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$134+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Delta deal was found by Cheapflights users on 10/29. 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 12/1711:17 amJAN - ORD
1 stop4h 03mDelta
Thu 12/255:31 pmORD - JAN
1 stop5h 34mDelta
Deal found 10/29$282
This Delta deal was found by Cheapflights users on 10/29. 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 12/29:16 amJAN - ORD
1 stop7h 29mDelta
Mon 1/127:05 amORD - JAN
1 stop7h 05mDelta
Deal found 10/29$297
This Delta deal was found by Cheapflights users on 10/29. 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 12/912:17 pmJAN - ORD
1 stop6h 26mDelta
Fri 12/1211:15 amORD - JAN
1 stop6h 06mDelta
Deal found 10/29$322
This Delta deal was found by Cheapflights users on 10/29. 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 12/95:48 amJAN - MDW
1 stop4h 06mDelta
Fri 12/1212:50 pmMDW - JAN
1 stop5h 39mDelta
Deal found 10/29$322
This Southwest deal was found by Cheapflights users on 10/29. 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 12/21:10 pmJAN - MDW
1 stop9h 25mSouthwest
Mon 1/1210:05 amMDW - JAN
1 stop4h 35mSouthwest
Deal found 10/29$323
This Southwest deal was found by Cheapflights users on 10/29. 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 12/96:25 amJAN - MDW
2 stops9h 35mSouthwest
Fri 12/125:10 amMDW - JAN
1 stop6h 05mSouthwest
Deal found 10/29$337
This Delta deal was found by Cheapflights users on 10/28. 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 11/255:59 pmJAN - ORD
1 stop6h 03mDelta
Tue 12/21:20 pmORD - JAN
1 stop6h 10mDelta
Deal found 10/28$342
This Delta deal was found by Cheapflights users on 10/28. 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 11/255:59 pmJAN - MDW
1 stop5h 41mDelta
Tue 12/212:50 pmMDW - JAN
1 stop6h 40mDelta
Deal found 10/28$342
This Southwest deal was found by Cheapflights users on 10/28. 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 11/255:20 amJAN - MDW
2 stops8h 45mSouthwest
Tue 12/28:50 amMDW - JAN
1 stop6h 15mSouthwest
Deal found 10/28$347
This Delta deal was found by Cheapflights users on 10/30. 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 12/512:17 pmJAN - ORD
1 stop6h 26mDelta
Sun 12/76:45 amORD - JAN
1 stop4h 45mDelta
Deal found 10/30$357
This Delta deal was found by Cheapflights users on 10/30. 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 12/56:06 pmJAN - MDW
1 stop5h 41mDelta
Sun 12/76:00 amMDW - JAN
1 stop5h 30mDelta
Deal found 10/30$357
This Southwest deal was found by Cheapflights users on 10/30. 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 12/53:40 pmJAN - MDW
1 stop5h 25mSouthwest
Sun 12/79:30 amMDW - JAN
2 stops5h 00mSouthwest
Deal found 10/30$362

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$282
(Delta)

One-way from

$134
(American Airlines)

Popular in

January

Cheapest in

September

Average price

$426
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. 6% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 30, 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 12/17

11:17 am-3:20 pm

1 stop4h 03m

Chicago O'Hare Intl

Thu 12/25

5:31 pm-11:05 pm

1 stop5h 34m

$282

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Tue 3/3

10:40 am-4:39 pm

1 stop5h 59m

Chicago O'Hare Intl

Wed 3/4

7:10 am-11:27 am

1 stop4h 17m

$297

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Tue 12/2

9:16 am-4:45 pm

1 stop7h 29m

Chicago O'Hare Intl

Mon 1/12

7:05 am-2:10 pm

1 stop7h 05m

$297

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Tue 12/9

12:17 pm-6:43 pm

1 stop6h 26m

Chicago O'Hare Intl

Fri 12/12

11:15 am-5:21 pm

1 stop6h 06m

$322

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 1/16

2:57 pm-10:09 pm

1 stop7h 12m

Chicago Midway

Mon 1/19

6:17 pm-11:12 pm

1 stop4h 55m

$322

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 12/2

1:10 pm-10:35 pm

1 stop9h 25m

Chicago Midway

Mon 1/12

10:05 am-2:40 pm

1 stop4h 35m

$323

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 12/9

6:25 am-4:00 pm

2 stops9h 35m

Chicago Midway

Fri 12/12

5:10 am-11:15 am

1 stop6h 05m

$337

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Wed 11/26

5:59 pm-12:02 am

1 stop6h 03m

Chicago O'Hare Intl

Wed 12/3

1:13 pm-7:30 pm

1 stop6h 17m

$342

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 11/25

5:59 pm-11:40 pm

1 stop5h 41m

Chicago Midway

Tue 12/2

12:50 pm-7:30 pm

1 stop6h 40m

$342

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sun 2/22

4:50 pm-10:45 pm

1 stop5h 55m

Chicago Midway

Sat 2/28

5:00 am-11:45 am

1 stop6h 45m

$347

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 39 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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 Jackson, Mississippi-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Jackson, Mississippi-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 December is currently the most expensive (average of $347). 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 October 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Jackson, Mississippi to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 14% on your trip compared to booking a flight in the morning.

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 October 30, 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
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 $282, Delta can have you in Chicago from Jackson, Mississippi in 4h 03m. There are 678 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 54% 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 $134 on American Airlines. Other airlines that offer cheap prices include Delta from $134 and Southwest from $144 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 $196). Flying from Jackson, Mississippi to Chicago in December is currently the most expensive (average of $347). 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
Porter
Benton Harbor

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$196Average$421FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$234Average$406FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$258Average$397FlexibilityNo cancel feeOn-time71%

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