$99 Cheap Flights from Chicago (MDW) to Jackson (JAN)

View $99 flight on Tue, Dec 16, 2025Opens in a new window

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

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Cheap Flights from Chicago to Jackson (MDW-JAN)

Prices were available within the past 7 days and start at $99 for one-way flights and $235 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Dec 4 - Tue, Dec 9
MDW
Chicago
JAN
Jackson
$235 Roundtrip, found 9 hours ago
$235
Roundtrip
found 9 hours ago
Select Delta flight, departing Thu, Dec 4 from Chicago to Jackson, returning Tue, Dec 9, priced at $235 found 9 hours ago
Southwest Airlines
Sat, Dec 6 - Mon, Jan 12
MDW
Chicago
JAN
Jackson
$235 Roundtrip, found 7 hours ago
$235
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sat, Dec 6 from Chicago to Jackson, returning Mon, Jan 12, priced at $235 found 7 hours ago
Delta
Wed, Jan 21 - Tue, Jan 27
MDW
Chicago
JAN
Jackson
$239 Roundtrip, found 19 hours ago
$239
Roundtrip
found 19 hours ago
Select Delta flight, departing Wed, Jan 21 from Chicago to Jackson, returning Tue, Jan 27, priced at $239 found 19 hours ago
Southwest Airlines
Sat, Dec 6 - Mon, Jan 12
MDW
Chicago
JAN
Jackson
$240 Roundtrip, found 7 hours ago
$240
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sat, Dec 6 from Chicago to Jackson, returning Mon, Jan 12, priced at $240 found 7 hours ago
Delta
Wed, Jan 7 - Sun, Jan 18
MDW
Chicago
JAN
Jackson
$243 Roundtrip, found 1 day ago
$243
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jan 7 from Chicago to Jackson, returning Sun, Jan 18, priced at $243 found 1 day ago
Southwest Airlines
Thu, Dec 4 - Tue, Dec 9
MDW
Chicago
JAN
Jackson
$246 Roundtrip, found 9 hours ago
$246
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Thu, Dec 4 from Chicago to Jackson, returning Tue, Dec 9, priced at $246 found 9 hours ago
Southwest Airlines
Sat, Dec 6 - Mon, Jan 12
MDW
Chicago
JAN
Jackson
$248 Roundtrip, found 7 hours ago
$248
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sat, Dec 6 from Chicago to Jackson, returning Mon, Jan 12, priced at $248 found 7 hours ago
Southwest Airlines
Sat, Dec 6 - Mon, Jan 12
MDW
Chicago
JAN
Jackson
$253 Roundtrip, found 7 hours ago
$253
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Sat, Dec 6 from Chicago to Jackson, returning Mon, Jan 12, priced at $253 found 7 hours ago
Delta
Sat, Dec 6 - Mon, Jan 12
MDW
Chicago
JAN
Jackson
$255 Roundtrip, found 7 hours ago
$255
Roundtrip
found 7 hours ago
Select Delta flight, departing Sat, Dec 6 from Chicago to Jackson, returning Mon, Jan 12, priced at $255 found 7 hours ago
Delta
Mon, Dec 8 - Sat, Dec 13
MDW
Chicago
JAN
Jackson
$255 Roundtrip, found 9 hours ago
$255
Roundtrip
found 9 hours ago
Select Delta flight, departing Mon, Dec 8 from Chicago to Jackson, returning Sat, Dec 13, priced at $255 found 9 hours 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 $362
JAN
Evers Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $362

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 $99 or cheap return flight from $235 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 December 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
$234
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 December. 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 $99 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.