$155+ Cheap flights from Jackson, MS (JAN) to Chicago (CHI)
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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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Find cheap flights from Jackson to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Jackson to ChicagoExplore the most affordable flight options available from Jackson to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
Explore the most affordable flight options available from Jackson to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1511:08 am -
1 stop7h 37m
Tue 9/226:40 am -
1 stop5h 37m
Deal found 8/18![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:05 am -
1 stop5h 10m
Thu 9/175:25 am -
1 stop6h 35m
Deal found 8/17![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/151:30 pm -
2 stops8h 25m
Tue 9/227:50 am -
1 stop5h 00m
Deal found 8/17![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 8/21. 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 11/58:15 pm -
1 stop4h 50m
Mon 11/95:15 am -
1 stop5h 50m
Deal found 8/21![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:30 pm -
2 stops8h 25m
Wed 9/236:00 am -
2 stops6h 50m
Deal found 8/18![Southwest logo]()
$319
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals ”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:04 pm -
1 stop4h 55m
Mon 9/285:30 am -
1 stop6h 47m
Deal found 8/18![Delta logo]()
$322
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:12 pm -
1 stop5h 32m
Mon 9/286:05 am -
1 stop6h 12m
Deal found 8/18![Delta logo]()
$322
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:02 pm -
1 stop5h 54m
Thu 9/175:30 am -
1 stop4h 53m
Deal found 8/17![Delta logo]()
$327
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/174:33 pm -
1 stop6h 57m
Tue 10/136:00 am -
1 stop5h 45m
Deal found 8/17![American Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1812:40 pm -
1 stop9h 45m
Sat 9/261:45 pm -
1 stop5h 25m
Deal found 8/20![Southwest logo]()
$336
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:03 pm -
1 stop6h 56m
Fri 9/116:40 am -
1 stop5h 06m
Deal found 8/17![Delta logo]()
$340
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:40 pm -
1 stop4h 35m
Fri 9/1112:30 pm -
2 stops7h 45m
Deal found 8/17![Southwest logo]()
$348
Best flights from Jackson to ChicagoDiscover carefully curated flight deals from Jackson to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
Discover carefully curated flight deals from Jackson to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
This Delta deal was found by Cheapflights users on 8/20. 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 9/265:14 pm -
1 stop5h 30m
Wed 9/306:05 am -
1 stop4h 18m
Deal found 8/20![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 8/20. 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 9/262:30 pm -
1 stop4h 50m
Wed 9/3010:15 am -
2 stops9h 35m
Deal found 8/20![Southwest logo]()
$314
This United Airlines deal was found by Cheapflights users on 8/19. 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.
Tue 2/27:00 am -
1 stop14h 11m
Wed 2/39:30 pm -
1 stop13h 43m
Deal found 8/19![United Airlines logo]()
$465
This American Airlines deal was found by Cheapflights users on 8/21. 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.
Thu 10/82:36 pm -
1 stop8h 24m
Sun 10/116:00 am -
1 stop5h 45m
Deal found 8/21![American Airlines logo]()
$483
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:30 pm -
2 stops8h 25m
Wed 9/236:00 am -
2 stops6h 50m
Deal found 8/18![Southwest logo]()
$319
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:04 pm -
1 stop4h 55m
Mon 9/285:30 am -
1 stop6h 47m
Deal found 8/17![Delta logo]()
$322
This Delta deal was found by Cheapflights users on 8/21. 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 10/233:33 pm -
1 stop7h 00m
Mon 10/2612:49 pm -
1 stop5h 55m
Deal found 8/21![Delta logo]()
$322
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:40 pm -
1 stop4h 35m
Fri 9/117:25 am -
1 stop4h 35m
Deal found 8/17![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:12 pm -
1 stop5h 32m
Mon 9/286:05 am -
1 stop6h 12m
Deal found 8/17![Delta logo]()
$322
This Southwest deal was found by Cheapflights users on 8/21. 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 11/58:15 pm -
1 stop4h 50m
Mon 11/911:10 am -
2 stops8h 35m
Deal found 8/21![Southwest logo]()
$323
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:02 pm -
1 stop5h 54m
Thu 9/175:30 am -
1 stop4h 53m
Deal found 8/17![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1812:40 pm -
1 stop9h 45m
Sat 9/261:45 pm -
1 stop5h 25m
Deal found 8/20![Southwest logo]()
$336
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:03 pm -
1 stop6h 56m
Fri 9/116:40 am -
1 stop5h 06m
Deal found 8/17![Delta logo]()
$340
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/151:30 pm -
2 stops8h 25m
Thu 9/175:30 am -
2 stops6h 30m
Deal found 8/17![Southwest logo]()
$342
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:20 am -
2 stops11h 10m
Mon 9/286:25 am -
1 stop13h 35m
Deal found 8/18![United Airlines logo]()
$527
This United Airlines deal was found by Cheapflights users on 8/19. 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 9/162:05 pm -
1 stop10h 54m
Wed 9/239:22 am -
2 stops12h 36m
Deal found 8/19![United Airlines logo]()
$527
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:49 am -
1 stop6h 20m
Sun 9/65:30 am -
1 stop4h 13m
Deal found 8/18![Delta logo]()
$361
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:00 am -
2 stops11h 30m
Mon 9/149:35 pm -
1 stop13h 40m
Deal found 8/21![United Airlines logo]()
$527
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:20 am -
1 stop12h 22m
Sat 10/39:30 pm -
2 stops13h 57m
Deal found 8/18![United Airlines logo]()
$529
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:03 pm -
1 stop6h 56m
Thu 9/101:51 pm -
1 stop5h 58m
Deal found 8/20![Delta logo]()
$408
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:00 am -
2 stops13h 30m
Thu 9/176:30 am -
1 stop13h 50m
Deal found 8/17![United Airlines logo]()
$564
Last-minute flights from Jackson to ChicagoDiscover last-minute flight deals from Jackson to Chicago. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chicago. Data last updated August 21, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:03 pm -
1 stop6h 56m
Fri 9/116:40 am -
1 stop5h 06m
Deal found 8/17![Delta logo]()
$340
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:40 pm -
1 stop4h 35m
Fri 9/1112:30 pm -
2 stops7h 45m
Deal found 8/17![Southwest logo]()
$348
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1511:08 am -
1 stop7h 37m
Tue 9/226:40 am -
1 stop5h 37m
Deal found 8/18![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:05 am -
1 stop5h 10m
Thu 9/175:25 am -
1 stop6h 35m
Deal found 8/17![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/151:30 pm -
2 stops8h 25m
Tue 9/227:50 am -
1 stop5h 00m
Deal found 8/17![Southwest logo]()
$314
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:02 pm -
1 stop5h 54m
Thu 9/175:30 am -
1 stop4h 53m
Deal found 8/17![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:30 pm -
2 stops8h 25m
Wed 9/236:00 am -
2 stops6h 50m
Deal found 8/18![Southwest logo]()
$319
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/174:33 pm -
1 stop6h 57m
Tue 10/136:00 am -
1 stop5h 45m
Deal found 8/17![American Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1812:40 pm -
1 stop9h 45m
Sat 9/261:45 pm -
1 stop5h 25m
Deal found 8/20![Southwest logo]()
$336
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:04 pm -
1 stop4h 55m
Mon 9/285:30 am -
1 stop6h 47m
Deal found 8/18![Delta logo]()
$322
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:12 pm -
1 stop5h 32m
Mon 9/286:05 am -
1 stop6h 12m
Deal found 8/18![Delta logo]()
$322
This American Airlines deal was found by Cheapflights users on 8/21. 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.
Wed 9/3012:14 pm -
1 stop7h 24m
Sun 10/46:30 pm -
1 stop5h 20m
Deal found 8/21![American Airlines logo]()
$353
One-way flights from Jackson to ChicagoSearch for one-way flight options from Jackson to Chicago. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
Search for one-way flight options from Jackson to Chicago. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:22 pm -
1 stop8h 08m
Deal found 8/17![American Airlines logo]()
$155
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:05 am -
1 stop7h 10m
Deal found 8/18![Southwest logo]()
$155
This Southwest deal was found by Cheapflights users on 8/20. 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.
Mon 9/2812:40 pm -
1 stop7h 30m
Deal found 8/20![Southwest logo]()
$160
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:01 pm -
1 stop6h 56m
Deal found 8/18![Delta logo]()
$161
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:32 am -
1 stop4h 27m
Deal found 8/18![Delta logo]()
$161
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1511:08 am -
1 stop7h 37m
Deal found 8/18![Delta logo]()
$164
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:03 pm -
1 stop5h 41m
Deal found 8/18![Delta logo]()
$164
This Delta deal was found by Cheapflights users on 8/21. 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 1/156:59 pm -
1 stop4h 51m
Deal found 8/21![Delta logo]()
$168
This Delta deal was found by Cheapflights users on 8/21. 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 1/155:35 pm -
1 stop4h 35m
Deal found 8/21![Delta logo]()
$168
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:40 pm -
2 stops6h 50m
Deal found 8/18![Southwest logo]()
$169
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:14 pm -
1 stop6h 45m
Deal found 8/17![Delta logo]()
$177
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:03 pm -
1 stop5h 41m
Deal found 8/18![Delta logo]()
$177
Find flight deals from Jackson to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Jackson (JAN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $309 (Delta) |
One-way from | $155 (American Airlines) |
Popular in | June |
Cheapest in | April |
Average price | $354 |
Cheapflights Fare Finder
Customize your flight search to find flights from Jackson to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 21, 2026.
Use the filters below to find and compare flights from Jackson to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Sat 9/26
5:14 pm-10:44 pm
1 stop5h 30m
Chicago Midway
Wed 9/30
6:05 am-10:23 am
1 stop4h 18m
$309
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Sat 9/26
2:30 pm-7:20 pm
1 stop4h 50m
Chicago Midway
Wed 9/30
10:15 am-7:50 pm
2 stops9h 35m
$314
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Wed 9/16
1:30 pm-9:55 pm
2 stops8h 25m
Chicago Midway
Wed 9/23
6:00 am-12:50 pm
2 stops6h 50m
$319
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Fri 9/25
7:04 pm-11:59 pm
1 stop4h 55m
Chicago O'Hare Intl
Mon 9/28
5:30 am-12:17 pm
1 stop6h 47m
$322
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Fri 10/23
3:33 pm-10:33 pm
1 stop7h 00m
Chicago Midway
Mon 10/26
12:49 pm-6:44 pm
1 stop5h 55m
$322
Quickest round-trip
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Tue 9/8
6:40 pm-11:15 pm
1 stop4h 35m
Chicago Midway
Fri 9/11
7:25 am-12:00 pm
1 stop4h 35m
$322
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Fri 9/25
5:12 pm-10:44 pm
1 stop5h 32m
Chicago Midway
Mon 9/28
6:05 am-12:17 pm
1 stop6h 12m
$322
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Thu 11/5
8:15 pm-1:05 am
1 stop4h 50m
Chicago Midway
Mon 11/9
11:10 am-7:45 pm
2 stops8h 35m
$323
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Tue 9/15
3:02 pm-8:56 pm
1 stop5h 54m
Chicago O'Hare Intl
Thu 9/17
5:30 am-10:23 am
1 stop4h 53m
$327
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Fri 9/18
12:40 pm-10:25 pm
1 stop9h 45m
Chicago Midway
Sat 9/26
1:45 pm-7:10 pm
1 stop5h 25m
$336
Showing 1-10 of 39 resultsSorted by cheapest first
Compare providers for flights from Jackson to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Jackson to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Jackson, Mississippi-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jackson, Mississippi-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Jackson, Mississippi-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Jackson, Mississippi-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Jackson, Mississippi-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Jackson to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Jackson with our price prediction graph.
JAN-CHI
JAN-ORD
JAN-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Jackson to Chicago
JAN-CHI
JAN-ORD
JAN-MDW
What is the cheapest month to book a flight from Jackson, Mississippi to Chicago?
Currently, October is the cheapest month in which you can book a flight from Jackson, Mississippi to Chicago (average of $321). Flying from Jackson, Mississippi to Chicago in June is currently the most expensive (average of $674). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 21, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andAmerican Airlines from Jackson to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Jackson to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 21, 2026.
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Jackson and Chicago flights
Browse other Jackson and Chicago flight options. Last updated on August 21, 2026.
Other flights from Jackson
Browse through other flights departing from Jackson. Flights are based on user searches made on Cheapflights and were last updated on August 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Jackson to Chicago
Discover the top 3 airlines that operate flights from Jackson to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$249 | Average$386 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$296 | Average$519 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$308 | Average$426 | FlexibilityNo cancel fee | On-time63% |