$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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Jul 27 — Aug 31
Round-trip
1 adult, Economy
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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 June 27, 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 27, 2026.
This American Airlines deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/225:00 am
JAN
- ORD
1 stop7h 19m
American Airlines
Wed 7/294:45 pm
ORD
- JAN
1 stop7h 03m
American Airlines
Deal found 6/24![American Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 8/175:55 am
JAN
- MDW
2 stops6h 55m
Southwest
Wed 8/192:05 pm
MDW
- JAN
1 stop5h 40m
Southwest
Deal found 6/25![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/2512:20 pm
JAN
- MDW
2 stops9h 40m
Southwest
Sat 8/88:05 am
MDW
- JAN
1 stop5h 50m
Southwest
Deal found 6/26![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/2212:20 pm
JAN
- MDW
1 stop4h 45m
Southwest
Wed 7/295:05 am
MDW
- JAN
2 stops6h 40m
Southwest
Deal found 6/24![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/226:00 am
JAN
- MDW
2 stops8h 15m
Southwest
Tue 8/2510:10 am
MDW
- JAN
2 stops7h 55m
Southwest
Deal found 6/23![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 8/177:00 pm
JAN
- ORD
1 stop4h 57m
Delta
Wed 8/195:30 am
ORD
- JAN
1 stop5h 07m
Delta
Deal found 6/25![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 6/22![Southwest logo]()
$314
This American Airlines deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/275:28 pm
JAN
- ORD
1 stop6h 50m
American Airlines
Mon 8/316:00 am
ORD
- JAN
1 stop5h 50m
American Airlines
Deal found 6/24![American Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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
Mon 8/316:05 am
MDW
- JAN
1 stop6h 07m
Delta
Deal found 6/24![Delta logo]()
$325
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:49 am
JAN
- ORD
1 stop6h 20m
Delta
Sun 9/65:30 am
ORD
- JAN
1 stop4h 13m
Delta
Deal found 6/23![Delta logo]()
$326
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 stop6h 40m
Southwest
Sun 9/62:10 pm
MDW
- JAN
1 stop5h 40m
Southwest
Deal found 6/23![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/2710:46 am
JAN
- ORD
1 stop6h 26m
Delta
Wed 7/295:30 am
ORD
- JAN
1 stop4h 30m
Delta
Deal found 6/25![Delta logo]()
$345
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 27, 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 27, 2026.
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 8/1712:40 pm
JAN
- MDW
1 stop7h 30m
Southwest
Wed 8/197:50 am
MDW
- JAN
1 stop5h 00m
Southwest
Deal found 6/25![Southwest logo]()
$303
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/1811:24 am
JAN
- ORD
1 stop7h 25m
Delta
Thu 8/208:05 am
ORD
- JAN
1 stop6h 39m
Delta
Deal found 6/22![Delta logo]()
$314
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/132:07 pm
JAN
- ORD
1 stop7h 33m
United Airlines
Fri 7/175:30 am
ORD
- JAN
1 stop5h 54m
United Airlines
Deal found 6/22![United Airlines logo]()
$535
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/2512:20 pm
JAN
- MDW
2 stops9h 40m
Southwest
Sat 8/88:05 am
MDW
- JAN
1 stop5h 50m
Southwest
Deal found 6/26![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/261:30 pm
JAN
- MDW
2 stops8h 20m
Southwest
Sat 8/297:40 am
MDW
- JAN
2 stops6h 15m
Southwest
Deal found 6/22![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 10/2112:10 pm
JAN
- ORD
1 stop6h 22m
Delta
Fri 10/231:15 pm
ORD
- JAN
1 stop6h 51m
Delta
Deal found 6/24![Delta logo]()
$345
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 10/285:35 pm
JAN
- ORD
1 stop6h 15m
Delta
Fri 10/307:10 am
ORD
- JAN
1 stop4h 12m
Delta
Deal found 6/24![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 6/22![Southwest logo]()
$314
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/275:30 am
JAN
- MDW
1 stop4h 35m
Delta
Wed 7/296:00 am
MDW
- JAN
1 stop6h 05m
Delta
Deal found 6/24![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/181:30 pm
JAN
- MDW
1 stop6h 40m
Southwest
Thu 8/205:30 am
MDW
- JAN
2 stops6h 30m
Southwest
Deal found 6/22![Southwest logo]()
$319
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 10/13:02 pm
JAN
- ORD
1 stop5h 53m
Delta
Sun 10/46:40 am
ORD
- JAN
1 stop5h 37m
Delta
Deal found 6/25![Delta logo]()
$356
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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
2 stops6h 50m
Southwest
Mon 8/245:25 am
MDW
- JAN
1 stop6h 35m
Southwest
Deal found 6/25![Southwest logo]()
$330
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 10/286:35 am
JAN
- MDW
2 stops9h 00m
Southwest
Fri 10/306:45 am
MDW
- JAN
1 stop4h 40m
Southwest
Deal found 6/24![Southwest logo]()
$350
This United Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/112:07 pm
JAN
- ORD
1 stop7h 33m
United Airlines
Wed 7/1510:25 am
ORD
- JAN
1 stop5h 50m
United Airlines
Deal found 6/26![United Airlines logo]()
$579
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/75:10 pm
JAN
- ORD
1 stop7h 35m
United Airlines
Sat 7/116:29 am
ORD
- JAN
1 stop7h 03m
United Airlines
Deal found 6/22![United Airlines logo]()
$579
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/207:10 pm
JAN
- ORD
1 stop4h 43m
Delta
Wed 7/228:03 am
ORD
- JAN
1 stop4h 02m
Delta
Deal found 6/23![Delta logo]()
$443
This United Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 12/15:20 pm
JAN
- ORD
1 stop6h 55m
United Airlines
Wed 12/28:10 pm
ORD
- JAN
2 stops15h 03m
United Airlines
Deal found 6/26![United Airlines logo]()
$589
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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
- ORD
1 stop6h 49m
Delta
Fri 7/105:30 am
ORD
- JAN
1 stop4h 30m
Delta
Deal found 6/25![Delta logo]()
$500
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/85:10 pm
JAN
- ORD
1 stop7h 35m
United Airlines
Tue 7/148:11 pm
ORD
- JAN
2 stops15h 13m
United Airlines
Deal found 6/23![United Airlines logo]()
$619
Last-minute flights from Jackson to ChicagoDiscover last-minute flight deals from Jackson to Chicago. Data last updated June 27, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chicago. Data last updated June 27, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/85:00 am
JAN
- ORD
1 stop6h 00m
American Airlines
Wed 7/156:04 am
ORD
- JAN
1 stop5h 45m
American Airlines
Deal found 6/23![American Airlines logo]()
$385
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/157:55 am
JAN
- MDW
1 stop4h 01m
Delta
Tue 7/216:00 am
MDW
- JAN
1 stop4h 00m
Delta
Deal found 6/24![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/157:15 pm
JAN
- MDW
1 stop4h 40m
Southwest
Tue 7/2111:25 am
MDW
- JAN
2 stops7h 20m
Southwest
Deal found 6/23![Southwest logo]()
$360
This American Airlines deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/225:00 am
JAN
- ORD
1 stop7h 19m
American Airlines
Wed 7/294:45 pm
ORD
- JAN
1 stop7h 03m
American Airlines
Deal found 6/24![American Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/2212:20 pm
JAN
- MDW
1 stop4h 45m
Southwest
Wed 7/295:05 am
MDW
- JAN
2 stops6h 40m
Southwest
Deal found 6/24![Southwest logo]()
$308
This American Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/235:26 pm
JAN
- ORD
1 stop7h 24m
American Airlines
Mon 7/275:45 pm
ORD
- JAN
1 stop6h 03m
American Airlines
Deal found 6/23![American Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/2512:20 pm
JAN
- MDW
2 stops9h 40m
Southwest
Sat 8/88:05 am
MDW
- JAN
1 stop5h 50m
Southwest
Deal found 6/26![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/2512:20 pm
JAN
- MDW
2 stops9h 40m
Southwest
Sat 8/15:05 am
MDW
- JAN
1 stop6h 40m
Southwest
Deal found 6/26![Southwest logo]()
$340
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/253:06 pm
JAN
- MDW
1 stop7h 09m
Delta
Sat 8/84:39 pm
MDW
- JAN
1 stop4h 13m
Delta
Deal found 6/26![Delta logo]()
$351
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/2710:46 am
JAN
- ORD
1 stop6h 26m
Delta
Wed 7/295:30 am
ORD
- JAN
1 stop4h 30m
Delta
Deal found 6/25![Delta logo]()
$345
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/275:30 am
JAN
- MDW
1 stop4h 35m
Delta
Wed 7/296:00 am
MDW
- JAN
1 stop6h 05m
Delta
Deal found 6/25![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/2711:25 am
JAN
- MDW
1 stop6h 25m
Southwest
Wed 7/295:05 am
MDW
- JAN
2 stops6h 40m
Southwest
Deal found 6/24![Southwest logo]()
$350
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 27, 2026.
Search for one-way flight options from Jackson to Chicago. Find affordable one-way fares based on user searches. Data last updated June 27, 2026.
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/53:30 pm
JAN
- ORD
1 stop5h 25m
Delta
Deal found 6/23![Delta logo]()
$152
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/255:04 pm
JAN
- MDW
1 stop5h 11m
Delta
Deal found 6/25![Delta logo]()
$152
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/2512:20 pm
JAN
- MDW
2 stops9h 40m
Southwest
Deal found 6/25![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/137:00 pm
JAN
- ORD
1 stop4h 57m
Delta
Deal found 6/23![Delta logo]()
$163
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 10/1510:40 am
JAN
- MDW
1 stop5h 45m
Delta
Deal found 6/23![Delta logo]()
$163
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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
2 stops6h 50m
Southwest
Deal found 6/23![Southwest logo]()
$168
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 6/23![Delta logo]()
$194
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/275:30 am
JAN
- MDW
1 stop4h 35m
Delta
Deal found 6/24![Delta logo]()
$194
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 10/1512:00 pm
JAN
- MDW
2 stops8h 20m
Southwest
Deal found 6/23![Southwest logo]()
$195
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/2711:25 am
JAN
- MDW
1 stop10h 35m
Southwest
Deal found 6/24![Southwest logo]()
$199
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/177:10 pm
JAN
- ORD
1 stop4h 43m
Delta
Deal found 6/25![Delta logo]()
$204
This Southwest deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/2212:20 pm
JAN
- MDW
2 stops7h 35m
Southwest
Deal found 6/24![Southwest logo]()
$209
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 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $303 (American Airlines) |
One-way from | $152 (Delta) |
Popular in | June |
Cheapest in | October |
Average price | $654 |
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 27, 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
Mon 8/17
12:40 pm-8:10 pm
1 stop7h 30m
Chicago Midway
Wed 8/19
7:50 am-12:50 pm
1 stop5h 00m
$303
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Sat 7/25
12:20 pm-10:00 pm
2 stops9h 40m
Chicago Midway
Sat 8/8
8:05 am-1:55 pm
1 stop5h 50m
$305
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Wed 8/26
1:30 pm-9:50 pm
2 stops8h 20m
Chicago Midway
Sat 8/29
7:40 am-1:55 pm
2 stops6h 15m
$313
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Tue 8/18
11:24 am-6:49 pm
1 stop7h 25m
Chicago O'Hare Intl
Thu 8/20
8:05 am-2:44 pm
1 stop6h 39m
$314
Quickest round-trip
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Thu 8/6
12:40 pm-4:55 pm
1 stop4h 15m
Chicago Midway
Wed 8/12
2:40 pm-6:05 pm
1 stop3h 25m
$314
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Tue 8/18
1:30 pm-8:10 pm
1 stop6h 40m
Chicago Midway
Thu 8/20
5:30 am-12:00 pm
2 stops6h 30m
$319
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Thu 8/20
12:40 pm-7:30 pm
2 stops6h 50m
Chicago Midway
Mon 8/24
5:25 am-12:00 pm
1 stop6h 35m
$330
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Wed 10/21
12:10 pm-6:32 pm
1 stop6h 22m
Chicago O'Hare Intl
Fri 10/23
1:15 pm-8:06 pm
1 stop6h 51m
$345
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Wed 10/28
5:35 pm-11:50 pm
1 stop6h 15m
Chicago O'Hare Intl
Fri 10/30
7:10 am-11:22 am
1 stop4h 12m
$345
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Mon 7/27
5:30 am-10:05 am
1 stop4h 35m
Chicago Midway
Wed 7/29
6:00 am-12:05 pm
1 stop6h 05m
$345
Showing 1-10 of 33 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-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, 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 27, 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
Food
7.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Jackson to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
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 27, 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 27, 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 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$196 | Average$329 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$234 | Average$419 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$260 | Average$517 | FlexibilityNo cancel fee | On-time71% |