$155+ 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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAN
Oct 5 — Oct 121
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 5, 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 5, 2026.
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/1![American Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 9/2. 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 10/202:10 pm -
1 stop3h 50m
Tue 10/276:35 pm -
1 stop4h 40m
Deal found 9/2![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 9/2. 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.
Wed 11/1112:45 pm -
1 stop4h 50m
Mon 11/166:15 pm -
1 stop4h 50m
Deal found 9/2![Southwest logo]()
$318
This American Airlines deal was found by Cheapflights users on 9/2. 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.
Fri 11/61:22 pm -
1 stop5h 57m
Mon 11/95:48 pm -
1 stop6h 13m
Deal found 9/2![American Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/226:40 am -
1 stop5h 37m
Wed 9/235:14 pm -
1 stop6h 45m
Deal found 9/1![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/1![Delta logo]()
$327
This American Airlines deal was found by Cheapflights users on 9/2. 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.
Thu 10/84:45 pm -
1 stop7h 10m
Mon 10/122:36 pm -
1 stop8h 24m
Deal found 9/2![American Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/2310:15 am -
2 stops9h 35m
Mon 9/2812:40 pm -
1 stop7h 30m
Deal found 8/31![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 9/2. 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 9/295:30 am -
1 stop6h 47m
Fri 10/27:08 pm -
1 stop4h 51m
Deal found 9/2![Delta logo]()
$340
This Southwest deal was found by Cheapflights users on 9/2. 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.
Wed 9/237:50 am -
1 stop5h 00m
Thu 9/2412:40 pm -
1 stop7h 30m
Deal found 9/2![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/2211:50 am -
1 stop10h 05m
Tue 10/276:40 am -
1 stop4h 45m
Deal found 9/1![Southwest logo]()
$352
This Delta deal was found by Cheapflights users on 9/2. 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.
Thu 12/171:30 pm -
1 stop7h 20m
Wed 12/232:08 pm -
1 stop5h 51m
Deal found 9/2![Delta logo]()
$360
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 5, 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 5, 2026.
This Southwest deal was found by Cheapflights users on 9/2. 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 10/202:10 pm -
1 stop3h 50m
Tue 10/276:35 pm -
1 stop4h 40m
Deal found 9/2![Southwest logo]()
$309
This Delta deal was found by Cheapflights users on 9/2. 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 9/295:30 am -
1 stop6h 47m
Fri 10/27:08 pm -
1 stop4h 51m
Deal found 9/2![Delta logo]()
$340
This United Airlines deal was found by Cheapflights users on 9/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:30 am -
1 stop14h 28m
Tue 9/297:00 am -
2 stops13h 30m
Deal found 9/2![United Airlines logo]()
$527
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1110:55 am -
2 stops8h 55m
Mon 11/166:15 pm -
1 stop4h 50m
Deal found 9/1![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 9/2. 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.
Wed 11/186:40 am -
1 stop5h 50m
Sat 11/218:20 pm -
1 stop4h 25m
Deal found 9/2![Southwest logo]()
$318
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 12/116:00 am -
1 stop6h 44m
Sun 12/135:11 pm -
1 stop5h 44m
Deal found 8/31![Delta logo]()
$383
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/237:50 am -
1 stop5h 00m
Mon 9/2812:40 pm -
1 stop7h 30m
Deal found 8/31![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/2211:50 am -
1 stop10h 05m
Tue 10/2712:55 pm -
2 stops9h 05m
Deal found 9/1![Southwest logo]()
$358
This United Airlines deal was found by Cheapflights users on 9/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:29 am -
1 stop9h 05m
Tue 11/35:23 pm -
2 stops16h 41m
Deal found 9/3![United Airlines logo]()
$527
This United Airlines deal was found by Cheapflights users on 9/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:30 am -
1 stop11h 04m
Tue 11/105:23 pm -
2 stops13h 13m
Deal found 9/3![United Airlines logo]()
$527
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 11/610:00 pm -
2 stops15h 19m
Mon 11/95:23 pm -
2 stops17h 53m
Deal found 9/1![United Airlines logo]()
$532
This United Airlines deal was found by Cheapflights users on 9/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:50 pm -
2 stops24h 10m
Mon 10/195:20 pm -
2 stops19h 51m
Deal found 9/3![United Airlines logo]()
$550
This United Airlines deal was found by Cheapflights users on 9/5. 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.
Thu 10/299:15 am -
1 stop7h 19m
Sun 11/111:57 am -
2 stops19h 02m
Deal found 9/5![United Airlines logo]()
$593
This United Airlines deal was found by Cheapflights users on 9/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:30 am -
1 stop7h 53m
Wed 9/2312:00 pm -
1 stop6h 30m
Deal found 9/4![United Airlines logo]()
$599
Last-minute flights from Chicago to JacksonDiscover last-minute flight deals from Chicago to Jackson. Data last updated September 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Jackson. Data last updated September 5, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/226:40 am -
1 stop5h 37m
Wed 9/235:14 pm -
1 stop6h 45m
Deal found 9/1![Delta logo]()
$327
This American Airlines deal was found by Cheapflights users on 9/2. 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.
Wed 9/238:05 am -
1 stop6h 47m
Tue 9/293:27 pm -
1 stop7h 04m
Deal found 9/2![American Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/237:50 am -
1 stop5h 00m
Mon 9/2812:40 pm -
1 stop7h 30m
Deal found 8/31![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 9/2. 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.
Wed 9/237:50 am -
1 stop5h 00m
Thu 9/2412:40 pm -
1 stop7h 30m
Deal found 9/2![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/247:25 am -
1 stop4h 35m
Mon 9/2812:40 pm -
2 stops9h 20m
Deal found 9/1![Southwest logo]()
$362
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/248:05 am -
1 stop6h 12m
Fri 9/257:04 pm -
1 stop4h 55m
Deal found 9/1![Delta logo]()
$376
This Delta deal was found by Cheapflights users on 9/2. 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 9/295:30 am -
1 stop6h 47m
Fri 10/27:08 pm -
1 stop4h 51m
Deal found 9/2![Delta logo]()
$340
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Fri 10/26:00 am -
1 stop5h 47m
Fri 10/96:45 pm -
1 stop5h 23m
Deal found 9/4![American Airlines logo]()
$377
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/76:00 am -
1 stop5h 45m
Thu 10/156:45 pm -
1 stop5h 23m
Deal found 8/31![American Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 9/2. 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.
Thu 10/84:45 pm -
1 stop7h 10m
Mon 10/122:36 pm -
1 stop8h 24m
Deal found 9/2![American Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 9/2. 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 10/202:10 pm -
1 stop3h 50m
Tue 10/276:35 pm -
1 stop4h 40m
Deal found 9/2![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/2211:50 am -
1 stop10h 05m
Tue 10/276:40 am -
1 stop4h 45m
Deal found 9/1![Southwest logo]()
$352
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 5, 2026.
Search for one-way flight options from Chicago to Jackson. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
This American Airlines deal was found by Cheapflights users on 9/2. 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.
Thu 11/511:40 am -
1 stop7h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![American Airlines logo]()
$155
This Southwest deal was found by Cheapflights users on 9/2. 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 11/512:25 pm -
1 stop9h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Southwest logo]()
$160
This Delta deal was found by Cheapflights users on 9/2. 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.
Thu 12/1711:35 am -
1 stop4h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Delta logo]()
$164
This Delta deal was found by Cheapflights users on 9/2. 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.
Mon 2/16:00 am -
1 stop5h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Delta logo]()
$164
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/116:40 am -
1 stop5h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Delta logo]()
$189
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/115:25 am -
1 stop6h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Southwest logo]()
$189
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Sun 10/186:00 am -
1 stop5h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![American Airlines logo]()
$199
This Delta deal was found by Cheapflights users on 9/5. 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.
Tue 9/296:40 am -
1 stop5h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Delta logo]()
$208
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Sun 9/275:18 am -
1 stop5h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![American Airlines logo]()
$209
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Fri 9/185:00 am -
1 stop6h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![American Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 9/4. 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.
Sun 10/186:04 am -
1 stop6h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Delta logo]()
$243
This United Airlines deal was found by Cheapflights users on 9/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/19:51 pm -
2 stops13h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![United Airlines logo]()
$281
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 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $309 (American Airlines) |
One-way from | $155 (American Airlines) |
Popular in | December |
Cheapest in | August |
Average price | $512 |
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 5, 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 Chicago O'Hare Intl - JAN Jackson-Evers Intl
ORDJAN
Chicago O'Hare Intl
Thu 11/5
11:40 am-7:19 pm
1 stop7h 39m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Thu 11/5
12:25 pm-10:05 pm
1 stop9h 40m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$160
Quickest round-trip
ChicagoJackson
ORD Chicago O'Hare Intl - JAN Jackson-Evers Intl
ORDJAN
Chicago O'Hare Intl
Mon 2/1
7:10 am-11:22 am
1 stop4h 12m
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 12/17
11:35 am-4:24 pm
1 stop4h 49m
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 2/1
6:00 am-11:22 am
1 stop5h 22m
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
Mon 9/28
4:45 pm-10:52 pm
1 stop6h 07m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Mon 2/1
10:15 am-7:50 pm
2 stops9h 35m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Fri 9/11
5:25 am-12:00 pm
1 stop6h 35m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
ChicagoJackson
ORD Chicago O'Hare Intl - JAN Jackson-Evers Intl
ORDJAN
Chicago O'Hare Intl
Fri 9/11
6:40 am-11:46 am
1 stop5h 06m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
ChicagoJackson
ORD Chicago O'Hare Intl - JAN Jackson-Evers Intl
ORDJAN
Chicago O'Hare Intl
Sun 10/18
6:00 am-11:45 am
1 stop5h 45m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$199
Showing 1-10 of 31 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
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, 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 February is currently the most expensive (average of $576). 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 $321 and $617 in November.The cheapest round-trip price found within the last 5 days was $309 on American Airlines (Nov 11-Nov 16).
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 5, 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.
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
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 5, 2026.
Chicago and Jackson flights
Browse other Chicago and Jackson flight options. Last updated on September 5, 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 5, 2026.
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Top 2 airlines flying from Chicago to Jackson
Discover the top 2 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 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$270 | Average$388 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$366 | Average$488 | FlexibilityNo cancel fee | On-time71% |