$209+ Cheap flights from Chicago (CHI) to Jackson, MS (JAN)
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 7/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAN
Jul 24 — Jul 311
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 June 24, 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 June 24, 2026.
This American Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:00 am
ORD
- JAN
1 stop6h 53m
American Airlines
Tue 8/45:26 pm
JAN
- ORD
1 stop7h 17m
American Airlines
Deal found 6/23![American Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
MDW
- JAN
1 stop4h 00m
Delta
Tue 7/285:30 am
JAN
- MDW
1 stop4h 35m
Delta
Deal found 6/23![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 6/19. 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 10/206:05 am
MDW
- JAN
1 stop6h 25m
Southwest
Tue 10/271:05 pm
JAN
- MDW
2 stops8h 45m
Southwest
Deal found 6/19![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/85:30 am
ORD
- JAN
1 stop6h 29m
Delta
Mon 8/107:00 pm
JAN
- ORD
1 stop4h 57m
Delta
Deal found 6/21![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/84:39 pm
MDW
- JAN
1 stop4h 13m
Delta
Mon 8/105:32 am
JAN
- MDW
1 stop4h 27m
Delta
Deal found 6/23![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/88:05 am
MDW
- JAN
1 stop5h 50m
Southwest
Mon 8/105:55 am
JAN
- MDW
2 stops8h 15m
Southwest
Deal found 6/23![Southwest logo]()
$319
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:54 am
ORD
- JAN
1 stop6h 22m
Delta
Mon 8/245:01 pm
JAN
- ORD
1 stop6h 56m
Delta
Deal found 6/22![Delta logo]()
$325
This American Airlines deal was found by Cheapflights users on 6/19. 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 7/155:00 am
ORD
- JAN
1 stop6h 49m
American Airlines
Sun 7/197:26 pm
JAN
- ORD
1 stop5h 24m
American Airlines
Deal found 6/19![American Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 6/20. 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.
Fri 8/146:05 am
MDW
- JAN
1 stop6h 07m
Delta
Tue 8/1811:24 am
JAN
- MDW
1 stop4h 51m
Delta
Deal found 6/20![Delta logo]()
$345
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:00 am
ORD
- JAN
1 stop7h 17m
Delta
Sun 7/195:04 pm
JAN
- ORD
1 stop6h 49m
Delta
Deal found 6/20![Delta logo]()
$355
This Southwest deal was found by Cheapflights users on 6/19. 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 7/147:10 am
MDW
- JAN
1 stop4h 35m
Southwest
Tue 7/217:15 pm
JAN
- MDW
1 stop4h 40m
Southwest
Deal found 6/19![Southwest logo]()
$355
This American Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/75:05 am
ORD
- JAN
1 stop6h 31m
American Airlines
Mon 8/105:28 pm
JAN
- ORD
1 stop6h 02m
American Airlines
Deal found 6/21![American Airlines logo]()
$356
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 June 24, 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 June 24, 2026.
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:30 am
ORD
- JAN
1 stop6h 42m
Delta
Sat 8/88:00 am
JAN
- ORD
1 stop6h 48m
Delta
Deal found 6/22![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/88:05 am
MDW
- JAN
1 stop5h 50m
Southwest
Mon 8/105:55 am
JAN
- MDW
2 stops8h 15m
Southwest
Deal found 6/23![Southwest logo]()
$319
This American Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:45 pm
ORD
- JAN
1 stop7h 03m
American Airlines
Mon 7/67:26 pm
JAN
- ORD
1 stop5h 24m
American Airlines
Deal found 6/21![American Airlines logo]()
$472
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/252:16 pm
ORD
- JAN
1 stop20h 59m
United Airlines
Wed 8/265:20 pm
JAN
- ORD
1 stop14h 35m
United Airlines
Deal found 6/23![United Airlines logo]()
$473
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:05 am
MDW
- JAN
1 stop6h 07m
Delta
Sat 8/810:36 am
JAN
- MDW
1 stop5h 02m
Delta
Deal found 6/22![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 6/19. 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 7/147:10 am
MDW
- JAN
1 stop4h 35m
Southwest
Tue 7/217:15 pm
JAN
- MDW
1 stop4h 40m
Southwest
Deal found 6/19![Southwest logo]()
$355
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:54 am
ORD
- JAN
1 stop6h 22m
Delta
Mon 8/245:01 pm
JAN
- ORD
1 stop6h 56m
Delta
Deal found 6/22![Delta logo]()
$325
This Delta deal was found by Cheapflights users on 6/20. 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.
Fri 8/146:05 am
MDW
- JAN
1 stop6h 07m
Delta
Tue 8/1811:24 am
JAN
- MDW
1 stop4h 51m
Delta
Deal found 6/20![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:30 am
MDW
- JAN
2 stops6h 30m
Southwest
Sun 9/61:25 pm
JAN
- MDW
2 stops7h 30m
Southwest
Deal found 6/19![Southwest logo]()
$398
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:00 pm
MDW
- JAN
1 stop8h 45m
Southwest
Mon 7/2011:25 am
JAN
- MDW
2 stops8h 40m
Southwest
Deal found 6/19![Southwest logo]()
$417
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:10 am
MDW
- JAN
1 stop4h 35m
Southwest
Thu 7/2311:25 am
JAN
- MDW
1 stop6h 25m
Southwest
Deal found 6/22![Southwest logo]()
$461
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/39:48 am
ORD
- JAN
1 stop4h 38m
Delta
Sun 7/53:06 pm
JAN
- ORD
1 stop5h 26m
Delta
Deal found 6/21![Delta logo]()
$472
This Southwest deal was found by Cheapflights users on 6/21. 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.
Thu 7/162:45 pm
MDW
- JAN
2 stops7h 15m
Southwest
Sun 7/1911:55 am
JAN
- MDW
1 stop7h 35m
Southwest
Deal found 6/21![Southwest logo]()
$504
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/19:48 am
ORD
- JAN
1 stop4h 38m
Delta
Mon 7/67:00 pm
JAN
- ORD
1 stop4h 59m
Delta
Deal found 6/23![Delta logo]()
$567
This Delta deal was found by Cheapflights users on 6/19. 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 7/175:30 am
ORD
- JAN
1 stop4h 30m
Delta
Fri 7/247:10 pm
JAN
- ORD
1 stop4h 43m
Delta
Deal found 6/19![Delta logo]()
$569
Last-minute flights from Chicago to JacksonDiscover last-minute flight deals from Chicago to Jackson. Data last updated June 24, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Jackson. Data last updated June 24, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/19. 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 6/307:10 am
MDW
- JAN
1 stop4h 35m
Southwest
Tue 7/287:15 pm
JAN
- MDW
1 stop4h 40m
Southwest
Deal found 6/19![Southwest logo]()
$390
This American Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/115:00 am
ORD
- JAN
1 stop6h 53m
American Airlines
Sat 7/185:26 pm
JAN
- ORD
1 stop6h 13m
American Airlines
Deal found 6/23![American Airlines logo]()
$385
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:45 pm
ORD
- JAN
1 stop6h 03m
American Airlines
Tue 7/214:24 pm
JAN
- ORD
1 stop5h 36m
American Airlines
Deal found 6/19![American Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 6/19. 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 7/147:10 am
MDW
- JAN
1 stop4h 35m
Southwest
Tue 7/217:15 pm
JAN
- MDW
1 stop4h 40m
Southwest
Deal found 6/19![Southwest logo]()
$355
This American Airlines deal was found by Cheapflights users on 6/19. 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 7/155:00 am
ORD
- JAN
1 stop6h 49m
American Airlines
Sun 7/197:26 pm
JAN
- ORD
1 stop5h 24m
American Airlines
Deal found 6/19![American Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:00 pm
MDW
- JAN
1 stop8h 45m
Southwest
Mon 7/2011:25 am
JAN
- MDW
2 stops8h 40m
Southwest
Deal found 6/19![Southwest logo]()
$417
This American Airlines deal was found by Cheapflights users on 6/19. 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.
Thu 7/165:00 am
ORD
- JAN
1 stop6h 53m
American Airlines
Mon 7/207:26 pm
JAN
- ORD
1 stop5h 24m
American Airlines
Deal found 6/19![American Airlines logo]()
$397
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:00 am
ORD
- JAN
1 stop7h 17m
Delta
Sun 7/195:04 pm
JAN
- ORD
1 stop6h 49m
Delta
Deal found 6/20![Delta logo]()
$355
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
MDW
- JAN
1 stop4h 00m
Delta
Tue 7/285:30 am
JAN
- MDW
1 stop4h 35m
Delta
Deal found 6/23![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/213:10 pm
MDW
- JAN
1 stop3h 35m
Southwest
Tue 7/2812:20 pm
JAN
- MDW
2 stops7h 35m
Southwest
Deal found 6/23![Southwest logo]()
$360
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:10 am
MDW
- JAN
1 stop4h 35m
Southwest
Thu 7/235:10 am
JAN
- MDW
2 stops8h 35m
Southwest
Deal found 6/22![Southwest logo]()
$411
This American Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/314:51 pm
ORD
- JAN
1 stop4h 53m
American Airlines
Sun 8/25:22 am
JAN
- ORD
1 stop5h 48m
American Airlines
Deal found 6/21![American Airlines logo]()
$387
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 June 24, 2026.
Search for one-way flight options from Chicago to Jackson. Find affordable one-way fares based on user searches. Data last updated June 24, 2026.
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/171:00 pm
MDW
- JAN
2 stops9h 00m
Southwest
Deal found 6/23![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/163:00 pm
MDW
- JAN
1 stop7h 00m
Southwest
Deal found 6/22![Southwest logo]()
$214
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/95:30 am
ORD
- JAN
1 stop6h 35m
Delta
Deal found 6/23![Delta logo]()
$234
This Southwest deal was found by Cheapflights users on 6/19. 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.
Sat 7/49:00 am
MDW
- JAN
1 stop6h 15m
Southwest
Deal found 6/19![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/19:48 am
ORD
- JAN
1 stop4h 38m
Delta
Deal found 6/23![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/125:00 am
MDW
- JAN
2 stops6h 20m
Southwest
Deal found 6/23![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 6/19. 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.
Sun 8/26:00 am
MDW
- JAN
1 stop4h 00m
Delta
Deal found 6/19![Delta logo]()
$250
This Southwest deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:10 am
MDW
- JAN
1 stop4h 35m
Southwest
Deal found 6/21![Southwest logo]()
$267
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/175:30 am
ORD
- JAN
1 stop5h 54m
United Airlines
Deal found 6/23![United Airlines logo]()
$268
This United Airlines deal was found by Cheapflights users on 6/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/15:30 am
ORD
- JAN
1 stop5h 54m
United Airlines
Deal found 6/19![United Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 6/20. 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.
Sat 6/275:05 am
MDW
- JAN
1 stop6h 40m
Southwest
Deal found 6/20![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/201:00 pm
MDW
- JAN
2 stops9h 00m
Southwest
Deal found 6/22![Southwest logo]()
$285
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 June 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $303 (American Airlines) |
One-way from | $209 (Southwest) |
Popular in | December |
Cheapest in | January |
Average price | $561 |
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 2,558,603 searches. Data last updated June 24, 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
ORD - JAN
ORDJAN
Chicago O'Hare Intl
Tue 8/4
5:30 am-12:12 pm
1 stop6h 42m
Jackson-Evers Intl
Sat 8/8
8:00 am-2:48 pm
1 stop6h 48m
$303
ChicagoJackson
MDW - JAN
MDWJAN
Chicago Midway
Tue 8/4
6:05 am-12:12 pm
1 stop6h 07m
Jackson-Evers Intl
Sat 8/8
10:36 am-3:38 pm
1 stop5h 02m
$303
ChicagoJackson
MDW - JAN
MDWJAN
Chicago Midway
Sat 8/8
8:05 am-1:55 pm
1 stop5h 50m
Jackson-Evers Intl
Mon 8/10
5:55 am-2:10 pm
2 stops8h 15m
$319
ChicagoJackson
ORD - JAN
ORDJAN
Chicago O'Hare Intl
Thu 8/20
9:54 am-4:16 pm
1 stop6h 22m
Jackson-Evers Intl
Mon 8/24
5:01 pm-11:57 pm
1 stop6h 56m
$325
ChicagoJackson
MDW - JAN
MDWJAN
Chicago Midway
Fri 8/14
6:05 am-12:12 pm
1 stop6h 07m
Jackson-Evers Intl
Tue 8/18
11:24 am-4:15 pm
1 stop4h 51m
$345
ChicagoJackson
MDW - JAN
MDWJAN
Chicago Midway
Tue 7/14
7:10 am-11:45 am
1 stop4h 35m
Jackson-Evers Intl
Tue 7/21
7:15 pm-11:55 pm
1 stop4h 40m
$355
ChicagoJackson
MDW - JAN
MDWJAN
Chicago Midway
Fri 9/4
5:30 am-12:00 pm
2 stops6h 30m
Jackson-Evers Intl
Sun 9/6
1:25 pm-8:55 pm
2 stops7h 30m
$398
ChicagoJackson
MDW - JAN
MDWJAN
Chicago Midway
Wed 7/15
12:00 pm-8:45 pm
1 stop8h 45m
Jackson-Evers Intl
Mon 7/20
11:25 am-8:05 pm
2 stops8h 40m
$417
ChicagoJackson
MDW - JAN
MDWJAN
Chicago Midway
Tue 7/21
7:10 am-11:45 am
1 stop4h 35m
Jackson-Evers Intl
Thu 7/23
11:25 am-5:50 pm
1 stop6h 25m
$461
ChicagoJackson
ORD - JAN
ORDJAN
Chicago O'Hare Intl
Fri 7/3
4:45 pm-11:48 pm
1 stop7h 03m
Jackson-Evers Intl
Mon 7/6
7:26 pm-12:50 am
1 stop5h 24m
$472
Showing 1-10 of 29 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 June.
| 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, September is the cheapest month in which you can book a flight from Chicago to Jackson, Mississippi (average of $236). Flying from Chicago to Jackson, Mississippi in March is currently the most expensive (average of $366). 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?
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 June 24, 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.
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Entertainment
7.5
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 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
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Chicago and Jackson flights
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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 2,558,603 searches. Data last updated June 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$236 | Average$436 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$280 | Average$388 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$352 | Average$538 | FlexibilityNo cancel fee | On-time63% |