$152+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Aug 20 — Aug 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 July 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 July 21, 2026.
This Delta deal was found by Cheapflights users on 7/20. 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.
Wed 8/195:01 pm
JAN
- ORD
1 stop6h 56m
Delta
Wed 8/265:30 am
ORD
- JAN
1 stop5h 07m
Delta
Deal found 7/20![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 7/20. 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.
Wed 8/121:30 pm
JAN
- MDW
1 stop6h 40m
Southwest
Sat 8/151:45 pm
MDW
- JAN
1 stop5h 20m
Southwest
Deal found 7/20![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 7/20. 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.
Wed 8/197:05 am
JAN
- MDW
2 stops8h 55m
Southwest
Wed 8/2611:10 am
MDW
- JAN
2 stops8h 35m
Southwest
Deal found 7/20![Southwest logo]()
$313
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:28 pm
JAN
- ORD
1 stop6h 50m
American Airlines
Sat 8/225:00 am
ORD
- JAN
1 stop6h 50m
American Airlines
Deal found 7/19![American Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 7/17. 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 9/115:03 pm
JAN
- MDW
1 stop5h 42m
Delta
Mon 9/145:11 pm
MDW
- JAN
1 stop6h 10m
Delta
Deal found 7/17![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 7/20. 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.
Wed 9/21:30 pm
JAN
- MDW
1 stop3h 25m
Southwest
Wed 9/911:10 am
MDW
- JAN
2 stops8h 35m
Southwest
Deal found 7/20![Southwest logo]()
$319
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/284:46 pm
JAN
- ORD
1 stop7h 13m
American Airlines
Sat 10/314:53 pm
ORD
- JAN
1 stop6h 02m
American Airlines
Deal found 7/19![American Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 7/18. 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
JAN
- MDW
1 stop4h 15m
Southwest
Mon 9/145:25 am
MDW
- JAN
1 stop6h 35m
Southwest
Deal found 7/18![Southwest logo]()
$325
This Southwest deal was found by Cheapflights users on 7/17. 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.
Thu 8/612:40 pm
JAN
- MDW
1 stop4h 15m
Southwest
Wed 8/122:40 pm
MDW
- JAN
1 stop3h 25m
Southwest
Deal found 7/17![Southwest logo]()
$335
This American Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:28 pm
JAN
- ORD
1 stop6h 02m
American Airlines
Mon 8/244:57 pm
ORD
- JAN
1 stop6h 02m
American Airlines
Deal found 7/21![American Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 7/16. 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.
Thu 8/205:01 pm
JAN
- MDW
1 stop5h 35m
Delta
Sat 8/226:11 am
MDW
- JAN
1 stop5h 48m
Delta
Deal found 7/16![Delta logo]()
$345
This Delta deal was found by Cheapflights users on 7/18. 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.
Thu 9/105:03 pm
JAN
- ORD
1 stop6h 56m
Delta
Mon 9/143:40 pm
ORD
- JAN
1 stop4h 55m
Delta
Deal found 7/18![Delta logo]()
$346
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 July 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 July 21, 2026.
This Southwest deal was found by Cheapflights users on 7/20. 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.
Wed 8/121:30 pm
JAN
- MDW
1 stop6h 40m
Southwest
Sat 8/151:45 pm
MDW
- JAN
1 stop5h 20m
Southwest
Deal found 7/20![Southwest logo]()
$303
This Delta deal was found by Cheapflights users on 7/16. 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.
Fri 9/115:03 pm
JAN
- MDW
1 stop5h 42m
Delta
Mon 9/146:05 am
MDW
- JAN
1 stop4h 18m
Delta
Deal found 7/16![Delta logo]()
$303
This United Airlines deal was found by Cheapflights users on 7/16. 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.
Sat 10/3112:00 pm
JAN
- ORD
1 stop12h 34m
United Airlines
Tue 11/37:40 am
ORD
- JAN
1 stop11h 48m
United Airlines
Deal found 7/16![United Airlines logo]()
$465
This Southwest deal was found by Cheapflights users on 7/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:40 pm
JAN
- MDW
2 stops6h 50m
Southwest
Mon 9/145:25 am
MDW
- JAN
1 stop6h 35m
Southwest
Deal found 7/16![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 7/17. 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 9/115:03 pm
JAN
- ORD
1 stop6h 56m
Delta
Mon 9/143:40 pm
ORD
- JAN
1 stop4h 55m
Delta
Deal found 7/17![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 7/20. 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.
Mon 10/511:08 am
JAN
- MDW
1 stop5h 07m
Delta
Thu 10/810:58 am
MDW
- JAN
1 stop5h 19m
Delta
Deal found 7/20![Delta logo]()
$335
This Southwest deal was found by Cheapflights users on 7/20. 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.
Sun 8/1612:35 pm
JAN
- MDW
1 stop6h 10m
Southwest
Wed 8/192:05 pm
MDW
- JAN
1 stop5h 40m
Southwest
Deal found 7/20![Southwest logo]()
$365
This Delta deal was found by Cheapflights users on 7/16. 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.
Thu 10/297:51 am
JAN
- ORD
1 stop6h 36m
Delta
Sun 11/15:30 am
ORD
- JAN
1 stop4h 24m
Delta
Deal found 7/16![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 7/18. 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
JAN
- MDW
2 stops6h 50m
Southwest
Mon 9/145:30 am
MDW
- JAN
2 stops6h 30m
Southwest
Deal found 7/18![Southwest logo]()
$366
This Delta deal was found by Cheapflights users on 7/16. 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.
Fri 8/215:01 pm
JAN
- MDW
1 stop5h 35m
Delta
Mon 8/246:05 am
MDW
- JAN
1 stop4h 32m
Delta
Deal found 7/16![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:40 pm
JAN
- MDW
1 stop4h 15m
Southwest
Sun 9/137:20 am
MDW
- JAN
1 stop4h 30m
Southwest
Deal found 7/19![Southwest logo]()
$376
This Delta deal was found by Cheapflights users on 7/17. 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.
Thu 8/275:01 pm
JAN
- MDW
1 stop5h 35m
Delta
Sat 8/296:11 am
MDW
- JAN
1 stop5h 48m
Delta
Deal found 7/17![Delta logo]()
$345
This United Airlines deal was found by Cheapflights users on 7/16. 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.
Fri 8/2812:00 pm
JAN
- ORD
1 stop6h 30m
United Airlines
Mon 8/317:00 am
ORD
- JAN
2 stops13h 05m
United Airlines
Deal found 7/16![United Airlines logo]()
$573
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:04 pm
JAN
- ORD
1 stop5h 55m
Delta
Sun 10/188:05 am
ORD
- JAN
1 stop6h 33m
Delta
Deal found 7/19![Delta logo]()
$356
This United Airlines deal was found by Cheapflights users on 7/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:10 pm
JAN
- ORD
1 stop7h 35m
United Airlines
Sat 8/82:15 pm
ORD
- JAN
1 stop5h 55m
United Airlines
Deal found 7/20![United Airlines logo]()
$579
This United Airlines deal was found by Cheapflights users on 7/21. 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.
Wed 9/22:05 pm
JAN
- ORD
1 stop9h 21m
United Airlines
Mon 9/78:57 am
ORD
- JAN
2 stops13h 01m
United Airlines
Deal found 7/21![United Airlines logo]()
$663
Last-minute flights from Jackson to ChicagoDiscover last-minute flight deals from Jackson to Chicago. Data last updated July 21, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chicago. Data last updated July 21, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/17. 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.
Thu 8/612:40 pm
JAN
- MDW
1 stop4h 15m
Southwest
Wed 8/122:40 pm
MDW
- JAN
1 stop3h 25m
Southwest
Deal found 7/17![Southwest logo]()
$335
This Southwest deal was found by Cheapflights users on 7/20. 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.
Wed 8/121:30 pm
JAN
- MDW
1 stop6h 40m
Southwest
Sat 8/151:45 pm
MDW
- JAN
1 stop5h 20m
Southwest
Deal found 7/20![Southwest logo]()
$303
This American Airlines deal was found by Cheapflights users on 7/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:01 pm
JAN
- ORD
1 stop5h 41m
American Airlines
Sat 8/155:52 pm
ORD
- JAN
1 stop4h 47m
American Airlines
Deal found 7/20![American Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 7/20. 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.
Thu 8/1312:40 pm
JAN
- MDW
1 stop4h 15m
Southwest
Sun 8/167:20 am
MDW
- JAN
1 stop4h 30m
Southwest
Deal found 7/20![Southwest logo]()
$365
This Southwest deal was found by Cheapflights users on 7/20. 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.
Sun 8/1612:35 pm
JAN
- MDW
1 stop6h 10m
Southwest
Wed 8/196:00 am
MDW
- JAN
2 stops6h 50m
Southwest
Deal found 7/20![Southwest logo]()
$370
This Delta deal was found by Cheapflights users on 7/20. 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.
Wed 8/195:01 pm
JAN
- ORD
1 stop6h 56m
Delta
Wed 8/265:30 am
ORD
- JAN
1 stop5h 07m
Delta
Deal found 7/20![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 7/20. 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.
Wed 8/197:05 am
JAN
- MDW
2 stops8h 55m
Southwest
Wed 8/2611:10 am
MDW
- JAN
2 stops8h 35m
Southwest
Deal found 7/20![Southwest logo]()
$313
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:28 pm
JAN
- ORD
1 stop6h 50m
American Airlines
Sat 8/225:00 am
ORD
- JAN
1 stop6h 50m
American Airlines
Deal found 7/19![American Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 7/16. 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.
Thu 8/205:01 pm
JAN
- MDW
1 stop5h 35m
Delta
Sat 8/226:11 am
MDW
- JAN
1 stop5h 48m
Delta
Deal found 7/16![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 7/17. 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.
Thu 8/2012:40 pm
JAN
- MDW
1 stop4h 15m
Southwest
Sun 8/2311:10 am
MDW
- JAN
2 stops9h 05m
Southwest
Deal found 7/17![Southwest logo]()
$381
This American Airlines deal was found by Cheapflights users on 7/16. 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 8/2112:22 pm
JAN
- ORD
1 stop6h 07m
American Airlines
Mon 8/245:49 pm
ORD
- JAN
1 stop4h 50m
American Airlines
Deal found 7/16![American Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 7/17. 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.
Thu 8/275:55 am
JAN
- MDW
1 stop10h 45m
Southwest
Sat 8/297:40 am
MDW
- JAN
2 stops6h 15m
Southwest
Deal found 7/17![Southwest logo]()
$346
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 July 21, 2026.
Search for one-way flight options from Jackson to Chicago. Find affordable one-way fares based on user searches. Data last updated July 21, 2026.
This American Airlines deal was found by Cheapflights users on 7/17. 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 8/1912:22 pm
JAN
- ORD
1 stop8h 08m
American Airlines
Deal found 7/17![American Airlines logo]()
$152
This Delta deal was found by Cheapflights users on 7/20. 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 8/2511:24 am
JAN
- MDW
1 stop4h 51m
Delta
Deal found 7/20![Delta logo]()
$152
This Southwest deal was found by Cheapflights users on 7/20. 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.
Tue 8/257:05 am
JAN
- MDW
2 stops8h 15m
Southwest
Deal found 7/20![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 7/20. 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 9/291:03 pm
JAN
- ORD
1 stop5h 42m
Delta
Deal found 7/20![Delta logo]()
$163
This Delta deal was found by Cheapflights users on 7/20. 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 9/295:35 am
JAN
- MDW
1 stop6h 19m
Delta
Deal found 7/20![Delta logo]()
$163
This Southwest deal was found by Cheapflights users on 7/18. 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 9/1712:40 pm
JAN
- MDW
1 stop7h 30m
Southwest
Deal found 7/18![Southwest logo]()
$168
This Delta deal was found by Cheapflights users on 7/16. 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.
Sun 8/99:15 am
JAN
- ORD
1 stop7h 36m
Delta
Deal found 7/16![Delta logo]()
$204
This Delta deal was found by Cheapflights users on 7/20. 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.
Wed 8/55:01 pm
JAN
- ORD
1 stop6h 56m
Delta
Deal found 7/20![Delta logo]()
$234
This Delta deal was found by Cheapflights users on 7/18. 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.
Sat 8/15:04 pm
JAN
- MDW
1 stop5h 11m
Delta
Deal found 7/18![Delta logo]()
$234
This American Airlines deal was found by Cheapflights users on 7/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:16 am
JAN
- ORD
1 stop7h 44m
American Airlines
Deal found 7/18![American Airlines logo]()
$237
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/25:30 am
JAN
- MDW
2 stops9h 05m
Southwest
Deal found 7/19![Southwest logo]()
$239
This United Airlines deal was found by Cheapflights users on 7/18. 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 7/295:10 pm
JAN
- ORD
1 stop6h 05m
United Airlines
Deal found 7/18![United Airlines logo]()
$267
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 July 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $303 (Delta) |
One-way from | $152 (American Airlines) |
Popular in | June |
Cheapest in | April |
Average price | $541 |
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 2,558,603 searches. Data last updated July 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 - MDW
JANMDW
Jackson-Evers Intl
Wed 8/12
1:30 pm-8:10 pm
1 stop6h 40m
Chicago Midway
Sat 8/15
1:45 pm-7:05 pm
1 stop5h 20m
$303
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Fri 9/11
5:03 pm-10:45 pm
1 stop5h 42m
Chicago Midway
Mon 9/14
6:05 am-10:23 am
1 stop4h 18m
$303
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Fri 9/11
12:40 pm-7:30 pm
2 stops6h 50m
Chicago Midway
Mon 9/14
5:25 am-12:00 pm
1 stop6h 35m
$308
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Fri 9/11
5:03 pm-11:59 pm
1 stop6h 56m
Chicago O'Hare Intl
Mon 9/14
3:40 pm-8:35 pm
1 stop4h 55m
$314
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Mon 10/5
11:08 am-4:15 pm
1 stop5h 07m
Chicago Midway
Thu 10/8
10:58 am-4:17 pm
1 stop5h 19m
$335
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Thu 10/29
7:51 am-2:27 pm
1 stop6h 36m
Chicago O'Hare Intl
Sun 11/1
5:30 am-9:54 am
1 stop4h 24m
$345
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Fri 8/21
5:01 pm-10:36 pm
1 stop5h 35m
Chicago Midway
Mon 8/24
6:05 am-10:37 am
1 stop4h 32m
$345
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Thu 8/27
5:01 pm-10:36 pm
1 stop5h 35m
Chicago Midway
Sat 8/29
6:11 am-11:59 am
1 stop5h 48m
$345
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Thu 10/15
1:04 pm-6:59 pm
1 stop5h 55m
Chicago O'Hare Intl
Sun 10/18
8:05 am-2:38 pm
1 stop6h 33m
$356
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Sun 8/16
12:35 pm-6:45 pm
1 stop6h 10m
Chicago Midway
Wed 8/19
2:05 pm-7:45 pm
1 stop5h 40m
$365
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 July.
| 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, August is the cheapest month in which you can book a flight from Jackson, Mississippi to Chicago (average of $317). 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.
How much does it cost to fly round-trip from Jackson, Mississippi to Chicago?
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 July 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.
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from 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
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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 July 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 2,558,603 searches. Data last updated July 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$236 | Average$428 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$249 | Average$342 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$260 | Average$526 | FlexibilityNo cancel fee | On-time71% |