$149+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Mar 5 — Mar 121
1 adult, Economy
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Find cheap flights from Jackson to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Jackson to ChicagoExplore the most affordable flight options available from Jackson to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 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 February 3, 2026.
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 2/2512:19 pm
JAN
- ORD
1 stop4h 32m
Delta
Wed 3/45:25 am
ORD
- JAN
1 stop4h 45m
Delta
Deal found 2/3![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 2/251:25 pm
JAN
- MDW
1 stop4h 40m
Southwest
Wed 3/410:05 am
MDW
- JAN
1 stop4h 35m
Southwest
Deal found 2/3![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 5/55:02 pm
JAN
- ORD
1 stop6h 57m
Delta
Tue 5/126:00 am
ORD
- JAN
1 stop4h 04m
Delta
Deal found 2/3![Delta logo]()
$303
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 5/55:02 pm
JAN
- MDW
1 stop5h 26m
Delta
Tue 5/126:30 am
MDW
- JAN
1 stop5h 43m
Delta
Deal found 2/3![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 5/56:20 pm
JAN
- MDW
1 stop4h 45m
Southwest
Sat 5/95:00 am
MDW
- JAN
1 stop6h 45m
Southwest
Deal found 2/2![Southwest logo]()
$314
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 4/97:06 pm
JAN
- ORD
1 stop4h 48m
Delta
Mon 4/137:14 am
ORD
- JAN
1 stop4h 54m
Delta
Deal found 2/1![Delta logo]()
$325
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 4/115:35 am
JAN
- MDW
1 stop4h 21m
Delta
Mon 4/135:21 pm
MDW
- JAN
1 stop5h 54m
Delta
Deal found 2/3![Delta logo]()
$325
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/46:35 am
JAN
- ORD
1 stop6h 44m
American Airlines
Wed 3/116:10 am
ORD
- JAN
1 stop5h 47m
American Airlines
Deal found 2/2![American Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/41:25 pm
JAN
- MDW
1 stop8h 40m
Southwest
Wed 3/116:25 am
MDW
- JAN
1 stop5h 05m
Southwest
Deal found 2/2![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 5/56:30 am
JAN
- ORD
2 stops11h 55m
Southwest
Sat 5/96:00 am
ORD
- JAN
2 stops13h 15m
Southwest
Deal found 2/2![Southwest logo]()
$345
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 4/166:59 pm
JAN
- ORD
1 stop5h 00m
Delta
Sun 4/195:10 am
ORD
- JAN
1 stop5h 03m
Delta
Deal found 2/1![Delta logo]()
$346
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/285:30 am
JAN
- ORD
1 stop7h 34m
American Airlines
Wed 4/17:12 am
ORD
- JAN
1 stop5h 28m
American Airlines
Deal found 2/2![American Airlines logo]()
$356
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 February 3, 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 February 3, 2026.
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 2/2512:19 pm
JAN
- ORD
1 stop4h 32m
Delta
Wed 3/45:25 am
ORD
- JAN
1 stop4h 45m
Delta
Deal found 2/3![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 2/251:25 pm
JAN
- MDW
1 stop4h 40m
Southwest
Wed 3/410:05 am
MDW
- JAN
1 stop4h 35m
Southwest
Deal found 2/3![Southwest logo]()
$297
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 3/136:42 pm
JAN
- ORD
1 stop5h 34m
American Airlines
Tue 3/1710:28 am
ORD
- JAN
1 stop6h 31m
American Airlines
Deal found 2/3![American Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 5/55:02 pm
JAN
- MDW
1 stop5h 26m
Delta
Tue 5/126:30 am
MDW
- JAN
1 stop5h 43m
Delta
Deal found 2/3![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 5/56:20 pm
JAN
- MDW
1 stop4h 45m
Southwest
Sat 5/95:00 am
MDW
- JAN
1 stop6h 45m
Southwest
Deal found 2/2![Southwest logo]()
$314
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 4/97:06 pm
JAN
- ORD
1 stop4h 48m
Delta
Mon 4/137:14 am
ORD
- JAN
1 stop4h 54m
Delta
Deal found 2/1![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/41:25 pm
JAN
- MDW
1 stop8h 40m
Southwest
Wed 3/116:25 am
MDW
- JAN
1 stop5h 05m
Southwest
Deal found 2/2![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 5/510:59 am
JAN
- ORD
1 stop5h 43m
Delta
Sat 5/97:05 am
ORD
- JAN
1 stop7h 10m
Delta
Deal found 2/2![Delta logo]()
$325
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 4/115:35 am
JAN
- MDW
1 stop4h 21m
Delta
Mon 4/135:21 pm
MDW
- JAN
1 stop5h 54m
Delta
Deal found 2/3![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 4/25:30 am
JAN
- MDW
1 stop5h 05m
Southwest
Mon 4/64:05 pm
MDW
- JAN
1 stop3h 35m
Southwest
Deal found 2/3![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 4/95:45 am
JAN
- MDW
1 stop4h 50m
Southwest
Mon 4/139:00 am
MDW
- JAN
2 stops10h 05m
Southwest
Deal found 2/1![Southwest logo]()
$372
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 4/166:59 pm
JAN
- ORD
1 stop5h 00m
Delta
Sun 4/195:10 am
ORD
- JAN
1 stop5h 03m
Delta
Deal found 2/1![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/285:50 am
JAN
- ORD
2 stops7h 00m
Southwest
Wed 4/12:40 pm
ORD
- JAN
1 stop3h 55m
Southwest
Deal found 2/2![Southwest logo]()
$380
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 4/95:45 am
JAN
- ORD
2 stops9h 45m
Southwest
Mon 4/137:35 pm
ORD
- JAN
2 stops16h 45m
Southwest
Deal found 2/1![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 2/175:35 am
JAN
- ORD
2 stops7h 25m
Southwest
Tue 3/36:05 am
ORD
- JAN
2 stops13h 55m
Southwest
Deal found 2/2![Southwest logo]()
$388
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 4/105:45 am
JAN
- ORD
2 stops9h 45m
Southwest
Sun 4/122:40 pm
ORD
- JAN
1 stop5h 00m
Southwest
Deal found 2/3![Southwest logo]()
$392
Last-minute flights from Jackson to ChicagoDiscover last-minute flight deals from Jackson to Chicago. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Chicago. Data last updated February 3, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 2/1710:57 am
JAN
- ORD
1 stop5h 52m
Delta
Tue 3/35:25 am
ORD
- JAN
1 stop6h 09m
Delta
Deal found 2/2![Delta logo]()
$372
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 2/174:15 pm
JAN
- MDW
1 stop5h 10m
Southwest
Tue 3/39:50 am
MDW
- JAN
1 stop7h 45m
Southwest
Deal found 2/2![Southwest logo]()
$372
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 2/2512:19 pm
JAN
- ORD
1 stop4h 32m
Delta
Wed 3/45:25 am
ORD
- JAN
1 stop4h 45m
Delta
Deal found 2/3![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 2/251:25 pm
JAN
- MDW
1 stop4h 40m
Southwest
Wed 3/410:05 am
MDW
- JAN
1 stop4h 35m
Southwest
Deal found 2/3![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/212:19 pm
JAN
- ORD
1 stop6h 30m
Delta
Mon 3/99:50 am
ORD
- JAN
1 stop6h 30m
Delta
Deal found 2/2![Delta logo]()
$377
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/46:35 am
JAN
- ORD
1 stop6h 44m
American Airlines
Wed 3/116:10 am
ORD
- JAN
1 stop5h 47m
American Airlines
Deal found 2/2![American Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/41:25 pm
JAN
- MDW
1 stop8h 40m
Southwest
Wed 3/116:25 am
MDW
- JAN
1 stop5h 05m
Southwest
Deal found 2/2![Southwest logo]()
$337
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/67:56 pm
JAN
- ORD
1 stop4h 59m
American Airlines
Thu 3/126:10 am
ORD
- JAN
1 stop5h 47m
American Airlines
Deal found 2/2![American Airlines logo]()
$385
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 3/136:42 pm
JAN
- ORD
1 stop5h 34m
American Airlines
Tue 3/1710:28 am
ORD
- JAN
1 stop6h 31m
American Airlines
Deal found 2/3![American Airlines logo]()
$367
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/1912:20 pm
JAN
- MDW
1 stop5h 20m
Southwest
Mon 3/234:05 pm
MDW
- JAN
1 stop3h 35m
Southwest
Deal found 2/2![Southwest logo]()
$367
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/285:30 am
JAN
- ORD
1 stop7h 34m
American Airlines
Wed 4/17:12 am
ORD
- JAN
1 stop5h 28m
American Airlines
Deal found 2/2![American Airlines logo]()
$356
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/285:50 am
JAN
- ORD
2 stops7h 00m
Southwest
Wed 4/12:40 pm
ORD
- JAN
1 stop3h 55m
Southwest
Deal found 2/2![Southwest logo]()
$380
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 February 3, 2026.
Search for one-way flight options from Jackson to Chicago. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This American Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/285:30 am
JAN
- ORD
1 stop7h 34m
American Airlines
Deal found 2/1![American Airlines logo]()
$149
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/2810:13 am
JAN
- MDW
1 stop5h 08m
Delta
Deal found 2/1![Delta logo]()
$149
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 5/1412:58 pm
JAN
- ORD
1 stop5h 37m
Delta
Deal found 2/2![Delta logo]()
$163
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/2812:25 pm
JAN
- ORD
2 stops9h 25m
Southwest
Deal found 2/1![Southwest logo]()
$185
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/286:05 am
JAN
- MDW
2 stops9h 40m
Southwest
Deal found 2/1![Southwest logo]()
$185
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 3/297:06 pm
JAN
- ORD
1 stop4h 48m
Delta
Deal found 2/1![Delta logo]()
$194
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 5/1412:15 pm
JAN
- ORD
2 stops9h 40m
Southwest
Deal found 2/2![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 3/295:35 am
JAN
- MDW
1 stop6h 27m
Delta
Deal found 2/1![Delta logo]()
$230
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 3/295:30 am
JAN
- MDW
2 stops6h 35m
Southwest
Deal found 2/1![Southwest logo]()
$286
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 2/85:32 am
JAN
- ORD
1 stop4h 33m
Delta
Deal found 2/2![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 2/84:58 pm
JAN
- MDW
1 stop5h 24m
Delta
Deal found 2/2![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 2/155:35 am
JAN
- ORD
2 stops7h 25m
Southwest
Deal found 2/3![Southwest logo]()
$294
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 February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $297 (Delta) |
One-way from | $149 (American Airlines) |
Popular in | April |
Cheapest in | September |
Average price | $406 |
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 February 3, 2026.
Use the filters below to find and compare flights from Jackson to Chicago that are best for you.
Fly from
Jackson
Fly to
Chicago
Route
Depart
Return
Price
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Wed 2/25
12:19 pm-4:51 pm
1 stop4h 32m
Chicago O'Hare Intl
Wed 3/4
5:25 am-10:10 am
1 stop4h 45m
$297
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Wed 2/25
1:25 pm-6:05 pm
1 stop4h 40m
Chicago Midway
Wed 3/4
10:05 am-2:40 pm
1 stop4h 35m
$297
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Tue 5/5
5:02 pm-10:28 pm
1 stop5h 26m
Chicago Midway
Tue 5/12
6:30 am-12:13 pm
1 stop5h 43m
$303
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Tue 5/5
6:20 pm-11:05 pm
1 stop4h 45m
Chicago Midway
Sat 5/9
5:00 am-11:45 am
1 stop6h 45m
$314
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Thu 4/9
7:06 pm-11:54 pm
1 stop4h 48m
Chicago O'Hare Intl
Mon 4/13
7:14 am-12:08 pm
1 stop4h 54m
$325
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Tue 5/5
10:59 am-4:42 pm
1 stop5h 43m
Chicago O'Hare Intl
Sat 5/9
7:05 am-2:15 pm
1 stop7h 10m
$325
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Sat 4/11
5:35 am-9:56 am
1 stop4h 21m
Chicago Midway
Mon 4/13
5:21 pm-11:15 pm
1 stop5h 54m
$325
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Wed 3/4
1:25 pm-10:05 pm
1 stop8h 40m
Chicago Midway
Wed 3/11
6:25 am-11:30 am
1 stop5h 05m
$337
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Thu 4/16
6:59 pm-11:59 pm
1 stop5h 00m
Chicago O'Hare Intl
Sun 4/19
5:10 am-10:13 am
1 stop5h 03m
$346
JacksonChicago
JAN - ORD
JANORD
Jackson-Evers Intl
Fri 3/13
6:42 pm-12:16 am
1 stop5h 34m
Chicago O'Hare Intl
Tue 3/17
10:28 am-4:59 pm
1 stop6h 31m
$367
Showing 1-10 of 38 results
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 February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Jackson, Mississippi-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jackson, Mississippi-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Jackson, Mississippi-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Jackson, Mississippi-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Jackson, Mississippi-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Jackson to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Jackson with our price prediction graph.
JAN-CHI
JAN-ORD
JAN-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Jackson to Chicago
JAN-CHI
JAN-ORD
JAN-MDW
What is the cheapest month to book a flight from Jackson, Mississippi to Chicago?
Currently, August is the cheapest month in which you can book a flight from Jackson, Mississippi to Chicago (average of $196). Flying from Jackson, Mississippi to Chicago in May is currently the most expensive (average of $331). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated February 3, 2026.
Get a feel of what it's like to fly with Southwest, Delta, and American 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
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 locationsLansing
Merrillville
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Jackson and Chicago flights
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Other flights from Jackson
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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 February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$196 | Average$421 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$234 | Average$392 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$258 | Average$391 | FlexibilityNo cancel fee | On-time71% |