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$184+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAN
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$272
(Southwest)

One-way from

$184
(Delta)

Popular in

July

Cheapest in

May

Average price

$482
Provider with most accurate pricing for Chicago Midway-Jackson-Evers Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Jackson-Evers Intl flights.
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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. 5% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 28, 2025.

This Southwest deal was found by Cheapflights users on 10/27. 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 12/182:20 pmMDW - JAN
1 stop5h 15mSouthwest
Wed 12/313:40 pmJAN - MDW
1 stop5h 25mSouthwest
Deal found 10/27$272
This Delta deal was found by Cheapflights users on 10/25. 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 11/156:00 amMDW - JAN
1 stop5h 34mDelta
Sat 11/155:59 pmJAN - MDW
1 stop5h 41mDelta
Deal found 10/25$297
This Southwest deal was found by Cheapflights users on 10/27. 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 12/35:00 amMDW - JAN
2 stops7h 25mSouthwest
Wed 12/33:40 pmJAN - MDW
1 stop5h 25mSouthwest
Deal found 10/27$302
This Southwest deal was found by Cheapflights users on 10/27. 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 11/197:00 amMDW - JAN
1 stop5h 25mSouthwest
Sat 11/225:10 pmJAN - MDW
1 stop6h 10mSouthwest
Deal found 10/27$342
This Southwest deal was found by Cheapflights users on 10/26. 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.
Fri 11/215:10 amMDW - JAN
1 stop6h 05mSouthwest
Mon 11/243:05 pmJAN - MDW
1 stop3h 35mSouthwest
Deal found 10/26$372
This Delta deal was found by Cheapflights users on 10/27. 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 11/255:34 pmMDW - JAN
1 stop5h 29mDelta
Mon 12/17:16 pmJAN - MDW
1 stop4h 24mDelta
Deal found 10/27$377
This Southwest deal was found by Cheapflights users on 10/26. 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 11/255:00 amMDW - JAN
1 stop6h 05mSouthwest
Tue 12/21:10 pmJAN - MDW
1 stop9h 25mSouthwest
Deal found 10/26$388
This Delta deal was found by Cheapflights users on 10/27. 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.
Wed 11/126:00 amMDW - JAN
1 stop5h 34mDelta
Mon 11/177:16 pmJAN - MDW
1 stop4h 24mDelta
Deal found 10/27$407

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 October 28, 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 12/18

2:20 pm-7:35 pm

1 stop5h 15m

Jackson-Evers Intl

Wed 12/31

3:40 pm-9:05 pm

1 stop5h 25m

$272

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 11/15

6:00 am-11:34 am

1 stop5h 34m

Jackson-Evers Intl

Sat 11/15

5:59 pm-11:40 pm

1 stop5h 41m

$297

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Tue 11/25

5:34 pm-11:03 pm

1 stop5h 29m

Jackson-Evers Intl

Tue 12/2

6:06 pm-11:47 pm

1 stop5h 41m

$342

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Wed 11/19

5:35 am-12:25 pm

2 stops6h 50m

Jackson-Evers Intl

Sat 11/22

5:10 pm-11:20 pm

1 stop6h 10m

$368

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Fri 11/21

5:10 am-11:15 am

1 stop6h 05m

Jackson-Evers Intl

Mon 11/24

3:05 pm-6:40 pm

1 stop3h 35m

$372

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Tue 11/25

5:34 pm-11:03 pm

1 stop5h 29m

Jackson-Evers Intl

Mon 12/1

7:16 pm-11:40 pm

1 stop4h 24m

$377

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Wed 11/12

6:00 am-11:34 am

1 stop5h 34m

Jackson-Evers Intl

Mon 11/17

7:16 pm-11:40 pm

1 stop4h 24m

$407

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 11/15

6:00 am-11:34 am

1 stop5h 34m

Jackson-Evers Intl

Sun 11/16

7:16 pm-11:40 pm

1 stop4h 24m

$417

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 11/15

5:00 am-12:25 pm

1 stop7h 25m

Jackson-Evers Intl

Sun 11/16

11:50 am-8:30 pm

2 stops8h 40m

$422

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Fri 11/14

11:00 am-2:30 pm

1 stop3h 30m

Jackson-Evers Intl

Sun 11/16

11:50 am-8:30 pm

2 stops8h 40m

$422

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 14 results
1
2

Compare providers for flights from Midway to Jackson

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Jackson in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Jackson, Mississippi flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Jackson, Mississippi flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Jackson, Mississippi flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Jackson, Mississippi flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Jackson, Mississippi flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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’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 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 Nashville (BNA) have the shortest average one-way travel time for 1-stop routes: 4h 55m.

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 Nashville (BNA) have the shortest average one-way travel time for 1-stop routes: 4h 55m.

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 October 28, 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
4,240 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

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
7.9
Good
7,994 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

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 5h 15m. The time it takes to get you to your destination can typically vary by up to 19m. 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.

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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$452FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$316Average$466FlexibilityNo cancel feeOn-time63%

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