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$174+ Cheap flights from Chicago (CHI) to Jackson, MS (JAN)

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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAN
May 19 — May 261
Tue 5/19
Tue 5/26
1 adult, Economy
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Cheap 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 April 19, 2026.

This American Airlines deal was found by Cheapflights users on 4/15. 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 5/236:00 am
ORD
-
JAN
1 stop5h 54m
American Airlines
Tue 5/267:29 pm
JAN
-
ORD
1 stop5h 13m
American Airlines
Deal found 4/15$333
This Southwest deal was found by Cheapflights users on 4/15. 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 5/305:00 am
MDW
-
JAN
1 stop6h 45m
Southwest
Tue 6/21:00 pm
JAN
-
MDW
1 stop3h 45m
Southwest
Deal found 4/15$333
This American Airlines deal was found by Cheapflights users on 4/15. 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 5/1311:15 am
ORD
-
JAN
1 stop6h 54m
American Airlines
Wed 5/206:39 pm
JAN
-
ORD
1 stop5h 15m
American Airlines
Deal found 4/15$349
This American Airlines deal was found by Cheapflights users on 4/16. 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 6/106:00 am
ORD
-
JAN
1 stop5h 54m
American Airlines
Mon 6/157:29 pm
JAN
-
ORD
1 stop5h 06m
American Airlines
Deal found 4/16$353
This Southwest deal was found by Cheapflights users on 4/16. 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 6/103:10 pm
MDW
-
JAN
1 stop3h 35m
Southwest
Mon 6/155:10 am
JAN
-
MDW
1 stop10h 45m
Southwest
Deal found 4/16$358
This American Airlines deal was found by Cheapflights users on 4/18. 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 5/128:39 am
ORD
-
JAN
1 stop8h 17m
American Airlines
Tue 5/267:29 pm
JAN
-
ORD
1 stop5h 13m
American Airlines
Deal found 4/18$362
This Southwest deal was found by Cheapflights users on 4/16. 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 5/76:55 am
MDW
-
JAN
1 stop4h 45m
Southwest
Tue 5/126:20 pm
JAN
-
MDW
1 stop4h 45m
Southwest
Deal found 4/16$363
This Delta deal was found by Cheapflights users on 4/16. 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 6/56:06 pm
ORD
-
JAN
1 stop5h 12m
Delta
Mon 6/87:10 pm
JAN
-
ORD
1 stop4h 49m
Delta
Deal found 4/16$367
This Southwest deal was found by Cheapflights users on 4/17. 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 5/292:40 pm
ORD
-
JAN
1 stop4h 25m
Southwest
Mon 6/15:45 am
JAN
-
ORD
2 stops9h 15m
Southwest
Deal found 4/17$372
This Southwest deal was found by Cheapflights users on 4/15. 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 5/76:55 am
MDW
-
JAN
1 stop4h 45m
Southwest
Sat 5/166:10 pm
JAN
-
MDW
1 stop4h 35m
Southwest
Deal found 4/15$372
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/176:05 am
ORD
-
JAN
1 stop4h 58m
American Airlines
Mon 5/186:39 pm
JAN
-
ORD
1 stop5h 15m
American Airlines
Deal found 4/14$379
This Delta deal was found by Cheapflights users on 4/14. 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 10/161:15 pm
ORD
-
JAN
1 stop6h 51m
Delta
Fri 10/236:59 pm
JAN
-
ORD
1 stop4h 51m
Delta
Deal found 4/14$387

Find 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 April 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$333
(American Airlines)

One-way from

$174
(American Airlines)

Popular in

December

Cheapest in

June

Average price

$534
Provider with most accurate pricing for Chicago (CHI)-Jackson-Evers Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Jackson-Evers Intl flights.
Search Deals
From Chicago (CHI) to Jackson-Evers Intl
Search Deals
One-way flight from Chicago (CHI) to Jackson-Evers Intl
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

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 April 19, 2026.
Use the filters below to find and compare flights from Chicago to Jackson that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoJackson

ORD - JAN

ORDJAN

Chicago O'Hare Intl

Fri 6/5

6:06 pm-11:18 pm

1 stop5h 12m

Jackson-Evers Intl

Mon 6/8

7:10 pm-11:59 pm

1 stop4h 49m

$367
Quickest round-trip

ChicagoJackson

ORD - JAN

ORDJAN

Chicago O'Hare Intl

Sun 5/17

5:30 am-10:04 am

1 stop4h 34m

Jackson-Evers Intl

Mon 5/18

7:23 pm-11:59 pm

1 stop4h 36m

$367

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Thu 5/7

6:55 am-11:40 am

1 stop4h 45m

Jackson-Evers Intl

Tue 5/12

1:00 pm-9:50 pm

2 stops8h 50m

$377

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Fri 8/21

1:00 pm-8:10 pm

1 stop7h 10m

Jackson-Evers Intl

Sat 8/29

6:00 am-1:00 pm

1 stop7h 00m

$387

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 8/22

4:30 pm-11:19 pm

1 stop6h 49m

Jackson-Evers Intl

Sun 8/30

5:35 pm-9:46 pm

1 stop4h 11m

$387

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 8/22

7:20 am-11:50 am

1 stop4h 30m

Jackson-Evers Intl

Sun 8/30

6:15 am-3:50 pm

2 stops9h 35m

$392

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Fri 9/4

5:55 am-12:00 pm

1 stop6h 05m

Jackson-Evers Intl

Mon 9/7

12:40 pm-9:55 pm

2 stops9h 15m

$418

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Wed 7/1

11:25 am-6:45 pm

2 stops7h 20m

Jackson-Evers Intl

Mon 7/6

5:10 am-3:55 pm

1 stop10h 45m

$418

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Fri 7/3

5:41 pm-11:13 pm

1 stop5h 32m

Jackson-Evers Intl

Sun 7/5

9:39 am-4:16 pm

1 stop6h 37m

$421

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Mon 7/6

5:00 am-10:45 am

1 stop5h 45m

Jackson-Evers Intl

Thu 7/9

11:25 am-5:50 pm

1 stop6h 25m

$437

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

Showing 1-10 of 32 resultsSorted by cheapest first
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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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Jackson, Mississippi flight deals on Cheapflights vs. FlightHub >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 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 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, September is the cheapest month in which you can book a flight from Chicago to Jackson, Mississippi (average of $236). Flying from Chicago to Jackson, Mississippi in March is currently the most expensive (average of $366). 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?

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 April 19, 2026.
Read reviews from past customers who have flown Southwest,Delta, andAmerican 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
4,328 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,328 reviews
Southwest
8.0
Very good
4,328 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,422 reviews
Southwest
8.0
Very good
4,328 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,621 reviews
Southwest
8.0
Very good
4,328 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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?

    Delta and Southwest can get you from Chicago to Jackson, Mississippi in just under 4h 45m. Your travel time can differ by up to 27m. Chicago and Jackson, Mississippi are separated by a distance of 667 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 ($270), and Southwest ($316) offers the cheapest pricing from Chicago to Jackson, Mississippi. Users have found that American Airlines is 49% 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 American Airlines, which is currently one of the cheapest options available, starting at $119. Delta flights start at $198 while deals on United Airlines start at $269 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, September is the cheapest month in which you can book a flight from Chicago to Jackson, Mississippi (average of $236). Flying from Chicago to Jackson, Mississippi in March is currently the most expensive (average of $366). 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 April 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$236Average$406FlexibilityNo cancel feeOn-time71%
DeltaCheapest$270Average$478FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$316Average$538FlexibilityNo cancel feeOn-time63%

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