HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Jackson to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 3, 2025.

Round-trip from

$237
(Delta)

One-way from

$119
(American Airlines)

Popular in

January

Cheapest in

May

Average price

$464
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. 4% potential increase in price ($23 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 July 2025
Search Deals

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 3, 2025.

This Delta deal was found by Cheapflights users on 7/1. 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 8/127:43 amJAN - ORD
1 stop4h 33mDelta
Tue 8/191:30 pmORD - JAN
1 stop7h 07mDelta
Deal found 7/1$237
This Delta deal was found by Cheapflights users on 6/30. 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.
Tue 8/127:43 amJAN - MDW
1 stop4h 05mDelta
Tue 8/196:04 amMDW - JAN
1 stop4h 42mDelta
Deal found 6/30$237
This Southwest deal was found by Cheapflights users on 7/1. 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 9/225:40 amJAN - ORD
2 stops9h 40mSouthwest
Wed 9/247:30 amORD - JAN
2 stops12h 35mSouthwest
Deal found 7/1$253
This Southwest deal was found by Cheapflights users on 7/3. 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 8/207:05 amJAN - MDW
2 stops7h 20mSouthwest
Sun 8/247:10 amMDW - JAN
1 stop7h 15mSouthwest
Deal found 7/3$277
This American Airlines deal was found by Cheapflights users on 7/3. 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 8/19:23 amJAN - ORD
1 stop7h 57mAmerican Airlines
Thu 8/211:21 pmORD - JAN
1 stop6h 04mAmerican Airlines
Deal found 7/3$302
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Tue 8/122:07 pmJAN - ORD
2 stops19h 18mUnited Airlines
Tue 8/196:00 amORD - JAN
1 stop10h 07mUnited Airlines
Deal found 7/1$380

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 3, 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 8/12

7:43 am-12:16 pm

1 stop4h 33m

Chicago O'Hare Intl

Tue 8/19

1:30 pm-8:37 pm

1 stop7h 07m

$237

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 8/12

7:43 am-11:48 am

1 stop4h 05m

Chicago Midway

Tue 8/19

6:04 am-10:46 am

1 stop4h 42m

$237

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Mon 9/22

5:40 am-3:20 pm

2 stops9h 40m

Chicago O'Hare Intl

Wed 9/24

7:30 am-8:05 pm

2 stops12h 35m

$253

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 8/20

7:05 am-2:25 pm

2 stops7h 20m

Chicago Midway

Sun 8/24

7:10 am-2:25 pm

1 stop7h 15m

$277

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Fri 8/1

9:23 am-5:20 pm

1 stop7h 57m

Chicago O'Hare Intl

Thu 8/21

1:21 pm-7:25 pm

1 stop6h 04m

$302

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Tue 8/12

2:07 pm-9:25 am

2 stops19h 18m

Chicago O'Hare Intl

Tue 8/19

6:00 am-4:07 pm

1 stop10h 07m

$380

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Thu 9/4

7:25 am-1:42 pm

1 stop6h 17m

$119

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 8/12

1:15 pm-7:45 pm

1 stop6h 30m

$119

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Tue 8/5

7:05 am-3:20 pm

2 stops8h 15m

$124

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sun 8/17

3:01 pm-9:44 pm

1 stop6h 43m

$158

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

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 July 3, 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 3, 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
4,266 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.6

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
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.6

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
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.6

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
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.6

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
4,266 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.6

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 $237 on this airline. Additional options worth looking into are Southwest and American Airlines, starting at $242 and $302 round-trip. Users have found that Delta is 46% 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 American Airlines. Other airlines that offer cheap prices include Southwest from $119 and Delta from $158 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Jackson to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Memphis to O'Hare Intl flights
Memphis to Midway flights
Jackson to O'Hare Intl flights
Jackson to Midway flights
Baton Rouge to O'Hare Intl flights
Mobile to O'Hare Intl flights
Baton Rouge to Midway flights
Mobile to Midway flights
Memphis to St. Louis flights
Mobile to St. Louis flights
Gulfport to O'Hare Intl flights
Gulfport to St. Louis flights
Gulfport to Midway flights
Baton Rouge to St. Louis flights
Jackson to St. Louis flights
Columbus to O'Hare Intl flights
Columbus to Midway flights
Baton Rouge to Peoria flights
Memphis to Springfield flights
Memphis to Moline flights
Meridian to O'Hare Intl flights
Alexandria to O'Hare Intl flights
Laurel to St. Louis flights
Gulfport to Bloomington flights
Mobile to Moline flights
Laurel to O'Hare Intl flights
Baton Rouge to Moline flights
Memphis to Peoria flights
Columbus to Moline flights
Memphis to Bloomington flights
Baton Rouge to Springfield flights
Mobile to Peoria flights
Gulfport to Moline flights

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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$439FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$306Average$432FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$338Average$392FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2025 Cheapflights