$160+ 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 6/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAN
Jun 6 — Jun 131
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Jackson with Cheapflights
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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 May 7, 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 May 7, 2026.
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:50 pm
ORD
- JAN
1 stop6h 30m
American Airlines
Tue 5/267:29 pm
JAN
- ORD
1 stop5h 13m
American Airlines
Deal found 5/2![American Airlines logo]()
$333
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:23 am
MDW
- JAN
1 stop5h 49m
Delta
Tue 5/2610:51 am
JAN
- MDW
1 stop5h 21m
Delta
Deal found 5/2![Delta logo]()
$333
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/105:34 pm
ORD
- JAN
1 stop6h 20m
American Airlines
Tue 6/165:29 pm
JAN
- ORD
1 stop6h 03m
American Airlines
Deal found 5/6![American Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/103:10 pm
MDW
- JAN
1 stop3h 35m
Southwest
Tue 6/167:15 pm
JAN
- MDW
1 stop4h 35m
Southwest
Deal found 5/6![Southwest logo]()
$339
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/287:58 am
ORD
- JAN
1 stop7h 53m
American Airlines
Wed 6/37:29 pm
JAN
- ORD
1 stop5h 13m
American Airlines
Deal found 5/7![American Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 9/191:45 pm
MDW
- JAN
1 stop5h 20m
Southwest
Tue 9/227:05 am
JAN
- MDW
1 stop5h 10m
Southwest
Deal found 5/6![Southwest logo]()
$343
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:48 am
ORD
- JAN
1 stop7h 03m
American Airlines
Mon 5/257:29 pm
JAN
- ORD
1 stop5h 13m
American Airlines
Deal found 5/2![American Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:23 am
MDW
- JAN
1 stop5h 49m
Delta
Mon 6/85:04 pm
JAN
- MDW
1 stop5h 13m
Delta
Deal found 5/4![Delta logo]()
$347
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/309:10 am
ORD
- JAN
1 stop7h 06m
Delta
Wed 6/312:59 pm
JAN
- ORD
1 stop7h 27m
Delta
Deal found 5/7![Delta logo]()
$353
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/2810:59 am
MDW
- JAN
1 stop5h 16m
Delta
Wed 6/35:05 pm
JAN
- MDW
1 stop4h 04m
Delta
Deal found 5/7![Delta logo]()
$353
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/285:30 am
ORD
- JAN
1 stop6h 42m
Delta
Mon 6/17:23 pm
JAN
- ORD
1 stop4h 36m
Delta
Deal found 5/7![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/2810:59 am
MDW
- JAN
1 stop5h 16m
Delta
Thu 6/42:55 pm
JAN
- MDW
1 stop6h 14m
Delta
Deal found 5/7![Delta logo]()
$357
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 May 7, 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 May 7, 2026.
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/35:30 am
ORD
- JAN
1 stop4h 34m
Delta
Wed 6/105:04 pm
JAN
- ORD
1 stop6h 55m
Delta
Deal found 5/6![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/103:10 pm
MDW
- JAN
1 stop3h 35m
Southwest
Tue 6/167:15 pm
JAN
- MDW
1 stop4h 35m
Southwest
Deal found 5/6![Southwest logo]()
$339
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/226:35 am
ORD
- JAN
1 stop5h 30m
Delta
Sun 7/267:10 pm
JAN
- ORD
1 stop4h 43m
Delta
Deal found 5/5![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 7/3011:00 am
MDW
- JAN
2 stops8h 45m
Southwest
Sun 8/25:30 am
JAN
- MDW
2 stops9h 00m
Southwest
Deal found 5/3![Southwest logo]()
$397
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/226:00 am
MDW
- JAN
1 stop6h 05m
Delta
Sun 7/269:15 am
JAN
- MDW
1 stop7h 00m
Delta
Deal found 5/5![Delta logo]()
$373
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:23 am
MDW
- JAN
1 stop5h 49m
Delta
Mon 6/85:04 pm
JAN
- MDW
1 stop5h 13m
Delta
Deal found 5/4![Delta logo]()
$373
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/311:00 am
MDW
- JAN
2 stops8h 45m
Southwest
Fri 7/105:10 am
JAN
- MDW
1 stop5h 30m
Southwest
Deal found 5/5![Southwest logo]()
$412
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/2510:10 am
MDW
- JAN
1 stop11h 45m
Southwest
Mon 6/2911:25 am
JAN
- MDW
1 stop6h 25m
Southwest
Deal found 5/5![Southwest logo]()
$412
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 7/35:30 am
ORD
- JAN
1 stop6h 40m
Delta
Sun 7/512:57 pm
JAN
- ORD
1 stop5h 45m
Delta
Deal found 5/4![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/11:10 pm
MDW
- JAN
2 stops7h 50m
Southwest
Mon 6/85:10 am
JAN
- MDW
2 stops8h 35m
Southwest
Deal found 5/4![Southwest logo]()
$425
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 7/311:05 am
MDW
- JAN
1 stop7h 10m
Delta
Sun 7/59:12 am
JAN
- MDW
1 stop7h 14m
Delta
Deal found 5/3![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/222:40 pm
ORD
- JAN
1 stop4h 25m
Southwest
Sun 5/246:00 pm
JAN
- ORD
2 stops15h 45m
Southwest
Deal found 5/6![Southwest logo]()
$438
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:23 am
MDW
- JAN
1 stop5h 49m
Delta
Mon 5/2510:51 am
JAN
- MDW
1 stop5h 21m
Delta
Deal found 5/2![Delta logo]()
$413
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/217:20 pm
ORD
- JAN
2 stops16h 20m
Southwest
Sun 5/246:00 pm
JAN
- ORD
2 stops15h 45m
Southwest
Deal found 5/2![Southwest logo]()
$470
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/222:40 pm
ORD
- JAN
1 stop4h 25m
Southwest
Sat 5/236:00 am
JAN
- ORD
2 stops15h 55m
Southwest
Deal found 5/2![Southwest logo]()
$514
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/1911:55 am
ORD
- JAN
2 stops8h 25m
Southwest
Sat 5/2312:20 pm
JAN
- ORD
2 stops9h 35m
Southwest
Deal found 5/4![Southwest logo]()
$523
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/217:20 pm
ORD
- JAN
2 stops16h 20m
Southwest
Sat 5/2312:20 pm
JAN
- ORD
2 stops9h 35m
Southwest
Deal found 5/3![Southwest logo]()
$540
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/212:40 pm
ORD
- JAN
1 stop4h 25m
Southwest
Mon 5/255:45 am
JAN
- ORD
2 stops9h 45m
Southwest
Deal found 5/5![Southwest logo]()
$564
Last-minute flights from Chicago to JacksonDiscover last-minute flight deals from Chicago to Jackson. Data last updated May 7, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Jackson. Data last updated May 7, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:50 pm
ORD
- JAN
1 stop6h 30m
American Airlines
Tue 5/267:29 pm
JAN
- ORD
1 stop5h 13m
American Airlines
Deal found 5/2![American Airlines logo]()
$333
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:23 am
MDW
- JAN
1 stop5h 49m
Delta
Tue 5/2610:51 am
JAN
- MDW
1 stop5h 21m
Delta
Deal found 5/2![Delta logo]()
$333
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:48 am
ORD
- JAN
1 stop7h 03m
American Airlines
Mon 5/257:29 pm
JAN
- ORD
1 stop5h 13m
American Airlines
Deal found 5/2![American Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/2711:55 am
ORD
- JAN
2 stops8h 25m
Southwest
Thu 5/285:45 am
JAN
- ORD
2 stops9h 45m
Southwest
Deal found 5/4![Southwest logo]()
$363
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/287:58 am
ORD
- JAN
1 stop7h 53m
American Airlines
Wed 6/37:29 pm
JAN
- ORD
1 stop5h 13m
American Airlines
Deal found 5/7![American Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/2810:59 am
MDW
- JAN
1 stop5h 16m
Delta
Wed 6/35:05 pm
JAN
- MDW
1 stop4h 04m
Delta
Deal found 5/7![Delta logo]()
$353
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/285:30 am
ORD
- JAN
1 stop6h 42m
Delta
Mon 6/17:23 pm
JAN
- ORD
1 stop4h 36m
Delta
Deal found 5/7![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/2810:59 am
MDW
- JAN
1 stop5h 16m
Delta
Thu 6/42:55 pm
JAN
- MDW
1 stop6h 14m
Delta
Deal found 5/7![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/309:10 am
ORD
- JAN
1 stop7h 06m
Delta
Wed 6/312:59 pm
JAN
- ORD
1 stop7h 27m
Delta
Deal found 5/7![Delta logo]()
$353
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:23 am
MDW
- JAN
1 stop5h 49m
Delta
Mon 6/85:04 pm
JAN
- MDW
1 stop5h 13m
Delta
Deal found 5/4![Delta logo]()
$347
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/105:10 am
ORD
- JAN
1 stop5h 16m
American Airlines
Tue 6/165:24 am
JAN
- ORD
1 stop5h 44m
American Airlines
Deal found 5/5![American Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/103:10 pm
MDW
- JAN
1 stop3h 35m
Southwest
Tue 6/167:15 pm
JAN
- MDW
1 stop4h 35m
Southwest
Deal found 5/6![Southwest logo]()
$339
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 May 7, 2026.
Search for one-way flight options from Chicago to Jackson. Find affordable one-way fares based on user searches. Data last updated May 7, 2026.
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:00 am
MDW
- JAN
1 stop4h 08m
Delta
Deal found 5/2![Delta logo]()
$160
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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
Deal found 5/5![Southwest logo]()
$170
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/1611:25 am
MDW
- JAN
2 stops7h 20m
Southwest
Deal found 5/2![Southwest logo]()
$185
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/273:50 pm
ORD
- JAN
1 stop6h 30m
American Airlines
Deal found 5/4![American Airlines logo]()
$194
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1210:10 am
MDW
- JAN
1 stop11h 45m
Southwest
Deal found 5/4![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/278:00 am
MDW
- JAN
2 stops10h 35m
Southwest
Deal found 5/4![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/273:00 pm
MDW
- JAN
1 stop6h 55m
Southwest
Deal found 5/5![Southwest logo]()
$214
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/185:59 am
ORD
- JAN
1 stop5h 55m
American Airlines
Deal found 5/4![American Airlines logo]()
$218
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/226:47 pm
ORD
- JAN
1 stop5h 07m
American Airlines
Deal found 5/7![American Airlines logo]()
$234
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2212:53 pm
MDW
- JAN
1 stop5h 45m
Delta
Deal found 5/7![Delta logo]()
$234
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/1811:35 am
MDW
- JAN
1 stop10h 20m
Southwest
Deal found 5/4![Southwest logo]()
$239
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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.
Mon 7/279:40 pm
ORD
- JAN
1 stop13h 44m
United Airlines
Deal found 5/5![United Airlines logo]()
$283
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 May 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $333 (American Airlines) |
One-way from | $160 (Delta) |
Popular in | December |
Cheapest in | June |
Average price | $456 |
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 May 7, 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
Wed 6/3
5:30 am-10:04 am
1 stop4h 34m
Jackson-Evers Intl
Wed 6/10
5:04 pm-11:59 pm
1 stop6h 55m
$339
Quickest round-trip
ChicagoJackson
MDW - JAN
MDWJAN
Chicago Midway
Wed 6/10
3:10 pm-6:45 pm
1 stop3h 35m
Jackson-Evers Intl
Tue 6/16
7:15 pm-11:50 pm
1 stop4h 35m
$339
ChicagoJackson
ORD - JAN
ORDJAN
Chicago O'Hare Intl
Wed 7/22
6:35 am-12:05 pm
1 stop5h 30m
Jackson-Evers Intl
Sun 7/26
7:10 pm-11:53 pm
1 stop4h 43m
$363
ChicagoJackson
MDW - JAN
MDWJAN
Chicago Midway
Wed 7/22
6:00 am-12:05 pm
1 stop6h 05m
Jackson-Evers Intl
Sun 7/26
9:15 am-4:15 pm
1 stop7h 00m
$373
ChicagoJackson
MDW - JAN
MDWJAN
Chicago Midway
Mon 6/1
6:23 am-12:12 pm
1 stop5h 49m
Jackson-Evers Intl
Mon 6/8
5:04 pm-10:17 pm
1 stop5h 13m
$373
ChicagoJackson
ORD - JAN
ORDJAN
Chicago O'Hare Intl
Fri 7/3
5:30 am-12:10 pm
1 stop6h 40m
Jackson-Evers Intl
Sun 7/5
12:57 pm-6:42 pm
1 stop5h 45m
$387
ChicagoJackson
MDW - JAN
MDWJAN
Chicago Midway
Fri 7/3
11:05 am-6:15 pm
1 stop7h 10m
Jackson-Evers Intl
Sun 7/5
9:12 am-4:26 pm
1 stop7h 14m
$387
ChicagoJackson
MDW - JAN
MDWJAN
Chicago Midway
Thu 7/30
11:00 am-7:45 pm
2 stops8h 45m
Jackson-Evers Intl
Sun 8/2
5:30 am-2:30 pm
2 stops9h 00m
$397
ChicagoJackson
MDW - JAN
MDWJAN
Chicago Midway
Fri 7/3
11:00 am-7:45 pm
2 stops8h 45m
Jackson-Evers Intl
Fri 7/10
5:10 am-10:40 am
1 stop5h 30m
$412
ChicagoJackson
MDW - JAN
MDWJAN
Chicago Midway
Thu 6/25
10:10 am-9:55 pm
1 stop11h 45m
Jackson-Evers Intl
Mon 6/29
11:25 am-5:50 pm
1 stop6h 25m
$412
Showing 1-10 of 39 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 May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on 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
MDW-JAN
ORD-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
MDW-JAN
ORD-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 May 7, 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.
Overall
7.9
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from 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
Clinton
Flowood
Pearl
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Other flights to Jackson
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Chicago and Jackson flights
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Check out other popular destinations found by fellow travelers in 2026
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 May 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$236 | Average$413 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$280 | Average$447 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$352 | Average$538 | FlexibilityNo cancel fee | On-time63% |