$126+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Jul 10 — Jul 171
Round-trip
1 adult, Economy
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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 June 10, 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 June 10, 2026.
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/175:03 pm
JAN
- MDW
1 stop5h 22m
Delta
Tue 9/226:05 am
MDW
- JAN
1 stop4h 28m
Delta
Deal found 6/10![Delta logo]()
$264
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/176:55 pm
JAN
- ORD
1 stop5h 04m
Delta
Wed 9/238:05 am
ORD
- JAN
1 stop6h 12m
Delta
Deal found 6/10![Delta logo]()
$271
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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
2 stops9h 15m
Southwest
Wed 9/232:05 pm
MDW
- JAN
1 stop5h 40m
Southwest
Deal found 6/10![Southwest logo]()
$283
This American Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:02 pm
JAN
- ORD
1 stop7h 12m
American Airlines
Tue 9/225:00 am
ORD
- JAN
1 stop6h 47m
American Airlines
Deal found 6/8![American Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/185:03 pm
JAN
- MDW
1 stop5h 22m
Delta
Tue 9/226:05 am
MDW
- JAN
1 stop4h 28m
Delta
Deal found 6/8![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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
2 stops9h 15m
Southwest
Tue 9/226:00 am
MDW
- JAN
2 stops6h 50m
Southwest
Deal found 6/10![Southwest logo]()
$288
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/1212:10 pm
JAN
- ORD
1 stop4h 35m
Delta
Thu 9/176:40 am
ORD
- JAN
1 stop5h 37m
Delta
Deal found 6/8![Delta logo]()
$295
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/122:40 pm
JAN
- MDW
1 stop7h 06m
Delta
Thu 9/171:00 pm
MDW
- JAN
1 stop5h 08m
Delta
Deal found 6/8![Delta logo]()
$295
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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
Tue 8/255:49 pm
ORD
- JAN
1 stop4h 51m
American Airlines
Deal found 6/9![American Airlines logo]()
$296
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/126:00 am
JAN
- MDW
2 stops8h 05m
Southwest
Thu 9/175:55 am
MDW
- JAN
1 stop6h 05m
Southwest
Deal found 6/8![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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
JAN
- MDW
2 stops6h 50m
Southwest
Tue 9/227:50 am
MDW
- JAN
1 stop5h 00m
Southwest
Deal found 6/8![Southwest logo]()
$302
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/112:40 pm
JAN
- MDW
1 stop7h 06m
Delta
Mon 9/146:05 am
MDW
- JAN
1 stop6h 12m
Delta
Deal found 6/9![Delta logo]()
$312
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 June 10, 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 June 10, 2026.
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/211:55 am
JAN
- MDW
1 stop7h 35m
Southwest
Tue 8/112:40 pm
MDW
- JAN
1 stop3h 25m
Southwest
Deal found 6/9![Southwest logo]()
$319
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:04 pm
JAN
- ORD
1 stop6h 55m
Delta
Fri 7/101:44 pm
ORD
- JAN
1 stop6h 56m
Delta
Deal found 6/5![Delta logo]()
$373
This United Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:20 am
JAN
- ORD
1 stop9h 10m
United Airlines
Wed 9/308:45 am
ORD
- JAN
1 stop11h 15m
United Airlines
Deal found 6/5![United Airlines logo]()
$485
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 11/217:45 am
JAN
- ORD
1 stop6h 28m
Delta
Sun 11/221:15 pm
ORD
- JAN
1 stop4h 49m
Delta
Deal found 6/8![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3011:25 am
JAN
- MDW
1 stop6h 25m
Southwest
Sat 8/19:15 am
MDW
- JAN
1 stop9h 20m
Southwest
Deal found 6/6![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/175:04 pm
JAN
- ORD
1 stop6h 49m
Delta
Fri 7/245:30 am
ORD
- JAN
1 stop6h 35m
Delta
Deal found 6/8![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:40 pm
JAN
- MDW
1 stop4h 15m
Southwest
Sun 8/2311:10 am
MDW
- JAN
2 stops9h 05m
Southwest
Deal found 6/6![Southwest logo]()
$412
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2111:24 am
JAN
- ORD
1 stop7h 25m
Delta
Mon 8/246:40 am
ORD
- JAN
1 stop5h 32m
Delta
Deal found 6/5![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/286:00 am
JAN
- MDW
2 stops8h 40m
Southwest
Sun 8/25:00 am
MDW
- JAN
2 stops6h 20m
Southwest
Deal found 6/10![Southwest logo]()
$413
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:35 pm
JAN
- ORD
1 stop6h 22m
Delta
Mon 9/149:51 am
ORD
- JAN
1 stop4h 26m
Delta
Deal found 6/6![Delta logo]()
$397
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/112:05 pm
JAN
- ORD
1 stop7h 27m
United Airlines
Mon 9/147:45 pm
ORD
- JAN
2 stops15h 30m
United Airlines
Deal found 6/9![United Airlines logo]()
$564
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:04 pm
JAN
- MDW
1 stop5h 11m
Delta
Tue 7/146:00 am
MDW
- JAN
1 stop6h 05m
Delta
Deal found 6/6![Delta logo]()
$397
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1011:25 am
JAN
- MDW
1 stop10h 35m
Southwest
Sun 7/125:00 am
MDW
- JAN
2 stops6h 20m
Southwest
Deal found 6/9![Southwest logo]()
$458
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/245:04 pm
JAN
- MDW
1 stop5h 11m
Delta
Mon 7/276:00 am
MDW
- JAN
1 stop4h 00m
Delta
Deal found 6/7![Delta logo]()
$423
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/65:10 am
JAN
- MDW
2 stops8h 35m
Southwest
Mon 7/133:00 pm
MDW
- JAN
1 stop7h 00m
Southwest
Deal found 6/8![Southwest logo]()
$473
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/245:10 am
JAN
- MDW
2 stops7h 10m
Southwest
Mon 7/272:45 pm
MDW
- JAN
2 stops7h 15m
Southwest
Deal found 6/7![Southwest logo]()
$478
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/311:25 am
JAN
- MDW
1 stop6h 25m
Southwest
Mon 7/63:00 pm
MDW
- JAN
1 stop7h 00m
Southwest
Deal found 6/10![Southwest logo]()
$483
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/83:06 pm
JAN
- MDW
1 stop7h 09m
Delta
Fri 7/105:10 pm
MDW
- JAN
1 stop5h 59m
Delta
Deal found 6/5![Delta logo]()
$493
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/197:10 pm
JAN
- ORD
1 stop13h 25m
Delta
Tue 7/218:03 am
ORD
- JAN
1 stop4h 02m
Delta
Deal found 6/8![Delta logo]()
$552
Last-minute flights from Jackson to ChicagoDiscover last-minute flight deals from Jackson to Chicago. Data last updated June 10, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chicago. Data last updated June 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/112:20 pm
JAN
- MDW
1 stop4h 45m
Southwest
Tue 7/77:10 am
MDW
- JAN
1 stop4h 35m
Southwest
Deal found 6/5![Southwest logo]()
$383
This American Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:29 pm
JAN
- ORD
1 stop5h 10m
American Airlines
Wed 7/86:04 am
ORD
- JAN
1 stop5h 45m
American Airlines
Deal found 6/7![American Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:04 pm
JAN
- ORD
1 stop6h 55m
Delta
Fri 7/101:44 pm
ORD
- JAN
1 stop6h 56m
Delta
Deal found 6/5![Delta logo]()
$373
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/410:48 am
JAN
- ORD
1 stop6h 29m
Delta
Sat 7/115:30 am
ORD
- JAN
1 stop4h 03m
Delta
Deal found 6/10![Delta logo]()
$358
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/43:55 pm
JAN
- MDW
1 stop4h 45m
Southwest
Sat 7/115:05 am
MDW
- JAN
1 stop6h 40m
Southwest
Deal found 6/8![Southwest logo]()
$358
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/77:15 pm
JAN
- MDW
1 stop4h 40m
Southwest
Tue 7/143:10 pm
MDW
- JAN
1 stop3h 35m
Southwest
Deal found 6/9![Southwest logo]()
$339
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/85:26 pm
JAN
- ORD
1 stop6h 13m
American Airlines
Tue 7/145:45 pm
ORD
- JAN
1 stop6h 03m
American Airlines
Deal found 6/10![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/85:04 pm
JAN
- MDW
1 stop5h 11m
Delta
Tue 7/146:00 am
MDW
- JAN
1 stop4h 00m
Delta
Deal found 6/8![Delta logo]()
$367
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/812:20 pm
JAN
- MDW
2 stops7h 35m
Southwest
Wed 7/155:05 am
MDW
- JAN
2 stops6h 40m
Southwest
Deal found 6/8![Southwest logo]()
$373
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/105:26 pm
JAN
- ORD
1 stop7h 24m
American Airlines
Tue 7/145:00 am
ORD
- JAN
1 stop6h 53m
American Airlines
Deal found 6/9![American Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2812:20 pm
JAN
- MDW
1 stop4h 45m
Southwest
Mon 8/32:45 pm
MDW
- JAN
2 stops7h 15m
Southwest
Deal found 6/5![Southwest logo]()
$368
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3011:25 am
JAN
- MDW
1 stop6h 25m
Southwest
Sat 8/19:15 am
MDW
- JAN
1 stop9h 20m
Southwest
Deal found 6/6![Southwest logo]()
$382
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 June 10, 2026.
Search for one-way flight options from Jackson to Chicago. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/511:24 am
JAN
- ORD
1 stop5h 27m
Delta
Deal found 6/8![Delta logo]()
$126
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/55:32 am
JAN
- MDW
1 stop6h 19m
Delta
Deal found 6/8![Delta logo]()
$126
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/87:15 pm
JAN
- MDW
1 stop4h 40m
Southwest
Deal found 6/8![Southwest logo]()
$170
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/77:15 pm
JAN
- MDW
1 stop4h 40m
Southwest
Deal found 6/6![Southwest logo]()
$184
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:20 pm
JAN
- MDW
2 stops10h 10m
Southwest
Deal found 6/6![Southwest logo]()
$189
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/712:50 pm
JAN
- ORD
1 stop7h 43m
Delta
Deal found 6/6![Delta logo]()
$194
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/23:06 pm
JAN
- MDW
1 stop7h 10m
Delta
Deal found 6/9![Delta logo]()
$194
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/23:06 pm
JAN
- ORD
1 stop5h 27m
Delta
Deal found 6/6![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 6/9![Southwest logo]()
$199
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/65:30 am
JAN
- ORD
1 stop4h 43m
Delta
Deal found 6/8![Delta logo]()
$204
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/510:53 am
JAN
- MDW
1 stop5h 33m
Delta
Deal found 6/6![Delta logo]()
$209
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/237:15 pm
JAN
- MDW
1 stop4h 35m
Southwest
Deal found 6/6![Southwest logo]()
$234
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 June 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $287 (American Airlines) |
One-way from | $126 (Delta) |
Popular in | July |
Cheapest in | September |
Average price | $526 |
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 June 10, 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
Sun 8/2
11:55 am-7:30 pm
1 stop7h 35m
Chicago Midway
Tue 8/11
2:40 pm-6:05 pm
1 stop3h 25m
$319
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Fri 7/3
5:04 pm-11:59 pm
1 stop6h 55m
Chicago O'Hare Intl
Fri 7/10
1:44 pm-8:40 pm
1 stop6h 56m
$373
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Sat 11/21
7:45 am-2:13 pm
1 stop6h 28m
Chicago O'Hare Intl
Sun 11/22
1:15 pm-6:04 pm
1 stop4h 49m
$377
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Thu 7/30
11:25 am-5:50 pm
1 stop6h 25m
Chicago Midway
Sat 8/1
9:15 am-6:35 pm
1 stop9h 20m
$382
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Fri 7/17
5:04 pm-11:53 pm
1 stop6h 49m
Chicago O'Hare Intl
Fri 7/24
5:30 am-12:05 pm
1 stop6h 35m
$387
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Fri 8/21
11:24 am-6:49 pm
1 stop7h 25m
Chicago O'Hare Intl
Mon 8/24
6:40 am-12:12 pm
1 stop5h 32m
$393
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Fri 9/11
5:35 pm-11:57 pm
1 stop6h 22m
Chicago O'Hare Intl
Mon 9/14
9:51 am-2:17 pm
1 stop4h 26m
$397
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Fri 7/10
5:04 pm-10:15 pm
1 stop5h 11m
Chicago Midway
Tue 7/14
6:00 am-12:05 pm
1 stop6h 05m
$397
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Thu 8/20
12:40 pm-4:55 pm
1 stop4h 15m
Chicago Midway
Sun 8/23
11:10 am-8:15 pm
2 stops9h 05m
$412
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Tue 7/28
6:00 am-2:40 pm
2 stops8h 40m
Chicago Midway
Sun 8/2
5:00 am-11:20 am
2 stops6h 20m
$413
Showing 1-10 of 37 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 June.
| 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-MDW
JAN-ORD
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-MDW
JAN-ORD
What is the cheapest month to book a flight from Jackson, Mississippi to Chicago?
Currently, September is the cheapest month in which you can book a flight from Jackson, Mississippi to Chicago (average of $191). Flying from Jackson, Mississippi to Chicago in May is currently the most expensive (average of $372). 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 June 10, 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.
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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
Hammond
Porter
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Other flights to Chicago
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Jackson and Chicago flights
Browse other Jackson and Chicago flight options. Last updated on June 10, 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 June 10, 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 June 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$196 | Average$388 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$234 | Average$417 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$260 | Average$486 | FlexibilityNo cancel fee | On-time71% |