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$119+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAN
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$237
(Delta)

One-way from

$119
(Delta)

Popular in

September

Cheapest in

April

Average price

$538
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. 14% potential increase in price ($71 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 July 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 July 29, 2025.

This Delta deal was found by Cheapflights users on 7/28. 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.
Tue 8/196:04 amMDW - JAN
1 stop6h 20mDelta
Sat 8/2310:00 amJAN - MDW
1 stop5h 28mDelta
Deal found 7/28$237
This Southwest deal was found by Cheapflights users on 7/29. 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.
Sat 8/237:40 amMDW - JAN
1 stop4h 50mSouthwest
Mon 8/256:35 pmJAN - MDW
1 stop5h 30mSouthwest
Deal found 7/29$259

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 July 29, 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 8/19

6:04 am-12:24 pm

1 stop6h 20m

Jackson-Evers Intl

Sat 8/23

10:00 am-3:28 pm

1 stop5h 28m

$237

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 8/23

7:40 am-12:30 pm

1 stop4h 50m

Jackson-Evers Intl

Mon 8/25

6:35 pm-12:05 am

1 stop5h 30m

$259

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 8/30

6:00 am-11:16 am

1 stop5h 16m

$119

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Wed 9/10

1:00 pm-8:05 pm

2 stops7h 05m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 $449). 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.

What’s the top layover airport for flights from Chicago Midway Airport to Jackson, Mississippi?

Share of 1-stop round-trip flights from Chicago Midway Airport to Jackson, Mississippi chosen by Cheapflights users in the past 12 months, using the same layover each way.

Nashville (BNA) – chosen by Cheapflights users on 83% of 1-stop itineraries from Chicago Midway Airport to Jackson, Mississippi on Cheapflights.

What’s the cheapest layover airport for flights from Chicago Midway Airport to Jackson, Mississippi?

Average round-trip fare for 1-stop flights from Chicago Midway Airport to Jackson, Mississippi, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Houston (HOU) is the most affordable 1-stop option, with an average round-trip price of $366.

What’s the fastest layover option from Chicago Midway Airport to Jackson, Mississippi?

Shortest average travel time for 1-stop one-way flights from Chicago Midway Airport to Jackson, Mississippi, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Houston (HOU) have the shortest average one-way travel time for 1-stop routes: 2h 45m.

Which airport typically offers the quickest layover for flights from Chicago Midway Airport to Jackson, Mississippi?

Average layover duration for 1-stop one-way flights from Chicago Midway Airport to Jackson, Mississippi, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Houston (HOU) offer the fastest connection on this route, with an average layover time of 1h 08m.

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 July 29, 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
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

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

    According to our current data, Delta ($237), and Southwest ($259) offers the cheapest pricing from Chicago Midway Airport to Jackson, Mississippi. Users have found that Delta is 44% 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 $449). 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$442FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$316Average$466FlexibilityNo cancel feeOn-time63%

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