$149+ 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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Mar 23 — Mar 301
Round-trip
1 adult, Economy
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Find cheap flights from Jackson 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
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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 February 21, 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 February 21, 2026.
This Delta deal was found by Cheapflights users on 2/19. 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 5/510:58 am
JAN
- ORD
1 stop5h 44m
Delta
Tue 5/127:05 am
ORD
- JAN
1 stop5h 08m
Delta
Deal found 2/19![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 2/20. 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 5/55:02 pm
JAN
- MDW
1 stop5h 26m
Delta
Tue 5/1210:46 am
MDW
- JAN
1 stop5h 30m
Delta
Deal found 2/20![Delta logo]()
$297
This American Airlines deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 3/166:42 pm
JAN
- ORD
1 stop5h 24m
American Airlines
Tue 3/1710:28 am
ORD
- JAN
1 stop6h 31m
American Airlines
Deal found 2/17![American Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 3/1612:20 pm
JAN
- MDW
1 stop5h 20m
Southwest
Tue 3/176:25 am
MDW
- JAN
1 stop5h 05m
Southwest
Deal found 2/17![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 3/1612:20 pm
JAN
- ORD
2 stops9h 35m
Southwest
Tue 3/172:40 pm
ORD
- JAN
1 stop3h 55m
Southwest
Deal found 2/17![Southwest logo]()
$314
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Tue 3/244:35 pm
JAN
- ORD
1 stop7h 01m
American Airlines
Fri 3/275:00 pm
ORD
- JAN
1 stop6h 44m
American Airlines
Deal found 2/19![American Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 3/245:07 pm
JAN
- MDW
1 stop5h 24m
Delta
Fri 3/276:00 am
MDW
- JAN
1 stop4h 08m
Delta
Deal found 2/17![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 2/20. 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.
Sun 4/125:55 am
JAN
- MDW
1 stop4h 40m
Southwest
Wed 4/1511:35 am
MDW
- JAN
2 stops8h 45m
Southwest
Deal found 2/20![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 2/20. 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.
Sun 4/125:55 am
JAN
- ORD
2 stops9h 35m
Southwest
Wed 4/1511:55 am
ORD
- JAN
2 stops8h 25m
Southwest
Deal found 2/20![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:45 pm
JAN
- MDW
2 stops9h 15m
Southwest
Wed 5/68:15 am
MDW
- JAN
2 stops9h 15m
Southwest
Deal found 2/18![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:30 am
JAN
- ORD
2 stops15h 25m
Southwest
Fri 4/242:40 pm
ORD
- JAN
1 stop4h 25m
Southwest
Deal found 2/18![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 5/157:45 pm
JAN
- MDW
2 stops9h 15m
Southwest
Tue 5/199:50 am
MDW
- JAN
1 stop7h 40m
Southwest
Deal found 2/17![Southwest logo]()
$343
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 February 21, 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 February 21, 2026.
This Delta deal was found by Cheapflights users on 2/20. 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 5/510:58 am
JAN
- ORD
1 stop5h 44m
Delta
Tue 5/128:10 am
ORD
- JAN
1 stop4h 03m
Delta
Deal found 2/20![Delta logo]()
$297
This American Airlines deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 5/22:20 pm
JAN
- ORD
1 stop6h 53m
American Airlines
Tue 5/56:04 am
ORD
- JAN
1 stop7h 46m
American Airlines
Deal found 2/17![American Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 3/1612:20 pm
JAN
- ORD
2 stops9h 35m
Southwest
Tue 3/172:40 pm
ORD
- JAN
1 stop3h 55m
Southwest
Deal found 2/17![Southwest logo]()
$314
This Delta deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/510:58 am
JAN
- MDW
1 stop5h 28m
Delta
Tue 5/1210:46 am
MDW
- JAN
1 stop5h 30m
Delta
Deal found 2/18![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 3/1612:20 pm
JAN
- MDW
1 stop5h 20m
Southwest
Tue 3/1710:30 am
MDW
- JAN
2 stops8h 05m
Southwest
Deal found 2/17![Southwest logo]()
$314
This Delta deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/15:35 am
JAN
- ORD
1 stop4h 24m
Delta
Sat 4/45:59 pm
ORD
- JAN
1 stop5h 25m
Delta
Deal found 2/18![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 5/26:00 am
JAN
- ORD
2 stops16h 20m
Southwest
Tue 5/511:55 am
ORD
- JAN
2 stops8h 25m
Southwest
Deal found 2/17![Southwest logo]()
$325
This Delta deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/112:54 pm
JAN
- ORD
1 stop7h 22m
Delta
Wed 5/67:10 am
ORD
- JAN
1 stop4h 58m
Delta
Deal found 2/18![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:45 am
JAN
- ORD
2 stops9h 45m
Southwest
Wed 5/611:55 am
ORD
- JAN
2 stops8h 25m
Southwest
Deal found 2/18![Southwest logo]()
$342
This Delta deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 5/157:24 pm
JAN
- ORD
1 stop4h 35m
Delta
Tue 5/196:00 am
ORD
- JAN
1 stop4h 04m
Delta
Deal found 2/17![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 5/157:45 pm
JAN
- MDW
2 stops9h 15m
Southwest
Tue 5/198:15 am
MDW
- JAN
2 stops9h 15m
Southwest
Deal found 2/17![Southwest logo]()
$342
This Delta deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/110:58 am
JAN
- MDW
1 stop5h 28m
Delta
Wed 5/66:00 am
MDW
- JAN
1 stop4h 13m
Delta
Deal found 2/18![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:45 pm
JAN
- MDW
2 stops9h 15m
Southwest
Wed 5/68:15 am
MDW
- JAN
2 stops9h 15m
Southwest
Deal found 2/18![Southwest logo]()
$342
This Delta deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 3/245:07 pm
JAN
- MDW
1 stop5h 24m
Delta
Fri 3/276:00 am
MDW
- JAN
1 stop4h 08m
Delta
Deal found 2/17![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:30 am
JAN
- ORD
2 stops15h 25m
Southwest
Fri 4/242:40 pm
ORD
- JAN
1 stop4h 25m
Southwest
Deal found 2/18![Southwest logo]()
$343
This Delta deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/107:24 pm
JAN
- ORD
1 stop4h 35m
Delta
Mon 5/118:10 am
ORD
- JAN
1 stop4h 03m
Delta
Deal found 2/18![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/112:05 pm
JAN
- ORD
2 stops9h 50m
Southwest
Sat 4/42:40 pm
ORD
- JAN
1 stop4h 55m
Southwest
Deal found 2/18![Southwest logo]()
$349
This Delta deal was found by Cheapflights users on 2/20. 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.
Sat 5/23:05 pm
JAN
- ORD
1 stop5h 11m
Delta
Mon 6/157:10 am
ORD
- JAN
1 stop4h 10m
Delta
Deal found 2/20![Delta logo]()
$356
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:30 am
JAN
- MDW
1 stop5h 10m
Southwest
Fri 4/241:10 pm
MDW
- JAN
2 stops7h 50m
Southwest
Deal found 2/18![Southwest logo]()
$357
Last-minute flights from Jackson to ChicagoDiscover last-minute flight deals from Jackson to Chicago. Data last updated February 21, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chicago. Data last updated February 21, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/410:57 am
JAN
- ORD
1 stop5h 54m
Delta
Sat 3/75:25 am
ORD
- JAN
1 stop6h 09m
Delta
Deal found 2/18![Delta logo]()
$447
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:40 am
JAN
- MDW
1 stop6h 50m
Southwest
Sat 3/73:00 pm
MDW
- JAN
1 stop6h 50m
Southwest
Deal found 2/18![Southwest logo]()
$447
This American Airlines deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:56 pm
JAN
- ORD
1 stop4h 59m
American Airlines
Wed 3/186:10 am
ORD
- JAN
1 stop5h 47m
American Airlines
Deal found 2/18![American Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 3/166:42 pm
JAN
- ORD
1 stop5h 24m
American Airlines
Tue 3/1710:28 am
ORD
- JAN
1 stop6h 31m
American Airlines
Deal found 2/17![American Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 3/1612:20 pm
JAN
- MDW
1 stop5h 20m
Southwest
Tue 3/176:25 am
MDW
- JAN
1 stop5h 05m
Southwest
Deal found 2/17![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 3/1612:20 pm
JAN
- ORD
2 stops9h 35m
Southwest
Tue 3/172:40 pm
ORD
- JAN
1 stop3h 55m
Southwest
Deal found 2/17![Southwest logo]()
$314
This American Airlines deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/204:35 pm
JAN
- ORD
1 stop7h 01m
American Airlines
Fri 3/275:00 pm
ORD
- JAN
1 stop6h 44m
American Airlines
Deal found 2/18![American Airlines logo]()
$431
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/205:30 am
JAN
- ORD
2 stops7h 20m
Southwest
Fri 3/272:40 pm
ORD
- JAN
1 stop5h 00m
Southwest
Deal found 2/18![Southwest logo]()
$433
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Tue 3/244:35 pm
JAN
- ORD
1 stop7h 01m
American Airlines
Fri 3/275:00 pm
ORD
- JAN
1 stop6h 44m
American Airlines
Deal found 2/19![American Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 3/245:07 pm
JAN
- MDW
1 stop5h 24m
Delta
Fri 3/276:00 am
MDW
- JAN
1 stop4h 08m
Delta
Deal found 2/17![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” 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 3/2412:05 pm
JAN
- ORD
2 stops9h 50m
Southwest
Fri 3/272:40 pm
ORD
- JAN
1 stop5h 00m
Southwest
Deal found 2/17![Southwest logo]()
$398
This Southwest deal was found by Cheapflights users on 2/19. 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 3/247:05 pm
JAN
- MDW
1 stop4h 50m
Southwest
Fri 3/272:20 pm
MDW
- JAN
2 stops7h 30m
Southwest
Deal found 2/19![Southwest logo]()
$423
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 February 21, 2026.
Search for one-way flight options from Jackson to Chicago. Find affordable one-way fares based on user searches. Data last updated February 21, 2026.
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 3/186:35 am
JAN
- ORD
1 stop6h 44m
American Airlines
Deal found 2/19![American Airlines logo]()
$149
This Delta deal was found by Cheapflights users on 2/19. 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.
Wed 3/1812:55 pm
JAN
- MDW
1 stop4h 27m
Delta
Deal found 2/19![Delta logo]()
$149
This Southwest deal was found by Cheapflights users on 2/19. 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.
Wed 3/1812:05 pm
JAN
- ORD
2 stops9h 50m
Southwest
Deal found 2/19![Southwest logo]()
$154
This Southwest deal was found by Cheapflights users on 2/19. 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.
Wed 3/1812:05 pm
JAN
- MDW
2 stops8h 45m
Southwest
Deal found 2/19![Southwest logo]()
$154
This Delta deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/197:06 pm
JAN
- ORD
1 stop4h 48m
Delta
Deal found 2/18![Delta logo]()
$161
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1912:20 pm
JAN
- ORD
2 stops9h 35m
Southwest
Deal found 2/18![Southwest logo]()
$166
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1912:20 pm
JAN
- MDW
1 stop5h 20m
Southwest
Deal found 2/18![Southwest logo]()
$178
This Delta deal was found by Cheapflights users on 2/20. 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.
Sat 3/289:55 am
JAN
- ORD
1 stop6h 54m
Delta
Deal found 2/20![Delta logo]()
$184
This Delta deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/110:58 am
JAN
- MDW
1 stop5h 28m
Delta
Deal found 2/18![Delta logo]()
$184
This Southwest deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/912:15 pm
JAN
- ORD
2 stops9h 40m
Southwest
Deal found 2/20![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/112:15 pm
JAN
- MDW
2 stops6h 00m
Southwest
Deal found 2/18![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/912:15 pm
JAN
- MDW
1 stop4h 45m
Southwest
Deal found 2/20![Southwest logo]()
$204
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 February 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $297 (Delta) |
One-way from | $149 (American Airlines) |
Popular in | April |
Cheapest in | September |
Average price | $406 |
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 February 21, 2026.
Use the filters below to find and compare flights from Jackson to Chicago that are best for you.
Fly from
Jackson
Fly to
Chicago
Route
Depart
Return
Price
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Tue 5/5
10:58 am-4:42 pm
1 stop5h 44m
Chicago O'Hare Intl
Tue 5/12
8:10 am-12:13 pm
1 stop4h 03m
$297
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Sat 5/2
2:20 pm-9:13 pm
1 stop6h 53m
Chicago O'Hare Intl
Tue 5/5
6:04 am-1:50 pm
1 stop7h 46m
$297
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Tue 5/5
10:58 am-4:26 pm
1 stop5h 28m
Chicago Midway
Tue 5/12
10:46 am-4:16 pm
1 stop5h 30m
$297
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Wed 4/1
5:35 am-9:59 am
1 stop4h 24m
Chicago O'Hare Intl
Sat 4/4
5:59 pm-11:24 pm
1 stop5h 25m
$309
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Mon 3/16
12:20 pm-9:55 pm
2 stops9h 35m
Chicago O'Hare Intl
Tue 3/17
2:40 pm-6:35 pm
1 stop3h 55m
$314
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Mon 3/16
12:20 pm-5:40 pm
1 stop5h 20m
Chicago Midway
Tue 3/17
10:30 am-6:35 pm
2 stops8h 05m
$314
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Sat 5/2
6:00 am-10:20 pm
2 stops16h 20m
Chicago O'Hare Intl
Tue 5/5
11:55 am-8:20 pm
2 stops8h 25m
$325
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Fri 5/1
12:54 pm-8:16 pm
1 stop7h 22m
Chicago O'Hare Intl
Wed 5/6
7:10 am-12:08 pm
1 stop4h 58m
$332
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Fri 5/15
7:24 pm-11:59 pm
1 stop4h 35m
Chicago O'Hare Intl
Tue 5/19
6:00 am-10:04 am
1 stop4h 04m
$332
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Fri 5/1
10:58 am-4:26 pm
1 stop5h 28m
Chicago Midway
Wed 5/6
6:00 am-10:13 am
1 stop4h 13m
$332
Showing 1-10 of 40 results
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 February.
| 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-MDW
JAN-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 Jackson to Chicago
JAN-CHI
JAN-MDW
JAN-ORD
What is the cheapest month to book a flight from Jackson, Mississippi to Chicago?
Currently, August is the cheapest month in which you can book a flight from Jackson, Mississippi to Chicago (average of $196). Flying from Jackson, Mississippi to Chicago in April is currently the most expensive (average of $338). 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 February 21, 2026.
Get a feel of what it's like to fly with Southwest, Delta, and American 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.
Overall
8.0
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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 February 21, 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 February 21, 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 February 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$196 | Average$419 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$234 | Average$406 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$258 | Average$401 | FlexibilityNo cancel fee | On-time71% |