$123+ Cheap flights from Jackson, MS (JAN) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Oct 17 — Oct 241
Round-trip
1 adult, Economy
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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 September 17, 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 September 17, 2026.
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/76:45 pm -
1 stop5h 23m
Wed 10/146:40 pm -
1 stop5h 15m
Deal found 9/16![American Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:02 pm -
1 stop5h 31m
Sat 10/246:04 am -
1 stop5h 45m
Deal found 9/15![Delta logo]()
$245
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1712:30 pm -
1 stop7h 30m
Sat 10/248:40 am -
1 stop6h 05m
Deal found 9/14![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/101:10 pm -
1 stop5h 55m
Thu 11/125:15 am -
1 stop5h 50m
Deal found 9/17![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:51 am -
1 stop4h 29m
Thu 11/121:30 pm -
1 stop7h 09m
Deal found 9/17![Delta logo]()
$292
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/2912:00 pm -
1 stop3h 55m
Thu 11/512:25 pm -
1 stop9h 45m
Deal found 9/14![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/255:06 pm -
1 stop5h 48m
Wed 12/306:00 am -
1 stop5h 11m
Deal found 9/14![Delta logo]()
$311
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:14 pm -
1 stop5h 30m
Thu 10/86:04 am -
1 stop6h 10m
Deal found 9/17![Delta logo]()
$315
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/284:46 pm -
1 stop7h 13m
Sun 11/15:19 am -
1 stop5h 03m
Deal found 9/14![American Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 12/302:08 pm -
1 stop5h 51m
Sat 1/26:40 am -
1 stop6h 43m
Deal found 9/14![Delta logo]()
$331
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 12/136:34 pm -
1 stop5h 27m
Thu 1/76:00 am -
1 stop5h 44m
Deal found 9/15![American Airlines logo]()
$338
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/207:30 pm -
1 stop4h 24m
Mon 11/235:30 am -
1 stop4h 59m
Deal found 9/14![Delta 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 September 17, 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 September 17, 2026.
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:02 pm -
1 stop5h 31m
Sat 10/246:04 am -
1 stop5h 45m
Deal found 9/15![Delta logo]()
$245
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1712:30 pm -
1 stop7h 30m
Sat 10/248:40 am -
1 stop6h 05m
Deal found 9/14![Southwest logo]()
$246
This American Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/212:17 pm -
1 stop8h 13m
Mon 10/54:45 pm -
1 stop7h 10m
Deal found 9/13![American Airlines logo]()
$447
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/101:10 pm -
1 stop5h 55m
Thu 11/125:15 am -
1 stop5h 50m
Deal found 9/17![Southwest logo]()
$269
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/177:00 am -
1 stop11h 30m
Sat 10/248:40 am -
2 stops11h 20m
Deal found 9/15![United Airlines logo]()
$557
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 1/1312:10 pm -
1 stop6h 22m
Wed 5/55:30 am -
1 stop4h 35m
Deal found 9/16![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/2912:00 pm -
2 stops7h 55m
Thu 11/512:25 pm -
1 stop9h 45m
Deal found 9/14![Southwest logo]()
$304
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:14 pm -
1 stop5h 30m
Thu 10/86:04 am -
1 stop6h 10m
Deal found 9/17![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:40 am -
1 stop4h 40m
Thu 1/712:25 pm -
2 stops7h 25m
Deal found 9/15![Southwest logo]()
$350
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/173:33 pm -
1 stop5h 05m
Sat 10/2410:35 am -
1 stop4h 03m
Deal found 9/14![Delta logo]()
$376
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 12/96:15 pm -
1 stop4h 50m
Sun 12/135:15 am -
1 stop5h 50m
Deal found 9/13![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:45 am -
1 stop6h 43m
Thu 11/56:30 am -
1 stop5h 19m
Deal found 9/14![Delta logo]()
$397
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:50 am -
2 stops13h 18m
Thu 11/125:30 am -
1 stop5h 45m
Deal found 9/17![United Airlines logo]()
$562
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 2/21:57 pm -
1 stop9h 02m
Wed 2/38:40 am -
2 stops12h 38m
Deal found 9/16![United Airlines logo]()
$569
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/77:00 am -
2 stops11h 35m
Sun 10/116:25 am -
1 stop5h 02m
Deal found 9/14![United Airlines logo]()
$574
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 12/911:58 am -
2 stops18h 31m
Sun 12/135:45 am -
1 stop5h 38m
Deal found 9/13![United Airlines logo]()
$591
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:20 pm -
1 stop6h 06m
Tue 10/67:30 am -
2 stops12h 30m
Deal found 9/17![United Airlines logo]()
$596
Last-minute flights from Jackson to ChicagoDiscover last-minute flight deals from Jackson to Chicago. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chicago. Data last updated September 17, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:02 pm -
1 stop5h 54m
Wed 10/75:27 am -
1 stop4h 58m
Deal found 9/15![Delta logo]()
$371
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:14 pm -
1 stop5h 30m
Wed 10/76:04 am -
1 stop4h 21m
Deal found 9/15![Delta logo]()
$371
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/76:45 pm -
1 stop5h 23m
Wed 10/146:40 pm -
1 stop5h 15m
Deal found 9/16![American Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:02 pm -
1 stop6h 55m
Sun 10/115:27 am -
1 stop6h 47m
Deal found 9/14![Delta logo]()
$362
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:02 pm -
1 stop5h 31m
Sun 10/116:04 am -
1 stop4h 21m
Deal found 9/14![Delta logo]()
$362
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/164:46 pm -
1 stop7h 13m
Mon 10/196:40 pm -
1 stop5h 15m
Deal found 9/16![American Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:02 pm -
1 stop5h 31m
Sat 10/246:04 am -
1 stop5h 45m
Deal found 9/15![Delta logo]()
$245
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1712:30 pm -
1 stop7h 30m
Sat 10/248:40 am -
1 stop6h 05m
Deal found 9/14![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/173:33 pm -
1 stop5h 05m
Sat 10/2410:35 am -
1 stop4h 03m
Deal found 9/14![Delta logo]()
$376
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/284:46 pm -
1 stop7h 13m
Sun 11/15:19 am -
1 stop5h 03m
Deal found 9/14![American Airlines logo]()
$321
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/2912:00 pm -
1 stop3h 55m
Thu 11/512:25 pm -
1 stop9h 45m
Deal found 9/14![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:45 am -
1 stop6h 43m
Thu 11/56:30 am -
1 stop5h 19m
Deal found 9/14![Delta logo]()
$397
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 September 17, 2026.
Search for one-way flight options from Jackson to Chicago. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:02 pm -
1 stop6h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$123
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/289:18 am -
1 stop6h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$123
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2812:55 pm -
2 stops9h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/712:55 pm -
1 stop9h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$141
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/2912:00 pm -
1 stop3h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$147
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:00 am -
1 stop8h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![American Airlines logo]()
$189
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:23 am -
1 stop6h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![American Airlines logo]()
$198
This American Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:45 pm -
1 stop5h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![American Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/103:20 pm -
1 stop6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Southwest logo]()
$199
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/96:45 pm -
1 stop5h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/48:25 pm -
1 stop4h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Southwest logo]()
$209
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:14 pm -
1 stop5h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![American Airlines logo]()
$249
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 September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $245 (American Airlines) |
One-way from | $123 (Delta) |
Popular in | June |
Cheapest in | April |
Average price | $470 |
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 September 17, 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
Wed 10/7
12:55 pm-10:15 pm
1 stop9h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$141
Quickest round-trip
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Thu 10/29
12:00 pm-3:55 pm
1 stop3h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$147
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Mon 10/12
5:55 am-3:05 pm
2 stops9h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$204
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Mon 10/12
3:33 pm-10:33 pm
1 stop7h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$209
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Sat 10/17
5:02 pm-10:33 pm
1 stop5h 31m
Chicago Midway
Sat 10/24
6:04 am-11:49 am
1 stop5h 45m
$245
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Sat 10/17
12:30 pm-8:00 pm
1 stop7h 30m
Chicago Midway
Sat 10/24
8:40 am-2:45 pm
1 stop6h 05m
$246
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Tue 11/10
1:10 pm-7:05 pm
1 stop5h 55m
Chicago Midway
Thu 11/12
5:15 am-11:05 am
1 stop5h 50m
$269
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Tue 9/22
9:20 am-2:51 pm
1 stop5h 31m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$282
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Tue 9/22
1:03 pm-6:45 pm
1 stop5h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$282
JacksonChicago
JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl
JANORD
Jackson-Evers Intl
Wed 9/23
5:20 pm-11:27 pm
1 stop6h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$282
Showing 1-10 of 32 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 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 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, January is the cheapest month in which you can book a flight from Jackson, Mississippi to Chicago (average of $345). 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 September 17, 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
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
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
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Jackson and Chicago flights
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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 September 17, 2026.
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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 September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$254 | Average$406 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$296 | Average$530 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$308 | Average$428 | FlexibilityNo cancel fee | On-time63% |