$119 Cheap Flights from Chicago (MDW) to Jackson (JAN)

View $119 flight on Fri, Oct 31, 2025Opens in a new window

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

Cheap Flights from Chicago to Jackson (MDW-JAN)

Prices were available within the past 7 days and start at $119 for one-way flights and $257 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Nov 18 - Mon, Nov 24
MDW
Chicago
JAN
Jackson
$257 Roundtrip, found 5 days ago
$257
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Nov 18 from Chicago to Jackson, returning Mon, Nov 24, priced at $257 found 5 days ago
Delta
Mon, Nov 24 - Thu, Nov 27
MDW
Chicago
JAN
Jackson
$267 Roundtrip, found 2 days ago
$267
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Nov 24 from Chicago to Jackson, returning Thu, Nov 27, priced at $267 found 2 days ago
Southwest Airlines
Sat, Jan 17 - Tue, Jan 20
MDW
Chicago
JAN
Jackson
$267 Roundtrip, found 19 hours ago
$267
Roundtrip
found 19 hours ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Chicago to Jackson, returning Tue, Jan 20, priced at $267 found 19 hours ago
Southwest Airlines
Sat, Jan 17 - Tue, Jan 20
MDW
Chicago
JAN
Jackson
$272 Roundtrip, found 19 hours ago
$272
Roundtrip
found 19 hours ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Chicago to Jackson, returning Tue, Jan 20, priced at $272 found 19 hours ago
Delta
Wed, Nov 5 - Tue, Nov 11
MDW
Chicago
JAN
Jackson
$277 Roundtrip, found 5 days ago
$277
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Nov 5 from Chicago to Jackson, returning Tue, Nov 11, priced at $277 found 5 days ago
Southwest Airlines
Fri, Oct 31 - Tue, Nov 4
MDW
Chicago
JAN
Jackson
$277 Roundtrip, found 1 day ago
$277
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Chicago to Jackson, returning Tue, Nov 4, priced at $277 found 1 day ago
Southwest Airlines
Mon, Nov 24 - Thu, Nov 27
MDW
Chicago
JAN
Jackson
$282 Roundtrip, found 2 days ago
$282
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Nov 24 from Chicago to Jackson, returning Thu, Nov 27, priced at $282 found 2 days ago
Southwest Airlines
Fri, Oct 31 - Tue, Nov 4
MDW
Chicago
JAN
Jackson
$282 Roundtrip, found 1 day ago
$282
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Chicago to Jackson, returning Tue, Nov 4, priced at $282 found 1 day ago
Southwest Airlines
Wed, Dec 3 - Mon, Dec 8
MDW
Chicago
JAN
Jackson
$287 Roundtrip, found 2 hours ago
$287
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Dec 3 from Chicago to Jackson, returning Mon, Dec 8, priced at $287 found 2 hours ago
Southwest Airlines
Sat, Nov 22 - Mon, Nov 24
MDW
Chicago
JAN
Jackson
$287 Roundtrip, found 1 day ago
$287
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Nov 22 from Chicago to Jackson, returning Mon, Nov 24, priced at $287 found 1 day ago

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.

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 $332
JAN
Evers Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $332

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Evers Intl. Airport (JAN) cost?
Grab a cheap one-way flight from $119 or cheap return flight from $257 from Midway Intl. Airport (MDW) to Evers Intl. Airport (JAN) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Evers Intl. Airport (JAN)?
Planning your trip for November may help you find better deals, as it's the cheapest month for flights between MDW and JAN. You'll typically find the lowest fares during off-peak months.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Evers Intl. Airport (JAN)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest MDW to JAN flight.
How many flights per day from Midway Intl. Airport (MDW) to Evers Intl. Airport (JAN)?
Direct flights from Midway Intl. Airport (MDW) to Evers Intl. Airport (JAN) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filters. Enter your dates and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to JAN?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Evers Intl. Airport (JAN)?
Choose a flight from Midway Intl. Airport (MDW) to Evers Intl. Airport (JAN) that leaves before 3 PM to reduce the risk of cancellations. Departures after this hour have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Evers Intl. Airport (JAN) last-minute?
Booking your plane ticket from MDW to JAN shortly before your trip is typically more expensive. But if there's some wiggle room with your travel times and dates, you could bag a cheap last-minute fare.
Is it cheaper to book a MDW to JAN flight and hotel package?
You can save money by securing a MDW to JAN flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one place. After selecting your ideal flights and accommodations, consider adding extras like activities, car rentals and tours.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Evers Intl. Airport (JAN)?
Typically, it's possible to cancel or reschedule your MDW to JAN flight. However, for bookings made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Evers Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$236
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 November. 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 2025. You can also book with separate airlines for your outbound and return journeys, from $119 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

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*Available to One Key members.