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$144+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$287
(American Airlines)

One-way from

$144
(American Airlines)

Popular in

January

Cheapest in

April

Average price

$406
Provider with most accurate pricing for Jackson-Evers Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Jackson-Evers Intl-Chicago (CHI) flights.
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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. 3% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This American Airlines deal was found by Cheapflights users on 2/19. 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.
Thu 4/109:28 amJAN - ORD
1 stop5h 53mAmerican Airlines
Tue 4/154:45 pmORD - JAN
1 stop7h 08mAmerican Airlines
Deal found 2/19$287
This Southwest deal was found by Cheapflights users on 2/19. 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.
Thu 5/112:20 pmJAN - MDW
1 stop5h 50mSouthwest
Mon 5/55:10 amMDW - JAN
1 stop6h 25mSouthwest
Deal found 2/19$287
This Southwest deal was found by Cheapflights users on 2/19. 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.
Thu 5/15:35 amJAN - ORD
2 stops15h 55mSouthwest
Mon 5/57:00 amORD - JAN
2 stops13h 20mSouthwest
Deal found 2/19$344
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/112:02 pmJAN - ORD
1 stop7h 28mUnited Airlines
Wed 5/149:25 amORD - JAN
1 stop6h 40mUnited Airlines
Deal found 2/20$345
This Delta deal was found by Cheapflights users on 2/19. 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.
Thu 2/2711:07 amJAN - ORD
1 stop6h 18mDelta
Sun 3/27:05 amORD - JAN
1 stop7h 10mDelta
Deal found 2/19$527
This Delta deal was found by Cheapflights users on 2/20. 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.
Thu 2/2711:07 amJAN - MDW
1 stop5h 13mDelta
Sun 3/26:00 amMDW - JAN
1 stop5h 38mDelta
Deal found 2/20$527

Find flights from Jackson to Chicago within your budget

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 February 20, 2025.

Fly from

Jackson

Fly to

Chicago

Route

Depart

Return

Price

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Thu 4/10

9:28 am-3:21 pm

1 stop5h 53m

Chicago O'Hare Intl

Tue 4/15

4:45 pm-11:53 pm

1 stop7h 08m

$287

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 5/1

12:20 pm-6:10 pm

1 stop5h 50m

Chicago Midway

Mon 5/5

5:10 am-11:35 am

1 stop6h 25m

$287

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Thu 5/1

5:35 am-9:30 pm

2 stops15h 55m

Chicago O'Hare Intl

Mon 5/5

7:00 am-8:20 pm

2 stops13h 20m

$344

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Sun 5/11

2:02 pm-9:30 pm

1 stop7h 28m

Chicago O'Hare Intl

Wed 5/14

9:25 am-4:05 pm

1 stop6h 40m

$345

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Thu 2/27

11:07 am-5:25 pm

1 stop6h 18m

Chicago O'Hare Intl

Sun 3/2

7:05 am-2:15 pm

1 stop7h 10m

$527

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 3/6

11:07 am-4:20 pm

1 stop5h 13m

Chicago Midway

Mon 3/10

4:59 pm-11:03 pm

1 stop6h 04m

$559

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Tue 4/8

5:03 am-12:23 pm

1 stop7h 20m

$144

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Mon 4/14

5:11 pm-10:26 pm

1 stop5h 15m

$144

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Mon 4/14

5:35 am-12:10 pm

2 stops6h 35m

$149

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Mon 3/10

7:26 pm-11:56 pm

1 stop4h 30m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 12 results
1
2

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 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 FlightHub the most. FlightHub 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.

Travel insights for flights from Jackson to Chicago

Get recent, data-driven insights about flights from Jackson to Chicago including ideal travel times, pricing trends, and more.

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 February 20, 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 February 20, 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
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 American Airlines. Our recent data shows that you can find tickets from as low as $287 on this airline. Additional options worth looking into are Southwest and United Airlines, starting at $287 and $345 round-trip. Users have found that American Airlines is 35% 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 $144 on American Airlines. Other airlines that offer cheap prices include Delta from $144 and Southwest from $149 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$246Average$494FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$286Average$429FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$338Average$396FlexibilityNo cancel feeOn-time63%
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