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$174+ Cheap flights from Midway (MDW) to Jackson, MS (JAN)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAN
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Cheap 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 December 4, 2025.

This Southwest deal was found by Cheapflights users on 12/2. 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 12/3011:45 amMDW - JAN
1 stop5h 45mSouthwest
Tue 1/61:25 pmJAN - MDW
1 stop4h 40mSouthwest
Deal found 12/2$290
This Delta deal was found by Cheapflights users on 12/2. 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 12/1612:50 pmMDW - JAN
1 stop4h 31mDelta
Wed 12/175:48 amJAN - MDW
1 stop6h 07mDelta
Deal found 12/2$297
This Southwest deal was found by Cheapflights users on 12/2. 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 12/167:00 amMDW - JAN
1 stop5h 25mSouthwest
Wed 12/176:25 amJAN - MDW
2 stops9h 30mSouthwest
Deal found 12/2$337
This Delta deal was found by Cheapflights users on 12/1. 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 12/176:00 amMDW - JAN
1 stop5h 30mDelta
Sun 12/215:32 pmJAN - MDW
1 stop4h 50mDelta
Deal found 12/1$372
This Southwest deal was found by Cheapflights users on 12/2. 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 12/245:35 amMDW - JAN
1 stop9h 30mSouthwest
Tue 12/308:25 pmJAN - MDW
1 stop4h 45mSouthwest
Deal found 12/2$399
This Southwest deal was found by Cheapflights users on 12/2. 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 12/245:35 amMDW - JAN
1 stop9h 30mSouthwest
Mon 12/298:25 pmJAN - MDW
1 stop4h 45mSouthwest
Deal found 12/2$412
This Delta deal was found by Cheapflights users on 12/3. 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 12/259:50 amMDW - JAN
1 stop7h 02mDelta
Mon 12/295:32 pmJAN - MDW
1 stop4h 50mDelta
Deal found 12/3$421
This Southwest deal was found by Cheapflights users on 12/2. 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 12/235:00 amMDW - JAN
1 stop6h 05mSouthwest
Tue 12/308:25 pmJAN - MDW
1 stop4h 45mSouthwest
Deal found 12/2$444
This Delta deal was found by Cheapflights users on 12/3. 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 12/1812:45 pmMDW - JAN
1 stop5h 44mDelta
Mon 12/225:32 pmJAN - MDW
1 stop4h 50mDelta
Deal found 12/3$447

Find 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 December 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$174
(Southwest)

Popular in

January

Cheapest in

May

Average price

$419
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.
Search Deals
From Chicago Midway to Jackson-Evers Intl
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 4, 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

Mon 1/12

6:50 am-2:40 pm

2 stops7h 50m

Jackson-Evers Intl

Wed 1/14

6:10 pm-10:55 pm

1 stop4h 45m

$225

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Tue 2/10

6:00 am-11:22 am

1 stop5h 22m

Jackson-Evers Intl

Sat 2/14

5:30 am-4:14 pm

2 stops10h 44m

$243

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Thu 1/15

6:45 am-11:17 am

1 stop4h 32m

Jackson-Evers Intl

Sun 1/18

5:32 am-10:27 am

1 stop4h 55m

$260

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Tue 12/30

11:45 am-5:30 pm

1 stop5h 45m

Jackson-Evers Intl

Tue 1/6

1:25 pm-6:05 pm

1 stop4h 40m

$290

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Tue 12/16

12:50 pm-5:21 pm

1 stop4h 31m

Jackson-Evers Intl

Wed 12/17

5:48 am-11:55 am

1 stop6h 07m

$297

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Thu 1/15

8:15 am-3:40 pm

2 stops7h 25m

Jackson-Evers Intl

Sun 1/18

1:25 pm-6:05 pm

1 stop4h 40m

$345

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Wed 12/17

6:00 am-11:30 am

1 stop5h 30m

Jackson-Evers Intl

Sun 12/21

5:32 pm-10:22 pm

1 stop4h 50m

$372

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Wed 12/24

5:35 am-3:05 pm

1 stop9h 30m

Jackson-Evers Intl

Tue 12/30

8:25 pm-1:10 am

1 stop4h 45m

$399

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Thu 12/25

9:50 am-4:52 pm

1 stop7h 02m

Jackson-Evers Intl

Mon 12/29

5:32 pm-10:22 pm

1 stop4h 50m

$421

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Fri 1/2

6:00 am-11:18 am

1 stop5h 18m

$184

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 13 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 December.
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 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 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 December 4, 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
4,250 reviews

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,011 reviews
Southwest
8.0
Very good
4,250 reviews

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 22m. The time it takes to get you to your destination can typically vary by up to 2h 28m. 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 ($149), and Southwest ($316) offers the cheapest pricing from Chicago Midway Airport to Jackson, Mississippi. Users have found that Delta is 66% 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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$456FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$316Average$476FlexibilityNo cancel feeOn-time63%

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