$147 Cheap Flights from Chicago (MDW) to Jackson (JAN)

View $147 flight on Wed, Apr 29, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Evers Intl. Airport (JAN)

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Chicago to Jackson (MDW-JAN)

Prices were available within the past 7 days and start at $147 for one-way flights and $255 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, May 13 - Wed, May 20
MDW
Chicago
JAN
Jackson
$255 Roundtrip, found 6 days ago
$255
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, May 13 from Chicago to Jackson, returning Wed, May 20, priced at $255 found 6 days ago
Southwest Airlines
Wed, May 13 - Wed, May 20
MDW
Chicago
JAN
Jackson
$275 Roundtrip, found 6 days ago
$275
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, May 13 from Chicago to Jackson, returning Wed, May 20, priced at $275 found 6 days ago
Southwest Airlines
Wed, May 13 - Wed, May 20
MDW
Chicago
JAN
Jackson
$280 Roundtrip, found 6 days ago
$280
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, May 13 from Chicago to Jackson, returning Wed, May 20, priced at $280 found 6 days ago
Southwest Airlines
Wed, Apr 29 - Wed, May 6
MDW
Chicago
JAN
Jackson
$283 Roundtrip, found 3 days ago
$283
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Apr 29 from Chicago to Jackson, returning Wed, May 6, priced at $283 found 3 days ago
Southwest Airlines
Wed, May 20 - Tue, May 26
MDW
Chicago
JAN
Jackson
$303 Roundtrip, found 1 day ago
$303
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, May 20 from Chicago to Jackson, returning Tue, May 26, priced at $303 found 1 day ago
Southwest Airlines
Wed, Apr 15 - Sat, Apr 18
MDW
Chicago
JAN
Jackson
$305 Roundtrip, found 6 hours ago
$305
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Wed, Apr 15 from Chicago to Jackson, returning Sat, Apr 18, priced at $305 found 6 hours ago
Southwest Airlines
Wed, May 20 - Tue, May 26
MDW
Chicago
JAN
Jackson
$308 Roundtrip, found 1 day ago
$308
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, May 20 from Chicago to Jackson, returning Tue, May 26, priced at $308 found 1 day ago
Delta
Wed, Apr 29 - Wed, May 6
MDW
Chicago
JAN
Jackson
$310 Roundtrip, found 3 days ago
$310
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Apr 29 from Chicago to Jackson, returning Wed, May 6, priced at $310 found 3 days ago
Southwest Airlines
Wed, May 6 - Mon, May 11
MDW
Chicago
JAN
Jackson
$310 Roundtrip, found 1 hour ago
$310
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, May 6 from Chicago to Jackson, returning Mon, May 11, priced at $310 found 1 hour ago
Southwest Airlines
Wed, May 20 - Tue, May 26
MDW
Chicago
JAN
Jackson
$313 Roundtrip, found 1 day ago
$313
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, May 20 from Chicago to Jackson, returning Tue, May 26, priced at $313 found 1 day ago

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Alternative airports near Jackson

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Evers Intl. JAN. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $493
JAN
Evers Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $493

Find the cheapest month to fly from Chicago (MDW) to Jackson (JAN)

August is typically the cheapest month to fly

From $178 - $583 per traveler.

Frequently asked questions

How much does a flight from Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.) cost?
You can find cheap one-way flights from $147 and cheap return flights from $255 Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.) with Expedia. One-way flights generally range between $153 and $565, and roundtrip flights usually range from $360 to $1061. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.)?
April is the cheapest month to fly from Chicago, IL (MDW) to Jackson, MS (JAN), with average round-trip fares around $268. This price is about 34% lower than the average throughout the year, as spring travel often sees reduced demand. Other economical months to consider are January and February.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.)?
Enter MDW to JAN and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.)?
Southwest Airlines is one of the cheapest airlines offering connecting flights from Chicago (MDW) to Jackson (JAN), with round-trip tickets starting from around $223. This flight includes a layover in Love Field (DAL). Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.)?
To find a cheap flight from Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.)?
The best time to fly from Chicago Midway (MDW) to Jackson (JAN) is typically in April or February. During these months, you can find return flights at around $268, making them the cheapest options. April offers pleasant spring weather, while February tends to have lower travel demand, allowing for better fares and a more relaxed travel experience.*Prices based on flights available on Expedia in the last year.
What is the earliest flight from Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.)?
The earliest flight from Midway International Airport (MDW) to Evers International Airport (JAN) usually departs at around 5:00 AM. Operated by Southwest Airlines, this early departure allows you to maximize your time in Jackson, Mississippi. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.)?
The most popular departure times for flights from Chicago, IL (MDW) to Jackson, MS (JAN) are from 9am to noon. This accounts for around 37% of total traffic. Many major carriers, including Southwest Airlines and Delta, offer flights during this window. Many travelers prefer this time because it allows for a relaxed start to the day before heading to Jackson.
How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.)?
Flights from MDW to JAN with one stop typically take around 5 hours 30 minutes, covering approximately 667 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.)?
First class seats are offered on the MDW to JAN route with Delta Air Lines.
How do I earn miles on a Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Jackson from Midway Intl. (MDW)?
From Midway Intl. (MDW), you can fly into Evers Intl. (JAN) and McKellar-Sipes Regional (MKL) in Jackson. Some flights may connect through major hubs like Love Field (DAL), Orlando Intl. (MCO), Nashville Intl. (BNA) before reaching Jackson. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.) flight and hotel package?
Securing a Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.)?
If you booked your Chicago, IL (MDW-Midway Intl.) to Jackson, MS (JAN-Evers Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Midway Intl.
Destination airport
Evers Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$255
Distance
667 mi

Book with confidence

Chicago to Jackson Flights

The cheapest times to fly from Chicago to Jackson

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Jackson are during the month of May. You can find some of the cheapest flights from Chicago to Jackson with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Jackson

Sunday is one of the best days to book for cheap flights from Chicago to Jackson: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Jackson

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Jackson in 2026. You can also book with separate airlines for your outbound and return journeys, from $147 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Jackson flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Jackson airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Jackson Flights

*Flight schedules are subject to change.

Explore a world of travel with Expedia

*Available to One Key members.