$155+ Cheap flights from Jackson, MS (JAN) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Nov 14 — Nov 211
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 October 15, 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 October 15, 2026.
This Delta deal was found by Cheapflights users on 10/12. 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.
Wed 11/113:50 pm -
1 stop4h 59m
Tue 11/178:04 am -
1 stop6h 57m
Deal found 10/12![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 10/13. 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 11/113:50 pm -
1 stop7h 04m
Tue 11/176:00 am -
1 stop6h 40m
Deal found 10/13![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 10/14. 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 11/116:30 am -
2 stops9h 00m
Wed 11/1812:45 pm -
1 stop4h 50m
Deal found 10/14![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 10/14. 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.
Fri 11/68:15 pm -
1 stop4h 55m
Tue 11/107:35 am -
2 stops10h 00m
Deal found 10/14![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 10/14. 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 11/116:30 am -
2 stops9h 00m
Mon 11/167:35 am -
2 stops10h 00m
Deal found 10/14![Southwest logo]()
$325
This American Airlines deal was found by Cheapflights users on 10/12. 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.
Tue 10/275:46 pm -
1 stop5h 14m
Sat 10/313:50 pm -
1 stop7h 09m
Deal found 10/12![American Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 10/12. 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 10/2711:10 am -
1 stop5h 04m
Sat 10/316:04 am -
1 stop5h 45m
Deal found 10/12![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 10/13. 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.
Sun 11/225:06 pm -
1 stop6h 48m
Wed 12/25:30 am -
1 stop7h 14m
Deal found 10/13![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 10/13. 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.
Sun 11/225:06 pm -
1 stop5h 48m
Thu 12/36:00 am -
1 stop4h 29m
Deal found 10/13![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 10/12. 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.
Tue 10/276:40 am -
2 stops8h 50m
Sat 10/316:45 am -
1 stop4h 35m
Deal found 10/12![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 10/12. 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.
Thu 12/316:30 am -
2 stops9h 45m
Wed 1/68:05 am -
2 stops9h 25m
Deal found 10/12![Southwest logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/10. 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.
Fri 11/66:34 pm -
1 stop5h 27m
Sun 11/85:00 am -
1 stop6h 45m
Deal found 10/10![American Airlines logo]()
$341
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 October 15, 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 October 15, 2026.
This American Airlines deal was found by Cheapflights users on 10/10. 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.
Fri 11/64:52 pm -
1 stop5h 38m
Mon 11/94:40 pm -
1 stop6h 03m
Deal found 10/10![American Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 10/12. 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.
Thu 12/316:15 pm -
1 stop4h 50m
Wed 1/65:25 am -
1 stop6h 55m
Deal found 10/12![Southwest logo]()
$309
This Delta deal was found by Cheapflights users on 10/11. 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.
Sun 2/75:35 pm -
1 stop4h 35m
Tue 2/910:35 am -
1 stop5h 19m
Deal found 10/11![Delta logo]()
$341
This United Airlines deal was found by Cheapflights users on 10/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:23 pm -
1 stop6h 03m
Sat 11/285:30 am -
1 stop5h 45m
Deal found 10/10![United Airlines logo]()
$552
This Southwest deal was found by Cheapflights users on 10/14. 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.
Fri 12/41:10 pm -
1 stop5h 55m
Sun 12/65:15 am -
1 stop5h 50m
Deal found 10/14![Southwest logo]()
$341
This Delta deal was found by Cheapflights users on 10/13. 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 11/115:06 pm -
1 stop5h 48m
Wed 11/1810:34 am -
2 stops12h 31m
Deal found 10/13![Delta logo]()
$365
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/225:06 pm -
1 stop5h 48m
Thu 11/264:13 pm -
1 stop5h 26m
Deal found 10/15![Delta logo]()
$368
This Southwest deal was found by Cheapflights users on 10/13. 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 11/278:15 pm -
1 stop4h 55m
Fri 12/46:40 am -
1 stop5h 50m
Deal found 10/13![Southwest logo]()
$380
This Southwest deal was found by Cheapflights users on 10/14. 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.
Fri 11/611:45 am -
2 stops8h 50m
Tue 11/107:35 am -
2 stops10h 00m
Deal found 10/14![Southwest logo]()
$389
This Delta deal was found by Cheapflights users on 10/13. 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 11/237:51 am -
1 stop4h 29m
Tue 12/17:05 am -
2 stops12h 44m
Deal found 10/13![Delta logo]()
$405
This Southwest deal was found by Cheapflights users on 10/10. 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.
Fri 11/68:15 pm -
1 stop4h 55m
Mon 11/911:10 am -
2 stops8h 35m
Deal found 10/10![Southwest logo]()
$394
This United Airlines deal was found by Cheapflights users on 10/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/79:05 am -
2 stops11h 14m
Mon 11/98:10 pm -
2 stops15h 05m
Deal found 10/11![United Airlines logo]()
$556
This Delta deal was found by Cheapflights users on 10/11. 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.
Fri 10/303:33 pm -
1 stop5h 05m
Sun 11/16:30 am -
1 stop5h 19m
Deal found 10/11![Delta logo]()
$435
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Thu 12/315:20 pm -
2 stops15h 40m
Wed 1/68:10 pm -
2 stops15h 16m
Deal found 10/12![United Airlines logo]()
$573
This Delta deal was found by Cheapflights users on 10/12. 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.
Thu 11/125:30 am -
2 stops13h 00m
Sun 11/155:30 am -
1 stop4h 59m
Deal found 10/12![Delta logo]()
$437
This United Airlines deal was found by Cheapflights users on 10/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:50 am -
2 stops13h 29m
Sat 11/1412:40 pm -
1 stop9h 19m
Deal found 10/10![United Airlines logo]()
$574
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/221:20 pm -
1 stop5h 45m
Thu 11/268:00 am -
1 stop7h 01m
Deal found 10/15![Delta logo]()
$454
This United Airlines deal was found by Cheapflights users on 10/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:57 pm -
1 stop5h 58m
Fri 10/307:29 am -
1 stop5h 50m
Deal found 10/14![United Airlines logo]()
$591
This Delta deal was found by Cheapflights users on 10/10. 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.
Tue 10/203:33 pm -
1 stop5h 05m
Tue 10/276:30 am -
1 stop5h 44m
Deal found 10/10![Delta logo]()
$495
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2011:14 am -
1 stop5h 51m
Sat 11/285:30 am -
1 stop5h 01m
Deal found 10/15![Delta logo]()
$588
Last-minute flights from Jackson to ChicagoDiscover last-minute flight deals from Jackson to Chicago. Data last updated October 15, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chicago. Data last updated October 15, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/12. 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.
Tue 10/275:46 pm -
1 stop5h 14m
Sat 10/313:50 pm -
1 stop7h 09m
Deal found 10/12![American Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 10/12. 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 10/2711:10 am -
1 stop5h 04m
Sat 10/316:04 am -
1 stop5h 45m
Deal found 10/12![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 10/12. 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.
Tue 10/276:40 am -
2 stops8h 50m
Sat 10/316:45 am -
1 stop4h 35m
Deal found 10/12![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 10/14. 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.
Fri 11/68:15 pm -
1 stop4h 55m
Tue 11/107:35 am -
2 stops10h 00m
Deal found 10/14![Southwest logo]()
$320
This American Airlines deal was found by Cheapflights users on 10/10. 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.
Fri 11/66:34 pm -
1 stop5h 27m
Sun 11/85:00 am -
1 stop6h 45m
Deal found 10/10![American Airlines logo]()
$341
This Delta deal was found by Cheapflights users on 10/13. 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 11/611:10 am -
1 stop4h 07m
Sun 11/86:04 am -
1 stop4h 21m
Deal found 10/13![Delta logo]()
$341
This Delta deal was found by Cheapflights users on 10/12. 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.
Wed 11/119:16 am -
1 stop5h 33m
Thu 11/125:30 am -
1 stop4h 59m
Deal found 10/12![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 10/13. 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 11/113:50 pm -
1 stop7h 04m
Tue 11/176:00 am -
1 stop6h 40m
Deal found 10/13![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 10/14. 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 11/116:30 am -
2 stops9h 00m
Wed 11/1812:45 pm -
1 stop4h 50m
Deal found 10/14![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 10/14. 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 11/116:30 am -
2 stops9h 00m
Mon 11/167:35 am -
2 stops10h 00m
Deal found 10/14![Southwest logo]()
$325
This Delta deal was found by Cheapflights users on 10/13. 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.
Sun 11/225:06 pm -
1 stop6h 48m
Thu 12/38:04 am -
1 stop6h 57m
Deal found 10/13![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 10/13. 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.
Sun 11/225:06 pm -
1 stop5h 48m
Thu 12/36:00 am -
1 stop4h 29m
Deal found 10/13![Delta logo]()
$329
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 October 15, 2026.
Search for one-way flight options from Jackson to Chicago. Find affordable one-way fares based on user searches. Data last updated October 15, 2026.
This Delta deal was found by Cheapflights users on 10/13. 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 11/235:30 am -
1 stop6h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Delta logo]()
$155
This Delta deal was found by Cheapflights users on 10/13. 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 11/235:30 am -
1 stop6h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Delta logo]()
$155
This Southwest deal was found by Cheapflights users on 10/12. 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.
Tue 11/36:30 am -
2 stops9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Southwest logo]()
$160
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/215:06 pm -
1 stop6h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$174
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/185:06 pm -
1 stop5h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$174
This Delta deal was found by Cheapflights users on 10/13. 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.
Sun 11/225:06 pm -
1 stop6h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Delta logo]()
$175
This Delta deal was found by Cheapflights users on 10/13. 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.
Sun 11/225:06 pm -
1 stop5h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Delta logo]()
$175
This Delta deal was found by Cheapflights users on 10/11. 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.
Sun 11/11:04 pm -
1 stop6h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Delta logo]()
$187
This Delta deal was found by Cheapflights users on 10/11. 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.
Sun 11/13:33 pm -
1 stop7h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 10/12. 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 12/115:40 am -
2 stops10h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Southwest logo]()
$192
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/197:30 pm -
1 stop4h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$194
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/195:06 pm -
1 stop5h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$194
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 October 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $309 (Delta) |
One-way from | $155 (Delta) |
Popular in | June |
Cheapest in | April |
Average price | $420 |
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 7,457,451 searches. Data last updated October 15, 2026.
Use the filters below to find and compare flights from Jackson to Chicago that are best for you.
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Cheapest round-trip
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Mon 11/23
5:30 am-12:20 pm
1 stop6h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Wed 12/9
6:15 pm-11:05 pm
1 stop4h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Tue 11/3
11:10 am-5:47 pm
1 stop6h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Wed 11/25
3:50 pm-8:49 pm
1 stop4h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Thu 12/10
7:24 pm-11:56 pm
1 stop4h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Fri 12/18
11:14 am-5:06 pm
1 stop5h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Sat 12/12
5:11 pm-11:56 pm
1 stop6h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Sat 11/21
1:20 pm-7:05 pm
1 stop5h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Tue 11/3
4:00 pm-10:33 pm
1 stop6h 33m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Mon 11/23
5:30 am-10:24 am
1 stop4h 54m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
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 October.
| 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, January is the cheapest month in which you can book a flight from Jackson, Mississippi to Chicago (average of $358). Flying from Jackson, Mississippi to Chicago in June is currently the most expensive (average of $674). 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?
Airfare is below average for this route at the moment.
Jackson, Mississippi to Chicago flights typically cost between $330 and $520 in November.The cheapest round-trip price found within the last 5 days was $309 on Delta (Nov 11-Nov 17).
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 October 15, 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
Overall
7.9
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from 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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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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 October 15, 2026.
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Jackson and Chicago flights
Browse other Jackson and Chicago flight options. Last updated on October 15, 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 October 15, 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 7,457,451 searches. Data last updated October 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$286 | Average$409 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$296 | Average$543 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$308 | Average$428 | FlexibilityNo cancel fee | On-time63% |