 5/29
7:20 am-9:12 am
Nonstop2h 52m
Chicago O'Hare Intl
Tue 6/2
6:19 pm-9:59 pm
Nonstop2h 40m
$280
JacksonvilleChicago
JAX - ORD
JAXORD
Jacksonville
Sat 5/23
4:47 pm-6:40 pm
Nonstop2h 53m
Chicago O'Hare Intl
Mon 5/25
6:35 am-10:19 am
Nonstop2h 44m
$287
JacksonvilleChicago
JAX - ORD
JAXORD
Jacksonville
Thu 8/6
8:18 pm-11:53 pm
1 stop4h 35m
Chicago O'Hare Intl
Tue 8/11
7:00 am-2:41 pm
1 stop6h 41m
$300
JacksonvilleChicago
JAX - ORD
JAXORD
Jacksonville
Tue 9/8
1:20 pm-6:39 pm
1 stop6h 19m
Chicago O'Hare Intl
Thu 9/10
6:00 am-2:41 pm
1 stop7h 41m
$300
JacksonvilleChicago
JAX - ORD
JAXORD
Jacksonville
Thu 6/25
8:18 pm-11:59 pm
1 stop4h 41m
Chicago O'Hare Intl
Wed 7/1
6:35 am-1:43 pm
1 stop6h 08m
$300
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Tue 6/23
6:45 pm-8:10 pm
Nonstop2h 25m
Chicago Midway
Sun 6/28
8:05 am-1:15 pm
1 stop4h 10m
$301
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Thu 6/18
7:15 pm-8:45 pm
Nonstop2h 30m
Chicago Midway
Tue 6/23
6:20 pm-9:40 pm
Nonstop2h 20m
$307
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Wed 6/10
6:45 am-1:35 pm
2 stops7h 50m
Chicago Midway
Fri 6/12
1:00 pm-8:10 pm
2 stops6h 10m
$310
Showing 1-10 of 42 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 April.
| 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-ORD
JAX-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Jacksonville to Chicago
JAX-CHI
JAX-ORD
JAX-MDW
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 70 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 $78). Flying from Jacksonville to Chicago in February is currently the most expensive (average of $177). 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 April 29, 2026.
One of the essential ways to save on airfare from Jacksonville to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 17% on airfare.
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 April 25, 2026.
Travelers seeking maximum savings on their Jacksonville to Chicago flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 April 29, 2026.
The most flights from JAX to CHI are scheduled on a Monday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 on average).
How much does it cost to fly round-trip from Jacksonville to Chicago?
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 April 29, 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.
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
Hammond
Porter
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Other flights to Chicago
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Complete your trip
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Jacksonville and Chicago flights
Browse other Jacksonville and Chicago flight options. Last updated on April 29, 2026.
Other flights from Jacksonville
Browse through other flights departing from Jacksonville. Flights are based on user searches made on Cheapflights and were last updated on April 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Jacksonville to Chicago
Discover the top 5 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 April 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$121 | Average$246 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$136 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$179 | Average$334 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$202 | Average$345 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$230 | Average$370 | FlexibilityNo cancel fee | On-time69% |