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$223+ Cheap flights from Chicago (CHI) to Jackson, MS (JAN)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAN
Dec 31 — Jan 71
Wed 12/31
Wed 1/7
1 adult, Economy
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Cheap flight deals from Chicago to Jackson

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Jackson (JAN). 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 December 1, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$223
(Southwest)

Popular in

November

Cheapest in

June

Average price

$426
Provider with most accurate pricing for Chicago (CHI)-Jackson-Evers Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Jackson-Evers Intl flights.
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From Chicago (CHI) to Jackson-Evers Intl
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($73 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Find flight deals from Chicago to Jackson

Cheapest flights from Chicago to Jackson
Explore the most affordable flight options available from Chicago to Jackson. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 1, 2025.

This Southwest deal was found by Cheapflights users on 11/30. Clicking the “Pick Dates” 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 12/3011:45 amMDW - JAN
1 stop5h 45mSouthwest
Tue 1/61:25 pmJAN - MDW
1 stop4h 40mSouthwest
Deal found 11/30$290
This American Airlines deal was found by Cheapflights users on 11/30. Clicking the “Pick Dates” 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 12/309:00 amORD - JAN
1 stop6h 52mAmerican Airlines
Tue 1/65:30 amJAN - ORD
1 stop6h 25mAmerican Airlines
Deal found 11/30$332
This Delta deal was found by Cheapflights users on 12/1. 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.
Tue 12/306:00 amMDW - JAN
1 stop5h 18mDelta
Tue 1/612:11 pmJAN - MDW
1 stop4h 18mDelta
Deal found 12/1$332
This Delta deal was found by Cheapflights users on 11/28. 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.
Fri 12/125:30 amORD - JAN
1 stop6h 00mDelta
Fri 12/1911:17 amJAN - ORD
1 stop5h 31mDelta
Deal found 11/28$417
This Delta deal was found by Cheapflights users on 11/28. 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.
Fri 12/1212:50 pmMDW - JAN
1 stop5h 39mDelta
Fri 12/196:06 pmJAN - MDW
1 stop5h 41mDelta
Deal found 11/28$417
This American Airlines deal was found by Cheapflights users on 11/30. Clicking the “Pick Dates” 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 12/187:11 amORD - JAN
1 stop5h 20mAmerican Airlines
Tue 12/304:22 pmJAN - ORD
1 stop6h 53mAmerican Airlines
Deal found 11/30$439
This Southwest deal was found by Cheapflights users on 11/30. Clicking the “Pick Dates” 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 12/265:00 amMDW - JAN
1 stop6h 05mSouthwest
Mon 12/298:25 pmJAN - MDW
1 stop4h 45mSouthwest
Deal found 11/30$441
This Delta deal was found by Cheapflights users on 11/29. Clicking the “Pick Dates” 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 12/121:20 pmORD - JAN
1 stop4h 01mDelta
Mon 12/159:16 amJAN - ORD
1 stop6h 04mDelta
Deal found 11/29$447
This Delta deal was found by Cheapflights users on 11/29. Clicking the “Pick Dates” 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 12/1212:50 pmMDW - JAN
1 stop4h 31mDelta
Mon 12/1511:17 amJAN - MDW
1 stop5h 17mDelta
Deal found 11/29$447
This Southwest deal was found by Cheapflights users on 11/29. Clicking the “Pick Dates” 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 12/1211:00 amMDW - JAN
1 stop3h 30mSouthwest
Mon 12/151:10 pmJAN - MDW
2 stops7h 55mSouthwest
Deal found 11/29$452
This Southwest deal was found by Cheapflights users on 12/1. 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 12/209:50 amMDW - JAN
2 stops8h 05mSouthwest
Sat 1/35:10 pmJAN - MDW
1 stop6h 10mSouthwest
Deal found 12/1$462
This Southwest deal was found by Cheapflights users on 11/30. Clicking the “Pick Dates” 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 12/306:05 amORD - JAN
2 stops16h 00mSouthwest
Tue 1/66:40 amJAN - ORD
2 stops15h 10mSouthwest
Deal found 11/30$478

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Jackson 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 December 1, 2025.
Use the filters below to find and compare flights from Chicago to Jackson that are best for you.

Fly from

Chicago

Fly to

Jackson

Route

Depart

Return

Price

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 1/31

11:15 am-7:15 pm

1 stop8h 00m

Jackson-Evers Intl

Mon 2/2

6:10 pm-10:55 pm

1 stop4h 45m

$223

ChicagoJackson

ORD - JAN

ORDJAN

Chicago O'Hare Intl

Wed 2/11

9:55 am-4:09 pm

1 stop6h 14m

Jackson-Evers Intl

Sat 2/14

10:13 am-2:10 pm

1 stop3h 57m

$297

ChicagoJackson

ORD - JAN

ORDJAN

Chicago O'Hare Intl

Sat 1/31

10:19 am-4:31 pm

1 stop6h 12m

Jackson-Evers Intl

Mon 2/2

6:47 am-3:17 pm

1 stop8h 30m

$297

ChicagoJackson

ORD - JAN

ORDJAN

Chicago O'Hare Intl

Thu 1/8

2:50 pm-7:36 pm

1 stop4h 46m

Jackson-Evers Intl

Sun 1/11

5:32 am-11:00 am

1 stop5h 28m

$297

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Tue 2/10

6:00 am-11:22 am

1 stop5h 22m

Jackson-Evers Intl

Sat 2/14

5:30 am-10:06 am

1 stop4h 36m

$297

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Fri 1/23

6:14 pm-11:01 pm

1 stop4h 47m

Jackson-Evers Intl

Sun 1/25

4:58 pm-10:22 pm

1 stop5h 24m

$297

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Thu 1/8

6:45 am-2:06 pm

1 stop7h 21m

Jackson-Evers Intl

Sun 1/11

5:32 am-10:27 am

1 stop4h 55m

$297

ChicagoJackson

ORD - JAN

ORDJAN

Chicago O'Hare Intl

Sat 2/28

11:18 am-4:15 pm

1 stop4h 57m

Jackson-Evers Intl

Mon 3/2

9:28 am-1:34 pm

1 stop4h 06m

$309

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 2/28

11:01 am-4:15 pm

1 stop5h 14m

Jackson-Evers Intl

Mon 3/2

10:57 am-5:45 pm

1 stop6h 48m

$309

ChicagoJackson

ORD - JAN

ORDJAN

Chicago O'Hare Intl

Thu 2/26

6:45 am-11:35 am

1 stop4h 50m

Jackson-Evers Intl

Mon 3/2

10:57 am-4:50 pm

1 stop5h 53m

$321

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/29

Showing 1-10 of 35 results
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Compare providers for flights from Chicago to Jackson

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 Chicago to Jackson in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Jackson, Mississippi flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Jackson, Mississippi flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Jackson, Mississippi flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Jackson, Mississippi flights, Cheapflights users trust eDreams the most. eDreams 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 Chicago-Jackson, Mississippi 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 Chicago to Jackson

Have a flexible travel schedule? Discover the best time to fly to Jackson from Chicago with our price prediction graph.
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 Chicago to Jackson

What is the cheapest month to book a flight from Chicago to Jackson, Mississippi?

Currently, April is the cheapest month in which you can book a flight from Chicago to Jackson, Mississippi (average of $164). Flying from Chicago to Jackson, Mississippi in January is currently the most expensive (average of $346). 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 Chicago to Jackson, Mississippi?

What’s the top layover airport for flights from Chicago to Jackson, Mississippi?

Share of 1-stop round-trip flights from Chicago to Jackson, Mississippi chosen by Cheapflights users in the past 12 months, using the same layover each way.

Nashville (BNA) – chosen by Cheapflights users on 63% of 1-stop itineraries from Chicago to Jackson, Mississippi on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Jackson, Mississippi?

Average round-trip fare for 1-stop flights from Chicago to Jackson, Mississippi, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Houston (HOU) is the most affordable 1-stop option, with an average round-trip price of $366.

What’s the fastest layover option from Chicago to Jackson, Mississippi?

Shortest average travel time for 1-stop one-way flights from Chicago to Jackson, Mississippi, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Nashville (BNA) have the shortest average one-way travel time for 1-stop routes: 4h 55m.

Which airport typically offers the quickest layover for flights from Chicago to Jackson, Mississippi?

Average layover duration for 1-stop one-way flights from Chicago to Jackson, Mississippi, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Houston (HOU) offer the fastest connection on this route, with an average layover time of 1h 08m.

Reviews of airlines servicing Jackson

Get insights into the airlines that provide service to Jackson. 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 Jackson. Reviews last updated December 1, 2025.
Read reviews from past customers who have flown Southwest, Delta, and American Airlines from Chicago to Jackson. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,253 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Delta
7.9
Good
8,010 reviews
Southwest
8.0
Very good
4,253 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
American Airlines
7.2
Good
11,041 reviews
Southwest
8.0
Very good
4,253 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Jackson. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Jackson from Chicago?

    If you book a flight to Jackson from Chicago, you will be flying to Jackson-Evers Intl, which is the city’s only airport. Jackson-Evers Intl (JAN) is located 6.3 mi from the center of Jackson. There are 0 flights from Chicago to Jackson-Evers Intl per day from 3 different airlines.

  • How long is the flight from Chicago to Jackson, Mississippi?

    Southwest, Delta, and American Airlines can get you from Chicago to Jackson, Mississippi in just under 6h 12m. Your travel time can differ by up to 1h 48m. Chicago and Jackson, Mississippi are separated by a distance of 678 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Jackson, Mississippi round-trip?

    According to our current data, American Airlines ($236), Delta ($248), and Southwest ($316) offers the cheapest pricing from Chicago to Jackson, Mississippi. Users have found that American Airlines is 46% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Chicago to Jackson, Mississippi one-way?

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $289. American Airlines flights start at $289 while deals on United Airlines start at $289 one-way.

  • Can I find deals for flights from Chicago to Jackson that include hotel bookings?

    Yes. In addition to deals on Chicago to Jackson flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Jackson?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Jackson.

  • Can I find deals for business class flights from Chicago to Jackson?

    Yes. Cheapflights offers flight deals from Chicago to Jackson by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Jackson, Mississippi?

    Currently, April is the cheapest month in which you can book a flight from Chicago to Jackson, Mississippi (average of $164). Flying from Chicago to Jackson, Mississippi in January is currently the most expensive (average of $346). 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.

See more FAQs

Traveling to a place near Jackson?

Book flights to Jackson if you plan to visit one of these locations
Vicksburg
Clinton
Flowood
Pearl

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Top 3 airlines flying from Chicago to Jackson

Discover the top 3 airlines that operate flights from Chicago to Jackson. 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 December 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$236Average$397FlexibilityNo cancel feeOn-time71%
DeltaCheapest$248Average$462FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$316Average$476FlexibilityNo cancel feeOn-time63%

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