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

View $99 flight on Wed, Dec 10, 2025Opens in a new window

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

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Cheap Flights from Jackson to Chicago (JAN-MDW)

Prices were available within the past 7 days and start at $99 for one-way flights and $255 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Dec 15 - Tue, Jan 6
JAN
Jackson
MDW
Chicago
$255 Roundtrip, found 6 days ago
$255
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Dec 15 from Jackson to Chicago, returning Tue, Jan 6, priced at $255 found 6 days ago
Southwest Airlines
Mon, Dec 15 - Wed, Dec 17
JAN
Jackson
MDW
Chicago
$255 Roundtrip, found 6 days ago
$255
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, Dec 15 from Jackson to Chicago, returning Wed, Dec 17, priced at $255 found 6 days ago
Southwest Airlines
Mon, Dec 15 - Wed, Dec 17
JAN
Jackson
MDW
Chicago
$261 Roundtrip, found 6 days ago
$261
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, Dec 15 from Jackson to Chicago, returning Wed, Dec 17, priced at $261 found 6 days ago
Delta
Thu, Nov 27 - Tue, Dec 2
JAN
Jackson
MDW
Chicago
$272 Roundtrip, found 2 days ago
$272
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Nov 27 from Jackson to Chicago, returning Tue, Dec 2, priced at $272 found 2 days ago
Delta
Wed, Dec 24 - Tue, Jan 6
JAN
Jackson
MDW
Chicago
$277 Roundtrip, found 5 days ago
$277
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Dec 24 from Jackson to Chicago, returning Tue, Jan 6, priced at $277 found 5 days ago
Southwest Airlines
Mon, Dec 15 - Wed, Dec 17
JAN
Jackson
MDW
Chicago
$280 Roundtrip, found 6 days ago
$280
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, Dec 15 from Jackson to Chicago, returning Wed, Dec 17, priced at $280 found 6 days ago
Delta
Mon, Nov 24 - Tue, Dec 9
JAN
Jackson
MDW
Chicago
$282 Roundtrip, found 10 hours ago
$282
Roundtrip
found 10 hours ago
Select Delta flight, departing Mon, Nov 24 from Jackson to Chicago, returning Tue, Dec 9, priced at $282 found 10 hours ago
Southwest Airlines
Wed, Dec 17 - Sat, Dec 20
JAN
Jackson
MDW
Chicago
$283 Roundtrip, found 6 days ago
$283
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Dec 17 from Jackson to Chicago, returning Sat, Dec 20, priced at $283 found 6 days ago
Delta
Wed, Dec 24 - Mon, Jan 5
JAN
Jackson
MDW
Chicago
$283 Roundtrip, found 5 days ago
$283
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Dec 24 from Jackson to Chicago, returning Mon, Jan 5, priced at $283 found 5 days ago
Southwest Airlines
Mon, Dec 15 - Wed, Dec 17
JAN
Jackson
MDW
Chicago
$285 Roundtrip, found 6 days ago
$285
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, Dec 15 from Jackson to Chicago, returning Wed, Dec 17, priced at $285 found 6 days ago

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

September is typically the cheapest month to fly

From $207 - $548 per traveler.

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Average driving time to city center is 23 minutes. Flights from $447
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $447

Frequently asked questions

How much does a flight from Evers Intl. Airport (JAN) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $99 or cheap return flight from $255 from Evers Intl. Airport (JAN) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Evers Intl. Airport (JAN) to Midway Intl. Airport (MDW)?
December is the least expensive month to fly from JAN to MDW. Timing your trip outside of the busy season is often the key to finding a great deal.
What is the cheapest airline that flies from Evers Intl. Airport (JAN) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare airlines and find the most affordable carrier that'll take you from JAN to MDW. Then, sort your results by "Price (lowest to highest)" to score the best deal available.
How many flights per day from Evers Intl. Airport (JAN) to Midway Intl. Airport (MDW)?
Direct flights from Evers Intl. Airport (JAN) to Midway Intl. Airport (MDW) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from JAN to MDW?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Remember that flight schedules can vary based on a range of factors, such as the airline and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Evers Intl. Airport (JAN) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Evers Intl. Airport (JAN) to Midway Intl. Airport (MDW) route, travel before 3 PM. Departures after this time have a 22% higher chance of being canceled.**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 Evers Intl. Airport (JAN) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from JAN to MDW right before your trip is usually more expensive. But if there's some wiggle room with your departure dates and times, you could land a cheap last-minute fare.
Is it cheaper to book a JAN to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a JAN to MDW flight and hotel package with Expedia could result in significant savings. Better still, having everything in one place takes the hassle out of planning your trip. Simply secure your flights and select from our wide range of stays, then tailor your trip with other add-ons like tours and car rentals.
Can I cancel or change the date of my flight from Evers Intl. Airport (JAN) to Midway Intl. Airport (MDW)?
If you booked your JAN to MDW flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of fare you have, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for further details.

Travel information

Origin airport
Evers Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$254
Distance
667 mi

Book with confidence

Jackson to Chicago Flights

The cheapest times to fly from Jackson to Chicago

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 Jackson to Chicago are during the month of December. You can find some of the cheapest flights from Jackson to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Jackson to Chicago

Sunday is one of the best days to book for cheap flights from Jackson to Chicago: 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 Jackson to Chicago

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 Jackson to Chicago 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 Jackson to Chicago 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 Jackson to Chicago 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.

 

Jackson to Chicago Flights

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*Available to One Key members.