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$136+ Cheap flights from Midway (MDW) to Jackson, MS (JAN)

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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAN
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Midway to Jackson

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Jackson (JAN). 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 September 11, 2025.

Round-trip from

$206
(Southwest)

One-way from

$136
(Southwest)

Popular in

September

Cheapest in

April

Average price

$586
From Chicago Midway to Jackson-Evers Intl
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One-way flight from Chicago Midway to Jackson-Evers Intl
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Highest demand for flights based on searches. 10% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Jackson

Cheapest flights from Midway to Jackson
Explore the most affordable flight options available from Midway to Jackson. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/10. 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.
Tue 9/3011:45 amMDW - JAN
1 stop6h 25mSouthwest
Tue 10/76:30 amJAN - MDW
1 stop7h 05mSouthwest
Deal found 9/10$206
This Southwest deal was found by Cheapflights users on 9/10. 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 10/16:25 amMDW - JAN
1 stop6h 15mSouthwest
Fri 10/312:00 pmJAN - MDW
1 stop7h 00mSouthwest
Deal found 9/10$252
This Delta deal was found by Cheapflights users on 9/11. 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.
Thu 10/26:00 amMDW - JAN
1 stop6h 26mDelta
Sat 10/43:10 pmJAN - MDW
1 stop6h 00mDelta
Deal found 9/11$292
This Southwest deal was found by Cheapflights users on 9/11. 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.
Thu 10/211:25 amMDW - JAN
1 stop5h 55mSouthwest
Fri 10/312:00 pmJAN - MDW
1 stop7h 00mSouthwest
Deal found 9/11$303
This Southwest deal was found by Cheapflights users on 9/10. 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.
Thu 10/211:25 amMDW - JAN
1 stop5h 55mSouthwest
Sat 10/43:20 pmJAN - MDW
1 stop5h 00mSouthwest
Deal found 9/10$317
This Delta deal was found by Cheapflights users on 9/11. 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.
Fri 9/266:00 amMDW - JAN
1 stop4h 45mDelta
Tue 9/305:50 amJAN - MDW
1 stop3h 50mDelta
Deal found 9/11$318

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Jackson 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 September 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Jackson that are best for you.

Fly from

Midway

Fly to

Jackson

Route

Depart

Return

Price

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Tue 9/30

10:30 am-6:10 pm

2 stops7h 40m

Jackson-Evers Intl

Tue 10/7

7:05 pm-11:35 pm

1 stop4h 30m

$211

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Wed 10/1

6:25 am-12:40 pm

1 stop6h 15m

Jackson-Evers Intl

Fri 10/3

12:00 pm-7:00 pm

1 stop7h 00m

$252

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Thu 10/2

6:00 am-12:26 pm

1 stop6h 26m

Jackson-Evers Intl

Sat 10/4

3:10 pm-9:10 pm

1 stop6h 00m

$292

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Thu 10/2

11:25 am-5:20 pm

1 stop5h 55m

Jackson-Evers Intl

Fri 10/3

12:00 pm-7:00 pm

1 stop7h 00m

$303

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Fri 9/26

6:00 am-10:45 am

1 stop4h 45m

Jackson-Evers Intl

Tue 9/30

5:50 am-9:40 am

1 stop3h 50m

$318

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Thu 10/2

10:25 am-7:25 pm

2 stops9h 00m

Jackson-Evers Intl

Sat 10/4

3:20 pm-8:20 pm

1 stop5h 00m

$342

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Fri 11/7

9:30 am-2:30 pm

2 stops5h 00m

Jackson-Evers Intl

Sun 11/9

5:30 am-3:40 pm

2 stops10h 10m

$367

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Mon 10/27

5:30 am-11:20 am

1 stop5h 50m

$136

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Fri 9/26

1:40 pm-8:10 pm

1 stop6h 30m

$214

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sun 9/28

6:00 am-10:45 am

1 stop4h 45m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Best time to book a flight from Midway to Jackson

Have a flexible travel schedule? Discover the best time to fly to Jackson from Midway 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 Chicago Midway Airport to Jackson

What is the cheapest month to book a flight from Chicago Midway Airport to Jackson, Mississippi?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Jackson, Mississippi (average of $371). Flying from Chicago Midway Airport to Jackson, Mississippi in March is currently the most expensive (average of $448). 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.

Reviews of airlines servicing Jackson

Get insights into the airlines that provide service to Jackson. 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 Jackson. Reviews last updated September 11, 2025.
See what other customers who have flown with Southwest and Delta from Chicago Midway Airport to Jackson have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to Jackson. 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 into for flights to Jackson from Chicago Midway?

    Located just 6.3 mi from the city center, Jackson-Evers Intl is the airport most travelers will use when flying to Jackson from Chicago Midway. Booking flights from Chicago Midway to Jackson-Evers Intl (JAN) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 2 different airlines.

  • How long is the flight from Chicago Midway Airport to Jackson, Mississippi?

    Airlines like Southwest and Delta fly from Chicago Midway Airport to Jackson, Mississippi in about 6h 26m. The time it takes to get you to your destination can typically vary by up to 1h 14m. Chicago Midway Airport and Jackson, Mississippi are separated by a distance of 667 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago Midway Airport to Jackson, Mississippi round-trip?

    According to our current data, Delta ($248), and Southwest ($316) offers the cheapest pricing from Chicago Midway Airport to Jackson, Mississippi. Users have found that Delta is 40% cheaper than the other options available to this destination.

  • Can I find deals for flights from Midway to Jackson that include hotel bookings?

    Yes. In addition to deals on Midway to Jackson flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Jackson?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Jackson.

  • Can I find deals for business class flights from Midway to Jackson?

    Yes. Cheapflights offers flight deals from Midway to Jackson 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 Chicago Midway Airport to Jackson, Mississippi?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Jackson, Mississippi (average of $371). Flying from Chicago Midway Airport to Jackson, Mississippi in March is currently the most expensive (average of $448). 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
Vicksburg
Clinton
Flowood
Pearl

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Top 2 airlines flying from Midway to Jackson

Discover the top 2 airlines that operate flights from Midway to Jackson. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$442FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$316Average$464FlexibilityNo cancel feeOn-time63%

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