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$119+ 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
Jul 12 — Jul 191
Sat 7/12
Sat 7/19
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 July 7, 2025.

Round-trip from

$213
(Southwest)

One-way from

$119
(Delta)

Popular in

January

Cheapest in

May

Average price

$464
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 July 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 July 7, 2025.

This Southwest deal was found by Cheapflights users on 7/7. 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 9/122:10 pmJAN - MDW
1 stop7h 50mSouthwest
Tue 9/166:25 amMDW - JAN
1 stop6h 15mSouthwest
Deal found 7/7$213
This American Airlines deal was found by Cheapflights users on 7/6. 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 9/97:25 amJAN - ORD
1 stop8h 25mAmerican Airlines
Thu 9/115:00 pmORD - JAN
1 stop5h 31mAmerican Airlines
Deal found 7/6$237
This Delta deal was found by Cheapflights users on 7/6. 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 8/65:50 amJAN - MDW
1 stop6h 08mDelta
Mon 8/116:42 pmMDW - JAN
1 stop4h 38mDelta
Deal found 7/6$237
This Delta deal was found by Cheapflights users on 7/6. 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 8/205:50 amJAN - ORD
1 stop4h 14mDelta
Sun 8/247:05 amORD - JAN
1 stop7h 11mDelta
Deal found 7/6$272
This Southwest deal was found by Cheapflights users on 7/7. 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 9/125:40 amJAN - ORD
2 stops10h 45mSouthwest
Tue 9/167:30 amORD - JAN
2 stops12h 35mSouthwest
Deal found 7/7$279
This United Airlines deal was found by Cheapflights users on 7/6. 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.
Sat 9/612:04 pmJAN - ORD
1 stop5h 06mUnited Airlines
Sat 9/67:53 pmORD - JAN
2 stops15h 24mUnited Airlines
Deal found 7/6$399

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 July 7, 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 8/5

4:10 pm-9:31 pm

1 stop5h 21m

Chicago O'Hare Intl

Tue 8/12

1:21 pm-6:04 pm

1 stop4h 43m

$159

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Tue 8/26

7:05 am-3:20 pm

2 stops8h 15m

Chicago O'Hare Intl

Sat 8/30

7:30 am-7:35 pm

2 stops12h 05m

$184

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 9/12

2:10 pm-10:00 pm

1 stop7h 50m

Chicago Midway

Tue 9/16

6:25 am-12:40 pm

1 stop6h 15m

$213

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 8/6

5:50 am-11:58 am

1 stop6h 08m

Chicago Midway

Mon 8/11

6:42 pm-11:20 pm

1 stop4h 38m

$237

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Wed 8/20

5:50 am-10:04 am

1 stop4h 14m

Chicago O'Hare Intl

Sun 8/24

7:05 am-2:16 pm

1 stop7h 11m

$272

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Tue 8/5

2:07 pm-9:22 am

1 stop19h 15m

Chicago O'Hare Intl

Tue 8/12

9:20 pm-4:01 pm

2 stops18h 41m

$368

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 8/6

3:35 pm-9:42 pm

1 stop6h 07m

$119

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 8/6

7:05 am-3:30 pm

2 stops8h 25m

$149

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Sun 7/27

6:00 am-11:50 am

1 stop5h 50m

$184

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Sun 7/27

6:05 am-4:25 pm

2 stops10h 20m

$230

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/6

Showing 1-10 of 12 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 July 7, 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 July 7, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United 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
4,257 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

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
4,257 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

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
7,963 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

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
8,846 reviews
Southwest
8.0
Very good
4,257 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

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
4,257 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

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 Southwest. Our recent data shows that you can find tickets from as low as $213 on this airline. Additional options worth looking into are American Airlines and Delta, starting at $237 and $237 round-trip. Users have found that Southwest is 51% 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 $119 on Delta. Other airlines that offer cheap prices include Southwest from $149 and American Airlines from $174 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

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 July 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$439FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$306Average$432FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$338Average$392FlexibilityNo cancel feeOn-time63%

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