$123+ Cheap flights from Chicago (CHI) to Jackson, MS (JAN)
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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAN
Oct 22 — Oct 291
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Jackson 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 Chicago to JacksonExplore the most affordable flight options available from Chicago to Jackson. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 22, 2026.
Explore the most affordable flight options available from Chicago to Jackson. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 22, 2026.
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/171:46 pm -
1 stop7h 06m
Sat 10/245:40 am -
1 stop6h 28m
Deal found 9/17![American Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 9/18. 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 11/1110:32 am -
1 stop4h 29m
Mon 11/1611:14 am -
1 stop5h 51m
Deal found 9/18![Delta logo]()
$292
This Delta deal was found by Cheapflights users on 9/18. 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 11/116:00 am -
1 stop4h 29m
Mon 11/165:06 pm -
1 stop5h 48m
Deal found 9/18![Delta logo]()
$292
This American Airlines deal was found by Cheapflights users on 9/19. 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 11/115:19 am -
1 stop6h 37m
Mon 11/164:52 pm -
1 stop6h 23m
Deal found 9/19![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 9/17. 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 10/95:27 am -
1 stop4h 58m
Tue 10/137:45 am -
1 stop4h 28m
Deal found 9/17![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 9/17. 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 10/176:55 am -
2 stops7h 50m
Sat 10/2412:30 pm -
1 stop7h 30m
Deal found 9/17![Southwest logo]()
$327
This KAYAK deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:30 am -
1 stop5h 19m
Tue 11/34:00 pm -
1 stop4h 38m
Deal found 9/21![Delta logo]()
$328
This KAYAK deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:04 am -
1 stop5h 45m
Tue 11/34:00 pm -
1 stop6h 33m
Deal found 9/21![Delta logo]()
$328
This American Airlines deal was found by Cheapflights users on 9/18. 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 11/63:52 pm -
1 stop7h 00m
Mon 11/95:48 pm -
1 stop6h 13m
Deal found 9/18![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:04 am -
1 stop5h 45m
Sat 11/711:10 am -
1 stop4h 07m
Deal found 9/20![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 9/18. 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 11/67:30 am -
2 stops14h 40m
Mon 11/98:15 pm -
1 stop4h 55m
Deal found 9/18![Southwest logo]()
$340
This Delta deal was found by Cheapflights users on 9/20. 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 11/245:30 am -
1 stop7h 10m
Thu 11/266:00 am -
1 stop6h 23m
Deal found 9/20![Delta logo]()
$343
Best flights from Chicago to JacksonDiscover carefully curated flight deals from Chicago to Jackson that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.
Discover carefully curated flight deals from Chicago to Jackson that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:27 am -
1 stop4h 27m
Sat 11/71:04 pm -
1 stop7h 34m
Deal found 9/20![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 9/17. 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 10/178:40 am -
1 stop6h 05m
Sat 10/2412:30 pm -
1 stop7h 30m
Deal found 9/17![Southwest logo]()
$332
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:22 pm -
1 stop6h 04m
Mon 11/95:23 pm -
2 stops21h 12m
Deal found 9/18![United Airlines logo]()
$560
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:04 am -
1 stop6h 10m
Thu 10/225:02 pm -
1 stop5h 31m
Deal found 9/20![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:00 am -
1 stop4h 29m
Mon 11/165:06 pm -
1 stop5h 48m
Deal found 9/21![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 9/18. 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 11/67:30 am -
2 stops14h 40m
Mon 11/98:15 pm -
1 stop4h 55m
Deal found 9/18![Southwest logo]()
$340
This Delta deal was found by Cheapflights users on 9/17. 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 10/95:27 am -
1 stop4h 58m
Tue 10/137:45 am -
1 stop4h 28m
Deal found 9/17![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 9/20. 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 11/511:10 am -
2 stops8h 35m
Sat 11/76:30 am -
2 stops8h 15m
Deal found 9/20![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:20 pm -
1 stop4h 45m
Sun 12/135:40 am -
2 stops10h 05m
Deal found 9/21![Southwest logo]()
$378
This Delta deal was found by Cheapflights users on 9/19. 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.
Fri 12/116:15 pm -
1 stop4h 50m
Sun 12/137:24 pm -
1 stop4h 28m
Deal found 9/19![Delta logo]()
$373
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/193:45 pm -
1 stop6h 10m
Mon 10/265:55 am -
2 stops9h 10m
Deal found 9/19![Southwest logo]()
$400
This Delta deal was found by Cheapflights users on 9/17. 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 10/95:27 am -
1 stop6h 47m
Mon 10/125:02 pm -
1 stop6h 55m
Deal found 9/17![Delta logo]()
$374
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/314:07 pm -
1 stop5h 52m
Tue 11/311:57 am -
1 stop7h 58m
Deal found 9/21![United Airlines logo]()
$564
This Southwest deal was found by Cheapflights users on 9/20. 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.
Fri 11/65:20 pm -
1 stop4h 50m
Sun 11/88:15 pm -
1 stop4h 55m
Deal found 9/20![Southwest logo]()
$407
This Southwest deal was found by Cheapflights users on 9/19. 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 11/312:45 pm -
1 stop4h 50m
Fri 11/68:15 pm -
1 stop4h 55m
Deal found 9/19![Southwest logo]()
$409
This Delta deal was found by Cheapflights users on 9/17. 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.
Thu 10/15:30 am -
1 stop6h 47m
Sat 10/35:14 pm -
1 stop6h 45m
Deal found 9/17![Delta logo]()
$497
Last-minute flights from Chicago to JacksonDiscover last-minute flight deals from Chicago to Jackson. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Jackson. Data last updated September 22, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/17. 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.
Thu 10/86:04 am -
1 stop6h 10m
Mon 10/125:02 pm -
1 stop5h 31m
Deal found 9/17![Delta logo]()
$417
This Delta deal was found by Cheapflights users on 9/17. 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 10/95:27 am -
1 stop4h 58m
Tue 10/137:45 am -
1 stop4h 28m
Deal found 9/17![Delta logo]()
$311
This Delta deal was found by Cheapflights users on 9/18. 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 10/95:27 am -
1 stop4h 58m
Mon 10/127:29 pm -
1 stop4h 28m
Deal found 9/18![Delta logo]()
$363
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Thu 10/155:00 am -
1 stop6h 45m
Thu 10/226:45 pm -
1 stop5h 23m
Deal found 9/17![American Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/171:46 pm -
1 stop7h 06m
Sat 10/245:40 am -
1 stop6h 28m
Deal found 9/17![American Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 9/17. 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 10/176:55 am -
2 stops7h 50m
Sat 10/2412:30 pm -
1 stop7h 30m
Deal found 9/17![Southwest logo]()
$327
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:40 pm -
1 stop5h 15m
Mon 10/264:46 pm -
1 stop5h 24m
Deal found 9/19![American Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/193:45 pm -
1 stop6h 10m
Mon 10/265:55 am -
2 stops9h 10m
Deal found 9/21![Southwest logo]()
$386
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/203:50 pm -
1 stop7h 09m
Sun 10/256:45 pm -
1 stop5h 23m
Deal found 9/20![American Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 9/20. 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.
Tue 10/202:10 pm -
1 stop3h 50m
Sun 10/258:25 pm -
1 stop4h 35m
Deal found 9/20![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 9/18. 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 10/216:25 am -
1 stop5h 50m
Sun 10/258:25 pm -
1 stop4h 35m
Deal found 9/18![Southwest logo]()
$412
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:04 am -
1 stop6h 10m
Thu 10/225:02 pm -
1 stop5h 31m
Deal found 9/20![Delta logo]()
$309
One-way flights from Chicago to JacksonSearch for one-way flight options from Chicago to Jackson. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
Search for one-way flight options from Chicago to Jackson. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Southwest deal was found by Cheapflights users on 9/17. 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 10/316:45 am -
1 stop4h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$123
This Delta deal was found by Cheapflights users on 9/17. 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.
Wed 10/215:27 am -
1 stop6h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$146
This KAYAK deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:27 am -
1 stop4h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$164
This Delta deal was found by Cheapflights users on 9/17. 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.
Mon 10/265:09 pm -
1 stop6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$164
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:30 am -
1 stop5h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$175
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:15 am -
1 stop5h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$187
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/176:00 am -
1 stop5h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![American Airlines logo]()
$189
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/263:50 pm -
1 stop7h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![American Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 9/17. 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 10/176:55 am -
2 stops7h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$204
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:20 pm -
1 stop4h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$215
This KAYAK deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:27 am -
1 stop4h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$226
This Delta deal was found by Cheapflights users on 9/19. 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.
Sat 10/35:30 am -
1 stop4h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Delta logo]()
$249
Find flight deals from Chicago to Jackson
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Jackson (JAN). 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 September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $291 (American Airlines) |
One-way from | $123 (Southwest) |
Popular in | December |
Cheapest in | August |
Average price | $588 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Jackson 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 September 22, 2026.
Use the filters below to find and compare flights from Chicago to Jackson that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Sat 10/31
6:45 am-11:20 am
1 stop4h 35m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$123
ChicagoJackson
ORD Chicago O'Hare Intl - JAN Jackson-Evers Intl
ORDJAN
Chicago O'Hare Intl
Wed 10/21
5:27 am-12:14 pm
1 stop6h 47m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$146
Quickest round-trip
ChicagoJackson
ORD Chicago O'Hare Intl - JAN Jackson-Evers Intl
ORDJAN
Chicago O'Hare Intl
Tue 11/3
5:27 am-9:54 am
1 stop4h 27m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$164
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Mon 10/26
5:09 pm-11:09 pm
1 stop6h 00m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$164
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Tue 11/3
11:39 am-6:44 pm
1 stop7h 05m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$164
ChicagoJackson
ORD Chicago O'Hare Intl - JAN Jackson-Evers Intl
ORDJAN
Chicago O'Hare Intl
Thu 10/22
6:30 am-12:14 pm
1 stop5h 44m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$175
ChicagoJackson
ORD Chicago O'Hare Intl - JAN Jackson-Evers Intl
ORDJAN
Chicago O'Hare Intl
Fri 12/4
11:35 am-4:24 pm
1 stop4h 49m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$175
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Sat 10/17
6:55 am-2:45 pm
2 stops7h 50m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$204
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Mon 11/2
5:20 pm-10:05 pm
1 stop4h 45m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$215
ChicagoJackson
ORD Chicago O'Hare Intl - JAN Jackson-Evers Intl
ORDJAN
Chicago O'Hare Intl
Mon 11/2
5:27 am-9:54 am
1 stop4h 27m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$226
Showing 1-10 of 38 resultsSorted by cheapest first
Compare providers for flights from Chicago to Jackson
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 Chicago to Jackson in September.
| 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 Chicago-Jackson, Mississippi flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Jackson, Mississippi flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Jackson, Mississippi flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Jackson, Mississippi 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 Chicago-Jackson, Mississippi 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 Chicago to Jackson
Have a flexible travel schedule? Discover the best time to fly to Jackson from Chicago with our price prediction graph.
CHI-JAN
ORD-JAN
MDW-JAN
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 Chicago to Jackson
CHI-JAN
ORD-JAN
MDW-JAN
What is the cheapest month to book a flight from Chicago to Jackson, Mississippi?
Currently, January is the cheapest month in which you can book a flight from Chicago to Jackson, Mississippi (average of $300). Flying from Chicago to Jackson, Mississippi in September is currently the most expensive (average of $588). 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 Chicago to Jackson, Mississippi?
Airfare is below average for this route at the moment.
Chicago to Jackson, Mississippi flights typically cost between $389 and $609 in October.The cheapest round-trip price found within the last 5 days was $291 on American Airlines (Oct 17-Oct 24).
Reviews of airlines servicing Jackson
Get insights into the airlines that provide service to Jackson. 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 Jackson. Reviews last updated September 22, 2026.
Read reviews from past customers who have flown Southwest,Delta, andAmerican Airlines from Chicago to Jackson. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Jackson. 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 Jackson?
Book flights to Jackson if you plan to visit one of these locationsVicksburg
Flowood
Clinton
Pearl
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Other flights to Jackson
Explore flights to Jackson departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 22, 2026.
Chicago and Jackson flights
Browse other Chicago and Jackson flight options. Last updated on September 22, 2026.
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Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on September 22, 2026.
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Top 3 airlines flying from Chicago to Jackson
Discover the top 3 airlines that operate flights from Chicago to Jackson. 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 September 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$270 | Average$388 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$308 | Average$562 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$366 | Average$502 | FlexibilityNo cancel fee | On-time71% |