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$109+ 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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAN
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$262
(Southwest)

One-way from

$159
(Delta)

Popular in

September

Cheapest in

April

Average price

$448
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. 19% potential increase in price ($102 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/10. 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 10/25:30 amMDW - JAN
1 stop5h 50mSouthwest
Mon 10/68:05 pmJAN - MDW
1 stop4h 40mSouthwest
Deal found 6/10$257
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/212:43 pmMDW - JAN
1 stop6h 50mDelta
Wed 8/65:50 amJAN - MDW
1 stop3h 55mDelta
Deal found 6/10$287

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 June 12, 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

Thu 10/2

5:30 am-11:20 am

1 stop5h 50m

Jackson-Evers Intl

Mon 10/6

8:05 pm-12:45 am

1 stop4h 40m

$257

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 8/2

12:43 pm-7:33 pm

1 stop6h 50m

Jackson-Evers Intl

Wed 8/6

5:50 am-9:45 am

1 stop3h 55m

$287

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Thu 8/28

7:55 am-1:30 pm

1 stop5h 35m

$109

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Tue 7/8

6:00 am-10:05 am

1 stop4h 05m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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.

Rainfall in Jackson by month

Plan your trip to Jackson by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Jackson, Mississippi ranges from 2.2 - 5.6 inches per month. December is typically the wettest month, when rainfall can reach 5.6 in. October is typically the driest time to visit Jackson, Mississippi when rainfall is around 2.2 in.

Temperature in Jackson by month

Plan your trip to Jackson by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Jackson, Mississippi, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 48.2 F).

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 June 12, 2025.
Read through reviews of airlines operating flights from Chicago to Jackson, such as Southwest and Delta. 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
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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, Southwest ($262), and Delta ($287) offers the cheapest pricing from Chicago Midway Airport to Jackson, Mississippi. Users have found that Southwest is 38% 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Vicksburg
Pearl
Clinton
Flowood

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$452FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$316Average$436FlexibilityNo cancel feeOn-time63%

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