$152+ Cheap flights from Jackson, MS (JAN) 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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
May 24 — May 311
Round-trip
1 adult, Economy
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1. Tell us where you want to go
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Cheapest flights from Jackson to ChicagoExplore the most affordable flight options available from Jackson to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2026.
Explore the most affordable flight options available from Jackson to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2026.
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/205:00 pm
JAN
- ORD
1 stop4h 53m
Delta
Tue 5/265:30 am
ORD
- JAN
1 stop6h 42m
Delta
Deal found 4/20![Delta logo]()
$251
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/205:00 pm
JAN
- ORD
1 stop4h 53m
Delta
Wed 5/275:30 am
ORD
- JAN
1 stop6h 42m
Delta
Deal found 4/22![Delta logo]()
$257
This American Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:29 pm
JAN
- ORD
1 stop5h 10m
American Airlines
Tue 6/95:00 am
ORD
- JAN
1 stop6h 54m
American Airlines
Deal found 4/21![American Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:00 pm
JAN
- MDW
1 stop4h 09m
Delta
Tue 6/96:05 am
MDW
- JAN
1 stop3h 58m
Delta
Deal found 4/21![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/205:00 pm
JAN
- ORD
1 stop6h 59m
Delta
Sat 5/2312:00 pm
ORD
- JAN
1 stop6h 52m
Delta
Deal found 4/21![Delta logo]()
$283
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/612:15 pm
JAN
- MDW
1 stop4h 45m
Southwest
Tue 6/911:25 am
MDW
- JAN
2 stops7h 20m
Southwest
Deal found 4/21![Southwest logo]()
$283
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/187:23 pm
JAN
- ORD
1 stop4h 36m
Delta
Wed 5/205:30 am
ORD
- JAN
1 stop7h 13m
Delta
Deal found 4/23![Delta logo]()
$290
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/182:55 pm
JAN
- MDW
1 stop6h 14m
Delta
Wed 5/206:23 am
MDW
- JAN
1 stop6h 20m
Delta
Deal found 4/23![Delta logo]()
$290
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:55 pm
JAN
- ORD
1 stop5h 31m
Delta
Fri 6/56:06 pm
ORD
- JAN
1 stop5h 12m
Delta
Deal found 4/22![Delta logo]()
$302
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:40 pm
JAN
- ORD
1 stop5h 37m
Delta
Sat 8/221:15 pm
ORD
- JAN
1 stop5h 34m
Delta
Deal found 4/20![Delta logo]()
$303
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:35 pm
JAN
- MDW
1 stop4h 11m
Delta
Sat 8/2210:35 am
MDW
- JAN
1 stop5h 18m
Delta
Deal found 4/20![Delta logo]()
$303
This American Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/85:45 am
JAN
- ORD
1 stop7h 46m
American Airlines
Tue 8/115:00 am
ORD
- JAN
1 stop6h 50m
American Airlines
Deal found 4/22![American Airlines logo]()
$319
Best flights from Jackson to ChicagoDiscover carefully curated flight deals from Jackson to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 24, 2026.
Discover carefully curated flight deals from Jackson to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 24, 2026.
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 8/206:59 pm
JAN
- ORD
1 stop4h 58m
Delta
Sat 8/225:55 pm
ORD
- JAN
1 stop5h 24m
Delta
Deal found 4/23![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/191:00 pm
JAN
- MDW
2 stops8h 50m
Southwest
Tue 5/2611:35 am
MDW
- JAN
2 stops8h 45m
Southwest
Deal found 4/19![Southwest logo]()
$372
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 8/119:00 am
JAN
- ORD
2 stops13h 41m
United Airlines
Wed 8/125:30 am
ORD
- JAN
1 stop13h 58m
United Airlines
Deal found 4/23![United Airlines logo]()
$514
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/302:55 pm
JAN
- ORD
1 stop6h 58m
Delta
Mon 6/15:30 am
ORD
- JAN
1 stop4h 34m
Delta
Deal found 4/21![Delta logo]()
$303
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 8/202:40 pm
JAN
- MDW
1 stop7h 06m
Delta
Sat 8/2210:35 am
MDW
- JAN
1 stop5h 18m
Delta
Deal found 4/23![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/77:15 pm
JAN
- MDW
1 stop4h 35m
Southwest
Sat 7/115:05 am
MDW
- JAN
1 stop6h 35m
Southwest
Deal found 4/21![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/185:00 pm
JAN
- ORD
1 stop4h 53m
Delta
Mon 5/255:30 am
ORD
- JAN
1 stop4h 34m
Delta
Deal found 4/20![Delta logo]()
$352
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/125:10 am
JAN
- MDW
1 stop10h 45m
Southwest
Mon 6/155:00 am
MDW
- JAN
1 stop5h 45m
Southwest
Deal found 4/21![Southwest logo]()
$392
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:10 am
JAN
- MDW
2 stops10h 45m
Southwest
Tue 7/143:10 pm
MDW
- JAN
1 stop3h 35m
Southwest
Deal found 4/21![Southwest logo]()
$392
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:10 pm
JAN
- ORD
1 stop4h 43m
Delta
Tue 7/148:03 am
ORD
- JAN
1 stop4h 02m
Delta
Deal found 4/21![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:45 pm
JAN
- MDW
2 stops9h 15m
Southwest
Mon 6/111:40 am
MDW
- JAN
2 stops7h 25m
Southwest
Deal found 4/21![Southwest logo]()
$401
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 10/152:40 pm
JAN
- MDW
1 stop7h 05m
Delta
Sun 10/186:00 am
MDW
- JAN
1 stop5h 22m
Delta
Deal found 4/23![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:00 pm
JAN
- MDW
2 stops8h 50m
Southwest
Mon 6/111:40 am
MDW
- JAN
2 stops7h 25m
Southwest
Deal found 4/22![Southwest logo]()
$417
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/512:54 pm
JAN
- ORD
1 stop7h 22m
Delta
Tue 5/126:06 pm
ORD
- JAN
1 stop5h 12m
Delta
Deal found 4/20![Delta logo]()
$402
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1112:15 pm
JAN
- MDW
1 stop8h 45m
Southwest
Sat 5/165:00 am
MDW
- JAN
1 stop6h 45m
Southwest
Deal found 4/19![Southwest logo]()
$417
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/55:36 am
JAN
- MDW
1 stop4h 20m
Delta
Tue 5/125:10 pm
MDW
- JAN
1 stop6h 08m
Delta
Deal found 4/19![Delta logo]()
$402
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:45 am
JAN
- ORD
2 stops13h 05m
Southwest
Mon 5/187:35 pm
ORD
- JAN
2 stops16h 45m
Southwest
Deal found 4/19![Southwest logo]()
$446
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 7/810:46 am
JAN
- ORD
1 stop5h 58m
Delta
Fri 7/101:44 pm
ORD
- JAN
1 stop6h 56m
Delta
Deal found 4/23![Delta logo]()
$433
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/61:00 pm
JAN
- ORD
2 stops8h 55m
Southwest
Sun 5/102:40 pm
ORD
- JAN
1 stop5h 00m
Southwest
Deal found 4/21![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:45 am
JAN
- ORD
2 stops9h 45m
Southwest
Sat 5/166:00 am
ORD
- JAN
2 stops11h 35m
Southwest
Deal found 4/20![Southwest logo]()
$499
Last-minute flights from Jackson to ChicagoDiscover last-minute flight deals from Jackson to Chicago. Data last updated April 24, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chicago. Data last updated April 24, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:05 pm
JAN
- ORD
1 stop5h 43m
American Airlines
Sat 5/166:41 pm
ORD
- JAN
1 stop5h 18m
American Airlines
Deal found 4/21![American Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/141:30 pm
JAN
- ORD
1 stop6h 56m
Delta
Thu 5/289:49 am
ORD
- JAN
1 stop4h 26m
Delta
Deal found 4/22![Delta logo]()
$337
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/187:23 pm
JAN
- ORD
1 stop4h 36m
Delta
Wed 5/205:30 am
ORD
- JAN
1 stop7h 13m
Delta
Deal found 4/23![Delta logo]()
$290
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/182:55 pm
JAN
- MDW
1 stop6h 14m
Delta
Wed 5/206:23 am
MDW
- JAN
1 stop6h 20m
Delta
Deal found 4/23![Delta logo]()
$290
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/191:00 pm
JAN
- MDW
1 stop3h 45m
Southwest
Tue 5/267:25 am
MDW
- JAN
1 stop4h 55m
Southwest
Deal found 4/19![Southwest logo]()
$320
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/205:00 pm
JAN
- ORD
1 stop4h 53m
Delta
Tue 5/265:30 am
ORD
- JAN
1 stop6h 42m
Delta
Deal found 4/20![Delta logo]()
$251
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/205:00 pm
JAN
- ORD
1 stop4h 53m
Delta
Wed 5/275:30 am
ORD
- JAN
1 stop6h 42m
Delta
Deal found 4/22![Delta logo]()
$257
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/205:00 pm
JAN
- ORD
1 stop6h 59m
Delta
Sat 5/2312:00 pm
ORD
- JAN
1 stop6h 52m
Delta
Deal found 4/21![Delta logo]()
$283
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:23 pm
JAN
- ORD
1 stop4h 36m
Delta
Mon 6/17:07 am
ORD
- JAN
1 stop5h 05m
Delta
Deal found 4/21![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:05 pm
JAN
- MDW
1 stop4h 04m
Delta
Mon 6/16:23 am
MDW
- JAN
1 stop5h 49m
Delta
Deal found 4/21![Delta logo]()
$328
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/302:55 pm
JAN
- ORD
1 stop6h 58m
Delta
Mon 6/15:30 am
ORD
- JAN
1 stop4h 34m
Delta
Deal found 4/21![Delta logo]()
$303
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/302:55 pm
JAN
- MDW
1 stop6h 14m
Delta
Mon 6/16:23 am
MDW
- JAN
1 stop5h 49m
Delta
Deal found 4/21![Delta logo]()
$303
One-way flights from Jackson to ChicagoSearch for one-way flight options from Jackson to Chicago. Find affordable one-way fares based on user searches. Data last updated April 24, 2026.
Search for one-way flight options from Jackson to Chicago. Find affordable one-way fares based on user searches. Data last updated April 24, 2026.
This American Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/237:29 pm
JAN
- ORD
1 stop5h 13m
American Airlines
Deal found 4/23![American Airlines logo]()
$152
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/236:10 pm
JAN
- MDW
1 stop4h 35m
Southwest
Deal found 4/23![Southwest logo]()
$152
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:39 pm
JAN
- ORD
1 stop5h 15m
American Airlines
Deal found 4/20![American Airlines logo]()
$186
This American Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
Sun 5/246:27 am
JAN
- ORD
1 stop6h 28m
American Airlines
Deal found 4/23![American Airlines logo]()
$194
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/315:35 am
JAN
- MDW
1 stop4h 25m
Delta
Deal found 4/23![Delta logo]()
$194
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
Sun 5/315:55 am
JAN
- ORD
2 stops9h 35m
Southwest
Deal found 4/23![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
Sun 5/315:55 am
JAN
- MDW
2 stops9h 35m
Southwest
Deal found 4/23![Southwest logo]()
$199
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:05 pm
JAN
- ORD
1 stop5h 43m
American Airlines
Deal found 4/19![American Airlines logo]()
$204
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
Sun 5/246:00 pm
JAN
- ORD
2 stops15h 45m
Southwest
Deal found 4/23![Southwest logo]()
$205
This American Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
Sun 5/315:29 pm
JAN
- ORD
1 stop7h 16m
American Airlines
Deal found 4/23![American Airlines logo]()
$214
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
Sun 5/241:20 pm
JAN
- MDW
2 stops9h 20m
Southwest
Deal found 4/23![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1911:25 am
JAN
- MDW
2 stops10h 35m
Southwest
Deal found 4/22![Southwest logo]()
$225
Find flight deals from Jackson to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Jackson (JAN) 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 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $251 (Delta) |
One-way from | $152 (American Airlines) |
Popular in | July |
Cheapest in | September |
Average price | $346 |
Cheapflights Fare Finder
Customize your flight search to find flights from Jackson 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 24, 2026.
Use the filters below to find and compare flights from Jackson to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Thu 8/20
6:59 pm-11:57 pm
1 stop4h 58m
Chicago O'Hare Intl
Sat 8/22
5:55 pm-11:19 pm
1 stop5h 24m
$303
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Sat 5/30
2:55 pm-9:53 pm
1 stop6h 58m
Chicago O'Hare Intl
Mon 6/1
5:30 am-10:04 am
1 stop4h 34m
$303
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Thu 8/20
2:40 pm-9:46 pm
1 stop7h 06m
Chicago Midway
Sat 8/22
10:35 am-3:53 pm
1 stop5h 18m
$303
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Mon 5/18
5:00 pm-9:53 pm
1 stop4h 53m
Chicago O'Hare Intl
Mon 5/25
5:30 am-10:04 am
1 stop4h 34m
$352
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Tue 5/19
1:00 pm-9:50 pm
2 stops8h 50m
Chicago Midway
Tue 5/26
11:35 am-8:20 pm
2 stops8h 45m
$372
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Tue 7/7
7:15 pm-11:50 pm
1 stop4h 35m
Chicago Midway
Sat 7/11
5:05 am-11:40 am
1 stop6h 35m
$387
Quickest round-trip
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Fri 7/10
7:10 pm-11:53 pm
1 stop4h 43m
Chicago O'Hare Intl
Tue 7/14
8:03 am-12:05 pm
1 stop4h 02m
$387
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Thu 10/15
2:40 pm-9:45 pm
1 stop7h 05m
Chicago Midway
Sun 10/18
6:00 am-11:22 am
1 stop5h 22m
$387
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Fri 6/12
5:10 am-3:55 pm
1 stop10h 45m
Chicago Midway
Mon 6/15
5:00 am-10:45 am
1 stop5h 45m
$392
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Fri 7/10
5:10 am-3:55 pm
2 stops10h 45m
Chicago Midway
Tue 7/14
3:10 pm-6:45 pm
1 stop3h 35m
$392
Showing 1-10 of 41 resultsSorted by cheapest first
Compare providers for flights from Jackson 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 Jackson to Chicago in April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Jackson, Mississippi-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jackson, Mississippi-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Jackson, Mississippi-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Jackson, Mississippi-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 Jackson, Mississippi-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 Jackson to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Jackson with our price prediction graph.
JAN-CHI
JAN-ORD
JAN-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 Jackson to Chicago
JAN-CHI
JAN-ORD
JAN-MDW
What is the cheapest month to book a flight from Jackson, Mississippi to Chicago?
Currently, September is the cheapest month in which you can book a flight from Jackson, Mississippi to Chicago (average of $191). Flying from Jackson, Mississippi to Chicago in April is currently the most expensive (average of $314). 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.
How much does it cost to fly round-trip from Jackson, Mississippi to Chicago?
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 24, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andAmerican Airlines from Jackson to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Jackson 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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Jackson and Chicago flights
Browse other Jackson and Chicago flight options. Last updated on April 24, 2026.
Other flights from Jackson
Browse through other flights departing from Jackson. Flights are based on user searches made on Cheapflights and were last updated on April 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Jackson to Chicago
Discover the top 3 airlines that operate flights from Jackson 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 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$196 | Average$413 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$234 | Average$406 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$258 | Average$453 | FlexibilityNo cancel fee | On-time71% |