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$138+ 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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap 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 August 18, 2025.

Round-trip from

$257
(American Airlines)

One-way from

$138
(Delta)

Popular in

January

Cheapest in

May

Average price

$416
From Jackson-Evers Intl to Chicago (CHI)
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One-way flight from Jackson-Evers Intl to Chicago (CHI)
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Highest demand for flights based on searches. 4% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 18, 2025.

This American Airlines deal was found by Cheapflights users on 8/16. 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.
Tue 9/2312:08 pmJAN - ORD
1 stop6h 26mAmerican Airlines
Tue 10/74:17 pmORD - JAN
1 stop6h 14mAmerican Airlines
Deal found 8/16$257
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Tue 12/234:19 pmJAN - ORD
1 stop8h 00mAmerican Airlines
Tue 12/306:38 pmORD - JAN
1 stop5h 06mAmerican Airlines
Deal found 8/16$266
This Southwest deal was found by Cheapflights users on 8/16. 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.
Tue 9/237:05 amJAN - ORD
2 stops8h 15mSouthwest
Tue 10/77:30 amORD - JAN
2 stops13h 10mSouthwest
Deal found 8/16$308
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Thu 11/206:47 amJAN - ORD
1 stop6h 19mAmerican Airlines
Sun 11/235:00 amORD - JAN
1 stop7h 31mAmerican Airlines
Deal found 8/16$311
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Sun 8/313:52 pmJAN - ORD
1 stop5h 21mAmerican Airlines
Thu 9/45:00 pmORD - JAN
1 stop5h 31mAmerican Airlines
Deal found 8/16$312
This Delta deal was found by Cheapflights users on 8/16. 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.
Sun 8/313:01 pmJAN - MDW
1 stop6h 11mDelta
Thu 9/46:00 amMDW - JAN
1 stop6h 24mDelta
Deal found 8/16$312
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/17:43 amJAN - ORD
1 stop6h 36mDelta
Fri 9/59:47 amORD - JAN
1 stop4h 29mDelta
Deal found 8/17$337
This Southwest deal was found by Cheapflights users on 8/17. 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.
Thu 9/252:10 pmJAN - MDW
1 stop7h 25mSouthwest
Sun 9/286:00 amMDW - JAN
1 stop6h 00mSouthwest
Deal found 8/17$341
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Thu 9/256:18 pmJAN - ORD
1 stop5h 34mAmerican Airlines
Sun 9/286:00 amORD - JAN
1 stop5h 33mAmerican Airlines
Deal found 8/16$345
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Fri 9/1912:03 pmJAN - ORD
1 stop6h 31mAmerican Airlines
Sun 9/215:00 amORD - JAN
1 stop7h 04mAmerican Airlines
Deal found 8/16$347
This Southwest deal was found by Cheapflights users on 8/17. 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 11/73:05 pmJAN - MDW
1 stop6h 10mSouthwest
Sun 11/95:10 amMDW - JAN
1 stop6h 05mSouthwest
Deal found 8/17$347
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Thu 9/47:25 amJAN - ORD
1 stop6h 17mAmerican Airlines
Sun 9/75:00 amORD - JAN
1 stop7h 04mAmerican Airlines
Deal found 8/18$354

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 August 18, 2025.
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

Tue 9/23

12:08 pm-6:34 pm

1 stop6h 26m

Chicago O'Hare Intl

Tue 10/7

4:17 pm-10:31 pm

1 stop6h 14m

$257

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Tue 12/23

4:19 pm-12:19 am

1 stop8h 00m

Chicago O'Hare Intl

Tue 12/30

6:38 pm-11:44 pm

1 stop5h 06m

$266

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Tue 9/23

7:05 am-3:20 pm

2 stops8h 15m

Chicago O'Hare Intl

Tue 10/7

7:30 am-8:40 pm

2 stops13h 10m

$308

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Thu 11/20

6:47 am-1:06 pm

1 stop6h 19m

Chicago O'Hare Intl

Sun 11/23

5:00 am-12:31 pm

1 stop7h 31m

$311

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sun 8/31

3:01 pm-9:12 pm

1 stop6h 11m

Chicago Midway

Thu 9/4

6:00 am-12:24 pm

1 stop6h 24m

$312

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Thu 10/16

5:35 am-3:20 pm

2 stops9h 45m

Chicago O'Hare Intl

Mon 10/20

2:50 pm-7:25 pm

1 stop4h 35m

$312

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Sun 8/31

3:52 pm-9:13 pm

1 stop5h 21m

Chicago O'Hare Intl

Thu 9/4

5:00 pm-10:31 pm

1 stop5h 31m

$312

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Mon 9/1

7:43 am-2:19 pm

1 stop6h 36m

Chicago O'Hare Intl

Fri 9/5

9:47 am-2:16 pm

1 stop4h 29m

$337

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 9/25

2:10 pm-9:35 pm

1 stop7h 25m

Chicago Midway

Sun 9/28

6:00 am-12:00 pm

1 stop6h 00m

$341

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Thu 9/25

6:18 pm-11:52 pm

1 stop5h 34m

Chicago O'Hare Intl

Sun 9/28

6:00 am-11:33 am

1 stop5h 33m

$345

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 23 results
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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 $245). Flying from Jackson, Mississippi to Chicago in March is currently the most expensive (average of $321). 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.

What is the cheapest time of day to fly from JAN to CHI?

Find hourly flight availability from Jackson to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 18, 2025.

A simple way to save on the total cost of your ticket is to fly from Jackson, Mississippi to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 40% on your trip compared to booking a flight in the evening.

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 August 18, 2025.
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
4,246 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 $312, American Airlines can have you in Chicago from Jackson, Mississippi in 6h 11m. 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 $286 round-trip. Users have found that Delta is 55% cheaper than the other options available to this destination.

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

    One-way options have recently been found by users for as low as $138 on Delta. Other airlines that offer cheap prices include American Airlines from $169 and Southwest from $209 one-way.

  • 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 $245). Flying from Jackson, Mississippi to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Jackson to Chicago

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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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$196Average$433FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$234Average$392FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$286Average$426FlexibilityNo cancel feeOn-time71%

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