$189+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
May 28 — Jun 41
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Jackson to Chicago
Cheapest
Best
Last-minute
One-way
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 April 28, 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 April 28, 2026.
This Delta deal was found by Cheapflights users on 4/23. 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 8/206:59 pm
JAN
- ORD
1 stop4h 58m
Delta
Sat 8/225:55 pm
ORD
- JAN
1 stop5h 24m
Delta
Deal found 4/23![Delta logo]()
$303
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/265:05 pm
JAN
- ORD
1 stop5h 22m
Delta
Tue 6/27:07 am
ORD
- JAN
1 stop5h 05m
Delta
Deal found 4/28![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/265:35 am
JAN
- MDW
1 stop4h 25m
Delta
Tue 6/26:23 am
MDW
- JAN
1 stop5h 49m
Delta
Deal found 4/28![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 4/24. 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.
Sat 5/235:00 pm
JAN
- ORD
1 stop4h 46m
Delta
Tue 5/267:07 am
ORD
- JAN
1 stop7h 08m
Delta
Deal found 4/24![Delta logo]()
$333
This Delta deal was found by Cheapflights users on 4/24. 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.
Sat 5/235:00 pm
JAN
- MDW
1 stop4h 09m
Delta
Tue 5/266:23 am
MDW
- JAN
1 stop5h 49m
Delta
Deal found 4/24![Delta logo]()
$333
This Delta deal was found by Cheapflights users on 4/24. 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.
Sat 5/235:00 pm
JAN
- ORD
1 stop7h 07m
Delta
Mon 5/255:30 am
ORD
- JAN
1 stop6h 42m
Delta
Deal found 4/24![Delta logo]()
$347
This American Airlines deal was found by Cheapflights users on 4/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:29 pm
JAN
- ORD
1 stop5h 10m
American Airlines
Tue 6/95:59 am
ORD
- JAN
1 stop5h 55m
American Airlines
Deal found 4/26![American Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 4/26. 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.
Fri 6/511:25 am
JAN
- MDW
1 stop6h 25m
Southwest
Tue 6/91:10 pm
MDW
- JAN
1 stop7h 30m
Southwest
Deal found 4/26![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/265:10 am
JAN
- MDW
2 stops8h 35m
Southwest
Tue 6/307:10 am
MDW
- JAN
1 stop4h 35m
Southwest
Deal found 4/28![Southwest logo]()
$358
This Delta deal was found by Cheapflights users on 4/26. 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.
Wed 5/202:55 pm
JAN
- ORD
1 stop6h 58m
Delta
Sat 5/239:10 am
ORD
- JAN
1 stop5h 05m
Delta
Deal found 4/26![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/107:15 pm
JAN
- MDW
1 stop4h 35m
Southwest
Sat 6/138:00 am
MDW
- JAN
2 stops10h 35m
Southwest
Deal found 4/28![Southwest logo]()
$364
This American Airlines deal was found by Cheapflights users on 4/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/192:20 pm
JAN
- ORD
1 stop8h 00m
American Airlines
Sun 5/247:58 am
ORD
- JAN
1 stop7h 55m
American Airlines
Deal found 4/26![American Airlines logo]()
$367
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 April 28, 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 April 28, 2026.
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/265:05 pm
JAN
- ORD
1 stop5h 22m
Delta
Tue 6/27:07 am
ORD
- JAN
1 stop5h 05m
Delta
Deal found 4/28![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 4/26. 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.
Fri 6/511:25 am
JAN
- MDW
1 stop6h 25m
Southwest
Tue 6/91:10 pm
MDW
- JAN
1 stop7h 30m
Southwest
Deal found 4/26![Southwest logo]()
$353
This United Airlines deal was found by Cheapflights users on 4/26. 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.
Fri 6/55:10 pm
JAN
- ORD
2 stops16h 31m
United Airlines
Tue 6/96:30 am
ORD
- JAN
1 stop7h 02m
United Airlines
Deal found 4/26![United Airlines logo]()
$615
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/265:35 am
JAN
- MDW
1 stop4h 25m
Delta
Tue 6/26:23 am
MDW
- JAN
1 stop5h 49m
Delta
Deal found 4/28![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/265:10 am
JAN
- MDW
2 stops8h 35m
Southwest
Tue 6/307:10 am
MDW
- JAN
1 stop4h 35m
Southwest
Deal found 4/28![Southwest logo]()
$358
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/36:20 pm
JAN
- MDW
1 stop4h 45m
Southwest
Mon 6/811:20 am
MDW
- JAN
1 stop8h 25m
Southwest
Deal found 4/28![Southwest logo]()
$372
This Delta deal was found by Cheapflights users on 4/26. 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.
Thu 8/2010:40 am
JAN
- ORD
1 stop6h 05m
Delta
Sun 8/235:30 am
ORD
- JAN
1 stop5h 48m
Delta
Deal found 4/26![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 4/25. 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 6/1512:57 pm
JAN
- ORD
1 stop5h 45m
Delta
Fri 6/198:08 am
ORD
- JAN
1 stop6h 18m
Delta
Deal found 4/25![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 10/136:35 am
JAN
- MDW
1 stop4h 30m
Southwest
Tue 10/1312:55 pm
MDW
- JAN
1 stop7h 05m
Southwest
Deal found 4/28![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 10/136:59 pm
JAN
- ORD
1 stop4h 51m
Delta
Wed 10/148:15 am
ORD
- JAN
1 stop5h 52m
Delta
Deal found 4/28![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 10/131:05 pm
JAN
- MDW
1 stop4h 05m
Southwest
Wed 10/1412:40 pm
MDW
- JAN
2 stops7h 20m
Southwest
Deal found 4/28![Southwest logo]()
$392
This Southwest deal was found by Cheapflights users on 4/24. 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 7/227:15 pm
JAN
- MDW
1 stop4h 35m
Southwest
Sat 7/259:15 am
MDW
- JAN
2 stops11h 20m
Southwest
Deal found 4/24![Southwest logo]()
$398
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/67:00 pm
JAN
- ORD
1 stop4h 59m
Delta
Mon 7/135:30 am
ORD
- JAN
1 stop6h 35m
Delta
Deal found 4/27![Delta logo]()
$433
This Southwest deal was found by Cheapflights users on 4/26. 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.
Fri 7/1011:25 am
JAN
- MDW
2 stops10h 35m
Southwest
Tue 7/147:10 am
MDW
- JAN
1 stop4h 35m
Southwest
Deal found 4/26![Southwest logo]()
$398
This Southwest deal was found by Cheapflights users on 4/25. 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 6/1111:25 am
JAN
- MDW
2 stops10h 35m
Southwest
Sat 6/137:05 am
MDW
- JAN
1 stop4h 40m
Southwest
Deal found 4/25![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 4/25. 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 6/155:10 am
JAN
- MDW
2 stops8h 35m
Southwest
Fri 6/1911:35 am
MDW
- JAN
1 stop10h 20m
Southwest
Deal found 4/25![Southwest logo]()
$418
This Delta deal was found by Cheapflights users on 4/26. 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.
Fri 5/81:30 pm
JAN
- ORD
1 stop6h 56m
Delta
Sun 5/109:49 am
ORD
- JAN
1 stop4h 26m
Delta
Deal found 4/26![Delta logo]()
$562
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/121:00 pm
JAN
- ORD
2 stops8h 55m
Southwest
Wed 5/1311:55 am
ORD
- JAN
2 stops8h 25m
Southwest
Deal found 4/28![Southwest logo]()
$477
This Southwest deal was found by Cheapflights users on 4/24. 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.
Sat 5/912:20 pm
JAN
- ORD
2 stops9h 35m
Southwest
Mon 5/112:40 pm
ORD
- JAN
1 stop4h 25m
Southwest
Deal found 4/24![Southwest logo]()
$482
This Southwest deal was found by Cheapflights users on 4/24. 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.
Thu 5/145:45 am
JAN
- ORD
2 stops9h 45m
Southwest
Sun 5/177:35 pm
ORD
- JAN
2 stops16h 05m
Southwest
Deal found 4/24![Southwest logo]()
$558
This Southwest deal was found by Cheapflights users on 4/25. 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.
Fri 5/85:45 am
JAN
- ORD
2 stops9h 45m
Southwest
Sun 5/106:00 am
ORD
- JAN
2 stops13h 40m
Southwest
Deal found 4/25![Southwest logo]()
$578
Last-minute flights from Jackson to ChicagoDiscover last-minute flight deals from Jackson to Chicago. Data last updated April 28, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chicago. Data last updated April 28, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 4/24. 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.
Fri 5/85:00 pm
JAN
- ORD
1 stop6h 59m
Delta
Sun 5/108:10 am
ORD
- JAN
1 stop4h 33m
Delta
Deal found 4/24![Delta logo]()
$467
This Southwest deal was found by Cheapflights users on 4/24. 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.
Fri 5/85:45 am
JAN
- ORD
2 stops9h 45m
Southwest
Sun 5/102:40 pm
ORD
- JAN
1 stop5h 00m
Southwest
Deal found 4/24![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 4/24. 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.
Fri 5/157:45 pm
JAN
- MDW
2 stops9h 15m
Southwest
Sat 5/1610:00 am
MDW
- JAN
2 stops9h 15m
Southwest
Deal found 4/24![Southwest logo]()
$397
This Southwest deal was found by Cheapflights users on 4/26. 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.
Tue 5/196:20 pm
JAN
- MDW
1 stop4h 45m
Southwest
Sun 5/247:30 am
MDW
- JAN
1 stop4h 55m
Southwest
Deal found 4/26![Southwest logo]()
$393
This Delta deal was found by Cheapflights users on 4/24. 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.
Sat 5/235:00 pm
JAN
- MDW
1 stop4h 09m
Delta
Tue 5/266:23 am
MDW
- JAN
1 stop5h 49m
Delta
Deal found 4/24![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 4/24. 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.
Sat 5/236:10 pm
JAN
- MDW
1 stop4h 35m
Southwest
Tue 5/2611:35 am
MDW
- JAN
2 stops8h 45m
Southwest
Deal found 4/24![Southwest logo]()
$412
This Delta deal was found by Cheapflights users on 4/24. 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.
Sat 5/235:00 pm
JAN
- MDW
1 stop4h 09m
Delta
Mon 5/256:23 am
MDW
- JAN
1 stop5h 49m
Delta
Deal found 4/24![Delta logo]()
$413
This Southwest deal was found by Cheapflights users on 4/26. 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.
Sun 5/241:20 pm
JAN
- MDW
2 stops9h 25m
Southwest
Sun 5/315:00 am
MDW
- JAN
2 stops6h 55m
Southwest
Deal found 4/26![Southwest logo]()
$417
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/265:35 am
JAN
- MDW
1 stop4h 25m
Delta
Tue 6/26:23 am
MDW
- JAN
1 stop5h 49m
Delta
Deal found 4/28![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/266:20 pm
JAN
- MDW
1 stop4h 45m
Southwest
Tue 6/28:15 am
MDW
- JAN
2 stops9h 15m
Southwest
Deal found 4/28![Southwest logo]()
$378
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/2812:15 pm
JAN
- MDW
1 stop4h 45m
Southwest
Sun 5/315:00 am
MDW
- JAN
2 stops6h 55m
Southwest
Deal found 4/28![Southwest logo]()
$392
This Southwest deal was found by Cheapflights users on 4/24. 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.
Fri 5/295:45 am
JAN
- MDW
1 stop9h 40m
Southwest
Sun 5/3111:05 am
MDW
- JAN
1 stop8h 35m
Southwest
Deal found 4/24![Southwest logo]()
$398
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 April 28, 2026.
Search for one-way flight options from Jackson to Chicago. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
This KAYAK deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:35 am
JAN
- ORD
1 stop4h 41m
Delta
Deal found 4/27![Delta logo]()
$189
This American Airlines deal was found by Cheapflights users on 4/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:27 am
JAN
- ORD
1 stop6h 28m
American Airlines
Deal found 4/25![American Airlines logo]()
$194
This Delta deal was found by Cheapflights users on 4/24. 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.
Fri 5/157:23 pm
JAN
- ORD
1 stop4h 36m
Delta
Deal found 4/24![Delta logo]()
$204
This Southwest deal was found by Cheapflights users on 4/24. 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.
Sun 5/246:00 pm
JAN
- ORD
2 stops15h 45m
Southwest
Deal found 4/24![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 4/25. 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.
Sun 5/241:20 pm
JAN
- MDW
1 stop6h 30m
Southwest
Deal found 4/25![Southwest logo]()
$214
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/156:05 pm
JAN
- ORD
1 stop5h 43m
American Airlines
Deal found 4/28![American Airlines logo]()
$234
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/155:00 pm
JAN
- MDW
1 stop4h 09m
Delta
Deal found 4/27![Delta logo]()
$234
This KAYAK deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:15 am
JAN
- ORD
2 stops12h 12m
American Airlines
Deal found 4/27![American Airlines logo]()
$242
This Southwest deal was found by Cheapflights users on 4/24. 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 5/1112:15 pm
JAN
- MDW
2 stops8h 20m
Southwest
Deal found 4/24![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 4/24. 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.
Sun 5/36:59 pm
JAN
- ORD
1 stop5h 00m
Delta
Deal found 4/24![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 4/25. 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.
Sun 5/35:36 am
JAN
- MDW
1 stop4h 20m
Delta
Deal found 4/25![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 4/24. 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.
Sun 5/35:55 am
JAN
- ORD
2 stops9h 35m
Southwest
Deal found 4/24![Southwest logo]()
$334
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 April 28, 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 | July |
Cheapest in | September |
Average price | $346 |
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 April 28, 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 - ORD
JANORD
Jackson-Evers Intl
Tue 5/26
5:05 pm-10:27 pm
1 stop5h 22m
Chicago O'Hare Intl
Tue 6/2
7:07 am-12:12 pm
1 stop5h 05m
$319
Quickest round-trip
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Tue 5/26
5:35 am-10:00 am
1 stop4h 25m
Chicago Midway
Tue 6/2
6:23 am-12:12 pm
1 stop5h 49m
$319
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Fri 6/5
11:25 am-5:50 pm
1 stop6h 25m
Chicago Midway
Tue 6/9
1:10 pm-8:40 pm
1 stop7h 30m
$353
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Fri 6/26
5:10 am-1:45 pm
2 stops8h 35m
Chicago Midway
Tue 6/30
7:10 am-11:45 am
1 stop4h 35m
$358
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Wed 6/3
6:20 pm-11:05 pm
1 stop4h 45m
Chicago Midway
Mon 6/8
11:20 am-7:45 pm
1 stop8h 25m
$372
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Thu 8/20
10:40 am-4:45 pm
1 stop6h 05m
Chicago O'Hare Intl
Sun 8/23
5:30 am-11:18 am
1 stop5h 48m
$387
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Mon 6/15
12:57 pm-6:42 pm
1 stop5h 45m
Chicago O'Hare Intl
Fri 6/19
8:08 am-2:26 pm
1 stop6h 18m
$387
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Tue 10/13
6:35 am-11:05 am
1 stop4h 30m
Chicago Midway
Tue 10/13
12:55 pm-8:00 pm
1 stop7h 05m
$387
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Tue 10/13
6:59 pm-11:50 pm
1 stop4h 51m
Chicago O'Hare Intl
Wed 10/14
8:15 am-2:07 pm
1 stop5h 52m
$387
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Tue 10/13
1:05 pm-5:10 pm
1 stop4h 05m
Chicago Midway
Wed 10/14
12:40 pm-8:00 pm
2 stops7h 20m
$392
Showing 1-10 of 35 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 April.
| 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 April is currently the most expensive (average of $314). 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 April 28, 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.
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Jackson
Popular flights
Alternative routes for Jackson to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 28, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Jackson to Chicago by cabin class
Find flights from Jackson to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Jackson and Chicago flights
Browse other Jackson and Chicago flight options. Last updated on April 28, 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 April 28, 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 April 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$196 | Average$385 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$234 | Average$416 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$258 | Average$457 | FlexibilityNo cancel fee | On-time71% |