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$170+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Jun 8 — Jun 151
Mon 6/8
Mon 6/15
1 adult, Economy
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Cheap 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 May 9, 2026.

This Delta deal was found by Cheapflights users on 5/6. 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.
Tue 6/25:05 pm
JAN
-
ORD
1 stop5h 22m
Delta
Tue 6/95:30 am
ORD
-
JAN
1 stop4h 38m
Delta
Deal found 5/6$339
This Delta deal was found by Cheapflights users on 5/6. 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.
Tue 6/25:05 pm
JAN
-
MDW
1 stop4h 04m
Delta
Tue 6/96:00 am
MDW
-
JAN
1 stop4h 08m
Delta
Deal found 5/6$339
This American Airlines deal was found by Cheapflights users on 5/8. 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.
Mon 6/85:29 pm
JAN
-
ORD
1 stop7h 10m
American Airlines
Tue 6/95:59 am
ORD
-
JAN
1 stop5h 55m
American Airlines
Deal found 5/8$343
This Delta deal was found by Cheapflights users on 5/8. 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 6/85:04 pm
JAN
-
MDW
1 stop5h 13m
Delta
Tue 6/96:00 am
MDW
-
JAN
1 stop4h 08m
Delta
Deal found 5/8$343
This Southwest deal was found by Cheapflights users on 5/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:20 pm
JAN
-
MDW
1 stop4h 45m
Southwest
Wed 6/105:05 am
MDW
-
JAN
2 stops6h 40m
Southwest
Deal found 5/6$344
This Southwest deal was found by Cheapflights users on 5/8. 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 9/126:00 am
JAN
-
MDW
1 stop7h 00m
Southwest
Tue 9/152:05 pm
MDW
-
JAN
1 stop5h 40m
Southwest
Deal found 5/8$347
This Southwest deal was found by Cheapflights users on 5/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/52:30 pm
JAN
-
MDW
1 stop4h 50m
Southwest
Tue 9/81:00 pm
MDW
-
JAN
2 stops5h 05m
Southwest
Deal found 5/6$348
This Delta deal was found by Cheapflights users on 5/5. 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 7/812:50 pm
JAN
-
ORD
1 stop7h 43m
Delta
Fri 7/108:03 am
ORD
-
JAN
1 stop6h 20m
Delta
Deal found 5/5$363
This Delta deal was found by Cheapflights users on 5/6. 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.
Fri 7/103:06 pm
JAN
-
MDW
1 stop7h 09m
Delta
Tue 7/146:00 am
MDW
-
JAN
1 stop6h 05m
Delta
Deal found 5/6$363
This American Airlines deal was found by Cheapflights users on 5/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/612:24 pm
JAN
-
ORD
1 stop7h 35m
American Airlines
Sat 6/1312:33 pm
ORD
-
JAN
1 stop7h 26m
American Airlines
Deal found 5/7$367
This Southwest deal was found by Cheapflights users on 5/7. 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 6/195:10 am
JAN
-
MDW
2 stops8h 35m
Southwest
Wed 6/243:10 pm
MDW
-
JAN
1 stop3h 35m
Southwest
Deal found 5/7$368
This Delta deal was found by Cheapflights users on 5/5. 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 7/223:06 pm
JAN
-
ORD
1 stop5h 27m
Delta
Sun 7/266:35 am
ORD
-
JAN
1 stop5h 30m
Delta
Deal found 5/5$373

Find 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 May 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$319
(American Airlines)

One-way from

$170
(Delta)

Popular in

July

Cheapest in

September

Average price

$438
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 ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 May 9, 2026.
Use the filters below to find and compare flights from Jackson to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Tue 6/2

5:05 pm-10:27 pm

1 stop5h 22m

Chicago O'Hare Intl

Tue 6/9

5:30 am-10:08 am

1 stop4h 38m

$339
Quickest round-trip

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 6/2

5:05 pm-9:09 pm

1 stop4h 04m

Chicago Midway

Tue 6/9

6:00 am-10:08 am

1 stop4h 08m

$339

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sat 9/5

2:30 pm-7:20 pm

1 stop4h 50m

Chicago Midway

Tue 9/8

7:50 am-12:50 pm

1 stop5h 00m

$343

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sat 9/12

6:00 am-1:00 pm

1 stop7h 00m

Chicago Midway

Tue 9/15

11:10 am-7:45 pm

2 stops8h 35m

$352

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Wed 7/22

5:04 pm-11:53 pm

1 stop6h 49m

Chicago O'Hare Intl

Sun 7/26

6:35 am-12:05 pm

1 stop5h 30m

$363

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Sun 6/14

7:00 pm-11:59 pm

1 stop4h 59m

Chicago O'Hare Intl

Wed 6/17

9:48 am-2:26 pm

1 stop4h 38m

$363

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 7/10

3:06 pm-10:15 pm

1 stop7h 09m

Chicago Midway

Tue 7/14

6:00 am-10:00 am

1 stop4h 00m

$363

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 6/19

5:10 am-1:45 pm

2 stops8h 35m

Chicago Midway

Wed 6/24

3:10 pm-6:45 pm

1 stop3h 35m

$368

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Sun 7/19

5:30 am-10:10 am

1 stop4h 40m

Chicago O'Hare Intl

Thu 7/23

9:45 am-2:23 pm

1 stop4h 38m

$387

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Fri 8/14

1:00 pm-6:46 pm

1 stop5h 46m

Chicago O'Hare Intl

Sun 8/16

1:48 pm-6:13 pm

1 stop4h 25m

$387

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/9

Showing 1-10 of 36 resultsSorted by cheapest first
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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 May.
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.

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, September is the cheapest month in which you can book a flight from Jackson, Mississippi to Chicago (average of $191). Flying from Jackson, Mississippi to Chicago in April is currently the most expensive (average of $314). 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.

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 May 9, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andAmerican 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
4,302 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,302 reviews
Southwest
8.0
Very good
4,302 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,457 reviews
Southwest
8.0
Very good
4,302 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,669 reviews
Southwest
8.0
Very good
4,302 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 $343, Delta can have you in Chicago from Jackson, Mississippi in 4h 50m. 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 $258 round-trip. Users have found that Delta is 52% cheaper than the other options available to this destination.

  • 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, September is the cheapest month in which you can book a flight from Jackson, Mississippi to Chicago (average of $191). Flying from Jackson, Mississippi to Chicago in April is currently the most expensive (average of $314). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 May 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$196Average$385FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$234Average$406FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$258Average$457FlexibilityNo cancel feeOn-time71%

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