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$163+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
feb. 20 — feb. 271
vie. 2/20
vie. 2/27
1 adult, Economy
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Cheap flight deals from Jackson to Chicago

Cheapest flights from Jackson to Chicago
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 enero 21, 2026.

This Delta deal was found by Cheapflights users on 1/20. 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.
mié. 2/1112:11 pm
JAN
-
ORD
1 stop7h 10m
Delta
sáb. 2/146:45 am
ORD
-
JAN
1 stop7h 23m
Delta
Deal found 1/20$297
This Delta deal was found by Cheapflights users on 1/20. 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.
mar. 2/175:30 am
JAN
-
MDW
1 stop6h 29m
Delta
mar. 2/246:00 am
MDW
-
JAN
1 stop4h 10m
Delta
Deal found 1/20$297
This Delta deal was found by Cheapflights users on 1/21. 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.
mar. 5/512:55 pm
JAN
-
ORD
1 stop7h 21m
Delta
mar. 5/129:30 am
ORD
-
JAN
1 stop4h 35m
Delta
Deal found 1/21$303
This American Airlines deal was found by Cheapflights users on 1/19. 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.
lun. 2/96:47 am
JAN
-
ORD
1 stop7h 14m
American Airlines
mar. 2/103:23 pm
ORD
-
JAN
1 stop7h 31m
American Airlines
Deal found 1/19$311
This Southwest deal was found by Cheapflights users on 1/19. 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.
lun. 2/94:15 pm
JAN
-
MDW
1 stop5h 10m
Southwest
mar. 2/1010:05 am
MDW
-
JAN
1 stop4h 35m
Southwest
Deal found 1/19$311
This Southwest deal was found by Cheapflights users on 1/19. 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.
lun. 3/211:50 am
JAN
-
MDW
1 stop6h 20m
Southwest
mié. 3/1810:30 am
MDW
-
JAN
2 stops8h 05m
Southwest
Deal found 1/19$319
This Southwest deal was found by Cheapflights users on 1/20. 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.
mié. 2/116:40 am
JAN
-
MDW
2 stops6h 30m
Southwest
sáb. 2/1410:15 am
MDW
-
JAN
2 stops5h 25m
Southwest
Deal found 1/20$322
This Delta deal was found by Cheapflights users on 1/19. 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.
lun. 3/24:58 pm
JAN
-
MDW
1 stop5h 33m
Delta
mié. 3/186:00 am
MDW
-
JAN
1 stop6h 07m
Delta
Deal found 1/19$325
This Southwest deal was found by Cheapflights users on 1/19. 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.
sáb. 2/2112:25 pm
JAN
-
MDW
2 stops7h 15m
Southwest
lun. 2/235:55 am
MDW
-
JAN
1 stop5h 20m
Southwest
Deal found 1/19$330
This Delta deal was found by Cheapflights users on 1/21. 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.
mar. 5/55:11 pm
JAN
-
MDW
1 stop5h 18m
Delta
mar. 5/1210:35 am
MDW
-
JAN
1 stop5h 18m
Delta
Deal found 1/21$335
This Delta deal was found by Cheapflights users on 1/21. 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.
jue. 4/166:59 pm
JAN
-
ORD
1 stop4h 58m
Delta
lun. 4/205:20 am
ORD
-
JAN
1 stop4h 43m
Delta
Deal found 1/21$346
This Delta deal was found by Cheapflights users on 1/20. 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.
sáb. 4/119:55 am
JAN
-
MDW
1 stop5h 30m
Delta
dom. 4/126:00 am
MDW
-
JAN
1 stop6h 07m
Delta
Deal found 1/20$346

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 enero 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$297
(Delta)

One-way from

$163
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$546
Provider with most accurate pricing for Jackson-Evers Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jackson-Evers Intl-Chicago (CHI) flights.
Search Deals
From Jackson-Evers Intl to Chicago (CHI)
Search Deals
One-way flight from Jackson-Evers Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 enero 21, 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

mié. 2/11

7:45 am-1:40 pm

1 stop5h 55m

Chicago O'Hare Intl

sáb. 2/14

5:25 am-11:34 am

1 stop6h 09m

$297

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

mar. 2/17

5:30 am-11:59 am

1 stop6h 29m

Chicago Midway

mar. 2/24

6:00 am-10:10 am

1 stop4h 10m

$297

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

lun. 2/9

6:47 am-2:01 pm

1 stop7h 14m

Chicago O'Hare Intl

mar. 2/10

3:23 pm-10:54 pm

1 stop7h 31m

$311

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

sáb. 2/21

10:13 am-3:21 pm

1 stop5h 08m

Chicago Midway

lun. 2/23

6:40 pm-11:07 pm

1 stop4h 27m

$311

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

lun. 2/9

4:15 pm-9:25 pm

1 stop5h 10m

Chicago Midway

mar. 2/10

1:20 pm-8:00 pm

2 stops6h 40m

$316

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

lun. 3/2

11:50 am-6:10 pm

1 stop6h 20m

Chicago Midway

mié. 3/18

10:30 am-6:35 pm

2 stops8h 05m

$319

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

lun. 3/2

4:58 pm-10:31 pm

1 stop5h 33m

Chicago Midway

mié. 3/18

6:00 am-12:07 pm

1 stop6h 07m

$325

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

sáb. 2/21

12:25 pm-7:40 pm

2 stops7h 15m

Chicago Midway

lun. 2/23

5:55 am-11:15 am

1 stop5h 20m

$330

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

jue. 4/16

6:59 pm-11:57 pm

1 stop4h 58m

Chicago O'Hare Intl

dom. 4/19

7:15 am-12:10 pm

1 stop4h 55m

$346

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

jue. 4/16

6:59 pm-11:57 pm

1 stop4h 58m

Chicago O'Hare Intl

lun. 4/20

5:20 am-10:03 am

1 stop4h 43m

$346

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 37 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 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 Expedia the most. Expedia 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.
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

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 enero 21, 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.
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,089 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,174 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

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

    Located just 6.3 mi from the city center, Jackson-Evers Intl is the airport most travelers will use when flying to Chicago from Jackson. Booking flights from Jackson-Evers Intl (JAN) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 3 different airlines.

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

    For as low as $316, Delta can have you in Chicago from Jackson, Mississippi in 5h 10m. There are 667 mi between Jackson, Mississippi and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Our cheapest airline available from Jackson, Mississippi to Chicago is Delta. Our recent data shows that you can find tickets from as low as $196 on this airline. Additional options worth looking into are Southwest and American Airlines, starting at $234 and $258 round-trip. Users have found that Delta is 53% cheaper than the other options available to this destination.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Jackson to Chicago 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 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Jackson to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 enero 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$196Average$439FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$234Average$392FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$258Average$386FlexibilityNo cancel feeOn-time71%

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