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$129+ 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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$257
(Delta)

One-way from

$129
(American Airlines)

Popular in

January

Cheapest in

May

Average price

$392
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. 5% potential increase in price ($24 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 June 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 June 12, 2025.

This Delta deal was found by Cheapflights users on 6/9. 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 8/131:09 pmJAN - ORD
1 stop6h 00mDelta
Wed 8/209:45 amORD - JAN
1 stop4h 31mDelta
Deal found 6/9$257
This Delta deal was found by Cheapflights users on 6/9. 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 8/197:43 amJAN - MDW
1 stop4h 05mDelta
Tue 8/196:42 pmMDW - JAN
1 stop4h 38mDelta
Deal found 6/9$257
This Southwest deal was found by Cheapflights users on 6/12. 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.
Mon 11/1011:50 amJAN - MDW
2 stops8h 40mSouthwest
Fri 11/149:30 amMDW - JAN
2 stops5h 00mSouthwest
Deal found 6/12$296
This American Airlines deal was found by Cheapflights users on 6/11. 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 8/159:08 amJAN - ORD
1 stop6h 42mAmerican Airlines
Sun 8/176:00 amORD - JAN
1 stop6h 16mAmerican Airlines
Deal found 6/11$315
This Southwest deal was found by Cheapflights users on 6/9. 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 8/1610:15 amJAN - ORD
1 stop6h 10mSouthwest
Mon 8/187:30 amORD - JAN
2 stops12h 40mSouthwest
Deal found 6/9$325
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2512:04 pmJAN - ORD
1 stop12h 11mUnited Airlines
Wed 8/2710:48 amORD - JAN
2 stops11h 06mUnited Airlines
Deal found 6/10$424

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 June 12, 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

Wed 8/13

1:09 pm-7:09 pm

1 stop6h 00m

Chicago O'Hare Intl

Wed 8/20

9:45 am-2:16 pm

1 stop4h 31m

$257

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 8/19

7:43 am-11:48 am

1 stop4h 05m

Chicago Midway

Tue 8/19

6:42 pm-11:20 pm

1 stop4h 38m

$257

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 7/29

12:15 pm-8:35 pm

2 stops8h 20m

Chicago Midway

Tue 8/5

8:35 am-6:10 pm

1 stop9h 35m

$298

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Fri 8/15

9:08 am-3:50 pm

1 stop6h 42m

Chicago O'Hare Intl

Sun 8/17

6:00 am-12:16 pm

1 stop6h 16m

$315

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Sat 8/16

10:15 am-4:25 pm

1 stop6h 10m

Chicago O'Hare Intl

Mon 8/18

7:30 am-8:10 pm

2 stops12h 40m

$325

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Mon 8/25

12:04 pm-12:15 am

1 stop12h 11m

Chicago O'Hare Intl

Wed 8/27

10:48 am-9:54 pm

2 stops11h 06m

$424

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Wed 8/6

11:58 am-6:29 pm

1 stop6h 31m

$129

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 8/6

5:50 am-9:45 am

1 stop3h 55m

$129

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Wed 8/6

7:05 am-3:20 pm

2 stops8h 15m

$134

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 8/6

7:05 am-3:30 pm

2 stops8h 25m

$134

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 11 results
1
2

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 June 12, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Read through reviews of airlines operating flights from Jackson to Chicago, such as Southwest, Delta and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • 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 $257 on this airline. Additional options worth looking into are Southwest and American Airlines, starting at $298 and $315 round-trip. Users have found that Delta is 41% 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 $129 on American Airlines. Other airlines that offer cheap prices include Delta from $129 and Southwest from $134 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 Jackson?

Book flights to Jackson if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$246Average$439FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$306Average$434FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$338Average$396FlexibilityNo cancel feeOn-time63%

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