$170+ 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 6/16. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Jun 13 — Jun 201
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
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.Cheap flight deals from Jackson to Chicago
Cheapest
Best
Last-minute
One-way
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 May 14, 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 May 14, 2026.
This American Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/104:21 pm
JAN
- ORD
1 stop5h 12m
American Airlines
Wed 6/175:34 pm
ORD
- JAN
1 stop6h 20m
American Airlines
Deal found 5/14![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/103:06 pm
JAN
- MDW
1 stop7h 11m
Delta
Tue 6/1612:50 pm
MDW
- JAN
1 stop5h 25m
Delta
Deal found 5/13![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 7/112:20 pm
JAN
- MDW
1 stop4h 45m
Southwest
Wed 7/1511:50 am
MDW
- JAN
1 stop6h 55m
Southwest
Deal found 5/13![Southwest logo]()
$344
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 7/15:04 pm
JAN
- ORD
1 stop6h 55m
Delta
Mon 7/136:35 am
ORD
- JAN
1 stop5h 30m
Delta
Deal found 5/13![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/107:15 pm
JAN
- MDW
1 stop4h 35m
Southwest
Sat 6/135:05 am
MDW
- JAN
1 stop6h 40m
Southwest
Deal found 5/13![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/295:10 am
JAN
- MDW
1 stop10h 45m
Southwest
Tue 7/77:10 am
MDW
- JAN
1 stop4h 35m
Southwest
Deal found 5/13![Southwest logo]()
$362
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 7/103:06 pm
JAN
- ORD
1 stop5h 27m
Delta
Tue 7/145:30 am
ORD
- JAN
1 stop6h 35m
Delta
Deal found 5/12![Delta logo]()
$363
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 7/103:06 pm
JAN
- MDW
1 stop7h 09m
Delta
Tue 7/146:00 am
MDW
- JAN
1 stop4h 00m
Delta
Deal found 5/13![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/107:15 pm
JAN
- MDW
1 stop4h 35m
Southwest
Wed 6/1711:25 am
MDW
- JAN
2 stops7h 20m
Southwest
Deal found 5/12![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 7/112:20 pm
JAN
- MDW
1 stop4h 45m
Southwest
Mon 7/131:00 pm
MDW
- JAN
2 stops8h 55m
Southwest
Deal found 5/12![Southwest logo]()
$368
This American Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/235:29 pm
JAN
- ORD
1 stop6h 03m
American Airlines
Fri 6/263:00 pm
ORD
- JAN
1 stop7h 43m
American Airlines
Deal found 5/14![American Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/55:05 pm
JAN
- ORD
1 stop4h 48m
Delta
Tue 6/95:30 am
ORD
- JAN
1 stop6h 40m
Delta
Deal found 5/10![Delta logo]()
$373
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 May 14, 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 May 14, 2026.
This American Airlines deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/104:21 pm
JAN
- ORD
1 stop7h 37m
American Airlines
Wed 6/175:00 am
ORD
- JAN
1 stop6h 54m
American Airlines
Deal found 5/12![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/25:05 pm
JAN
- ORD
1 stop5h 22m
Delta
Tue 6/96:35 am
ORD
- JAN
1 stop5h 35m
Delta
Deal found 5/12![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/295:10 am
JAN
- MDW
1 stop10h 45m
Southwest
Tue 7/77:10 am
MDW
- JAN
1 stop4h 35m
Southwest
Deal found 5/13![Southwest logo]()
$362
This United Airlines deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/22:07 pm
JAN
- ORD
1 stop9h 08m
United Airlines
Tue 6/96:20 am
ORD
- JAN
2 stops13h 50m
United Airlines
Deal found 5/12![United Airlines logo]()
$545
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/25:05 pm
JAN
- MDW
1 stop4h 04m
Delta
Tue 6/96:00 am
MDW
- JAN
1 stop4h 08m
Delta
Deal found 5/12![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 7/112:20 pm
JAN
- MDW
1 stop4h 45m
Southwest
Mon 7/131:00 pm
MDW
- JAN
2 stops8h 55m
Southwest
Deal found 5/11![Southwest logo]()
$368
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 7/15:04 pm
JAN
- ORD
1 stop6h 55m
Delta
Mon 7/135:30 am
ORD
- JAN
1 stop4h 30m
Delta
Deal found 5/11![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 7/1011:25 am
JAN
- MDW
1 stop6h 25m
Southwest
Tue 7/1411:25 am
MDW
- JAN
2 stops7h 20m
Southwest
Deal found 5/13![Southwest logo]()
$368
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 7/2210:46 am
JAN
- ORD
1 stop6h 26m
Delta
Fri 7/245:30 am
ORD
- JAN
1 stop4h 30m
Delta
Deal found 5/13![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/711:55 am
JAN
- MDW
1 stop9h 50m
Southwest
Tue 6/91:10 pm
MDW
- JAN
1 stop7h 30m
Southwest
Deal found 5/13![Southwest logo]()
$378
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 7/103:06 pm
JAN
- MDW
1 stop7h 09m
Delta
Tue 7/146:00 am
MDW
- JAN
1 stop4h 00m
Delta
Deal found 5/9![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/612:20 pm
JAN
- MDW
1 stop4h 40m
Southwest
Wed 6/105:05 am
MDW
- JAN
2 stops6h 40m
Southwest
Deal found 5/10![Southwest logo]()
$380
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/55:05 pm
JAN
- ORD
1 stop4h 48m
Delta
Tue 6/95:30 am
ORD
- JAN
1 stop6h 40m
Delta
Deal found 5/10![Delta logo]()
$373
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/1012:20 pm
JAN
- MDW
2 stops7h 35m
Southwest
Wed 6/175:05 am
MDW
- JAN
2 stops6h 40m
Southwest
Deal found 5/11![Southwest logo]()
$391
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 6/195:10 am
JAN
- MDW
2 stops8h 35m
Southwest
Wed 6/247:10 am
MDW
- JAN
1 stop4h 35m
Southwest
Deal found 5/9![Southwest logo]()
$392
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 stop6h 58m
Delta
Sun 6/75:30 am
ORD
- JAN
1 stop4h 38m
Delta
Deal found 5/13![Delta logo]()
$469
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 5/3012:20 pm
JAN
- ORD
2 stops9h 35m
Southwest
Mon 6/17:35 pm
ORD
- JAN
2 stops16h 45m
Southwest
Deal found 5/11![Southwest logo]()
$453
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/295:04 pm
JAN
- ORD
1 stop6h 55m
Delta
Tue 7/75:30 am
ORD
- JAN
1 stop6h 35m
Delta
Deal found 5/13![Delta logo]()
$469
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/197:00 pm
JAN
- ORD
1 stop4h 59m
Delta
Mon 6/225:30 am
ORD
- JAN
1 stop4h 38m
Delta
Deal found 5/10![Delta logo]()
$493
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 5/235:00 pm
JAN
- ORD
1 stop7h 07m
Delta
Tue 5/265:30 am
ORD
- JAN
1 stop4h 34m
Delta
Deal found 5/11![Delta logo]()
$562
Last-minute flights from Jackson to ChicagoDiscover last-minute flight deals from Jackson to Chicago. Data last updated May 14, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chicago. Data last updated May 14, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/55:05 pm
JAN
- ORD
1 stop4h 48m
Delta
Tue 6/95:30 am
ORD
- JAN
1 stop6h 40m
Delta
Deal found 5/10![Delta logo]()
$373
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 6/55:05 pm
JAN
- MDW
1 stop4h 04m
Delta
Tue 6/96:00 am
MDW
- JAN
1 stop4h 08m
Delta
Deal found 5/9![Delta logo]()
$373
This American Airlines deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/64:21 pm
JAN
- ORD
1 stop7h 37m
American Airlines
Wed 6/105:10 am
ORD
- JAN
1 stop5h 16m
American Airlines
Deal found 5/10![American Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/711:55 am
JAN
- MDW
1 stop9h 50m
Southwest
Tue 6/93:10 pm
MDW
- JAN
1 stop3h 35m
Southwest
Deal found 5/13![Southwest logo]()
$378
This American Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/85:29 pm
JAN
- ORD
1 stop6h 03m
American Airlines
Mon 6/155:34 pm
ORD
- JAN
1 stop6h 20m
American Airlines
Deal found 5/11![American Airlines logo]()
$375
This American Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/104:21 pm
JAN
- ORD
1 stop5h 12m
American Airlines
Wed 6/175:34 pm
ORD
- JAN
1 stop6h 20m
American Airlines
Deal found 5/14![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/103:06 pm
JAN
- MDW
1 stop7h 11m
Delta
Tue 6/1612:50 pm
MDW
- JAN
1 stop5h 25m
Delta
Deal found 5/13![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/107:15 pm
JAN
- MDW
1 stop4h 35m
Southwest
Wed 6/175:05 am
MDW
- JAN
2 stops6h 40m
Southwest
Deal found 5/14![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/107:15 pm
JAN
- MDW
1 stop4h 35m
Southwest
Sat 6/135:05 am
MDW
- JAN
1 stop6h 40m
Southwest
Deal found 5/13![Southwest logo]()
$357
This American Airlines deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/195:29 pm
JAN
- ORD
1 stop7h 10m
American Airlines
Tue 6/231:19 pm
ORD
- JAN
1 stop6h 40m
American Airlines
Deal found 5/12![American Airlines logo]()
$363
This American Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/235:29 pm
JAN
- ORD
1 stop6h 03m
American Airlines
Fri 6/263:00 pm
ORD
- JAN
1 stop7h 43m
American Airlines
Deal found 5/14![American Airlines logo]()
$370
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/295:10 am
JAN
- MDW
1 stop10h 45m
Southwest
Tue 7/77:10 am
MDW
- JAN
1 stop4h 35m
Southwest
Deal found 5/13![Southwest logo]()
$362
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 May 14, 2026.
Search for one-way flight options from Jackson to Chicago. Find affordable one-way fares based on user searches. Data last updated May 14, 2026.
This American Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/105:29 pm
JAN
- ORD
1 stop7h 10m
American Airlines
Deal found 5/11![American Airlines logo]()
$170
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/107:15 pm
JAN
- MDW
1 stop4h 35m
Southwest
Deal found 5/11![Southwest logo]()
$170
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/36:30 am
JAN
- MDW
2 stops8h 25m
Southwest
Deal found 5/12![Southwest logo]()
$175
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” 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 6/187:00 pm
JAN
- ORD
1 stop4h 59m
Delta
Deal found 5/14![Delta logo]()
$188
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 8/15:04 pm
JAN
- MDW
1 stop5h 11m
Delta
Deal found 5/10![Delta logo]()
$188
This American Airlines deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 5/12![American Airlines logo]()
$194
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 5/242:55 pm
JAN
- MDW
1 stop6h 14m
Delta
Deal found 5/12![Delta logo]()
$194
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 5/12![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 7/245:10 am
JAN
- MDW
2 stops7h 10m
Southwest
Deal found 5/12![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 5/12![Southwest logo]()
$239
This American Airlines deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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.
Thu 6/187:29 pm
JAN
- ORD
1 stop5h 10m
American Airlines
Deal found 5/12![American Airlines logo]()
$243
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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
2 stops8h 35m
Southwest
Deal found 5/13![Southwest logo]()
$260
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 May 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $339 (American Airlines) |
One-way from | $170 (American Airlines) |
Popular in | July |
Cheapest in | September |
Average price | $519 |
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 May 14, 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
Wed 6/10
4:21 pm-11:58 pm
1 stop7h 37m
Chicago O'Hare Intl
Wed 6/17
5:00 am-11:54 am
1 stop6h 54m
$339
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Tue 6/2
5:05 pm-10:27 pm
1 stop5h 22m
Chicago O'Hare Intl
Tue 6/9
6:35 am-12:10 pm
1 stop5h 35m
$339
Quickest round-trip
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Tue 6/2
5:05 pm-9:09 pm
1 stop4h 04m
Chicago Midway
Tue 6/9
6:00 am-10:08 am
1 stop4h 08m
$339
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Wed 7/1
5:04 pm-11:59 pm
1 stop6h 55m
Chicago O'Hare Intl
Mon 7/13
5:30 am-10:00 am
1 stop4h 30m
$357
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Mon 6/29
5:10 am-3:55 pm
1 stop10h 45m
Chicago Midway
Tue 7/7
7:10 am-11:45 am
1 stop4h 35m
$362
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Wed 7/22
10:46 am-5:12 pm
1 stop6h 26m
Chicago O'Hare Intl
Fri 7/24
5:30 am-10:00 am
1 stop4h 30m
$363
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Fri 7/10
3:06 pm-10:15 pm
1 stop7h 09m
Chicago Midway
Tue 7/14
6:00 am-10:00 am
1 stop4h 00m
$363
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Wed 7/1
12:20 pm-5:05 pm
1 stop4h 45m
Chicago Midway
Mon 7/13
1:00 pm-9:55 pm
2 stops8h 55m
$368
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Fri 7/10
11:25 am-5:50 pm
1 stop6h 25m
Chicago Midway
Tue 7/14
11:25 am-6:45 pm
2 stops7h 20m
$368
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Fri 6/5
5:05 pm-9:53 pm
1 stop4h 48m
Chicago O'Hare Intl
Tue 6/9
5:30 am-12:10 pm
1 stop6h 40m
$373
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 May.
| 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 May 14, 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
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
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
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Jackson
Popular flights
Alternative routes for Jackson to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 14, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Jackson to Chicago by cabin class
Find flights from Jackson to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Jackson and Chicago flights
Browse other Jackson and Chicago flight options. Last updated on May 14, 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 May 14, 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 May 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$196 | Average$385 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$234 | Average$406 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$258 | Average$466 | FlexibilityNo cancel fee | On-time71% |