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$105+ Cheap flights from Jackson, MS (JAN) to Midway (MDW)

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

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

$217
(Delta)

One-way from

$105
(Delta)

Popular in

January

Cheapest in

August

Average price

$392
From Jackson-Evers Intl to Chicago Midway
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One-way flight from Jackson-Evers Intl to Chicago Midway
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Highest demand for flights based on searches. 5% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($20 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 Jackson to Midway

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

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.
Mon 12/86:03 pmJAN - MDW
1 stop5h 29mDelta
Tue 12/96:00 amMDW - JAN
1 stop4h 13mDelta
Deal found 9/11$217
This Southwest deal was found by Cheapflights users on 9/9. 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 11/113:40 pmJAN - MDW
1 stop5h 25mSouthwest
Fri 11/145:10 amMDW - JAN
1 stop6h 05mSouthwest
Deal found 9/9$239
This Southwest deal was found by Cheapflights users on 9/9. 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 10/28:05 pmJAN - MDW
1 stop4h 40mSouthwest
Sat 10/412:15 pmMDW - JAN
1 stop7h 40mSouthwest
Deal found 9/9$255
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 12/176:25 amJAN - MDW
2 stops8h 30mSouthwest
Thu 12/259:20 amMDW - JAN
1 stop8h 20mSouthwest
Deal found 9/10$295
This Delta deal was found by Cheapflights users on 9/9. 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.
Mon 11/107:16 pmJAN - MDW
1 stop4h 16mDelta
Tue 11/116:00 amMDW - JAN
1 stop5h 34mDelta
Deal found 9/9$299
This Southwest deal was found by Cheapflights users on 9/9. 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 9/2710:15 amJAN - MDW
1 stop4h 30mSouthwest
Tue 9/3011:45 amMDW - JAN
1 stop6h 25mSouthwest
Deal found 9/9$300

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jackson to Midway 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 Jackson to Chicago Midway Airport that are best for you.

Fly from

Jackson

Fly to

Midway

Route

Depart

Return

Price

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Mon 12/8

6:03 pm-11:32 pm

1 stop5h 29m

Chicago Midway

Tue 12/9

6:00 am-11:35 am

1 stop5h 35m

$217

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 10/17

8:05 pm-12:45 am

1 stop4h 40m

Chicago Midway

Mon 10/20

5:30 am-11:20 am

1 stop5h 50m

$335

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 9/26

3:10 pm-9:36 pm

1 stop6h 26m

Chicago Midway

Tue 9/30

6:30 pm-11:17 pm

1 stop4h 47m

$344

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 10/23

12:00 pm-7:00 pm

1 stop7h 00m

Chicago Midway

Sun 10/26

6:45 am-11:40 am

1 stop4h 55m

$384

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 10/16

8:05 pm-12:45 am

1 stop4h 40m

Chicago Midway

Mon 10/20

5:30 am-11:20 am

1 stop5h 50m

$387

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 10/16

5:35 am-12:40 pm

2 stops7h 05m

Chicago Midway

Sun 10/19

6:45 am-11:40 am

1 stop4h 55m

$394

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 10/16

5:58 pm-10:14 pm

1 stop4h 16m

Chicago Midway

Mon 10/20

12:48 pm-6:33 pm

1 stop5h 45m

$417

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 10/17

5:35 am-2:25 pm

2 stops8h 50m

Chicago Midway

Sun 10/19

7:50 am-2:15 pm

1 stop6h 25m

$453

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 10/9

8:05 pm-12:45 am

1 stop4h 40m

Chicago Midway

Thu 10/16

9:45 am-5:20 pm

2 stops7h 35m

$463

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 11/18

5:59 pm-11:32 pm

1 stop5h 33m

$105

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 18 results
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Best time to book a flight from Jackson to Midway

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

What is the cheapest time of day to fly from JAN to MDW?

Find hourly flight availability from Jackson to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

It’s typically best to fly out from Jackson, Mississippi to Chicago Midway Airport at noon. Doing so could potentially save you 23% on the flight price compared to flying in the morning, which is usually more expensive.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated September 11, 2025.
Get a feel of what it's like to fly with Southwest and Delta from Jackson to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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 Jackson to Midway. 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 from for flights from Jackson to Chicago Midway?

    Jackson-Evers Intl (JAN) is the airport you will fly out of if you book a flight from Jackson to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Jackson-Evers Intl; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 2 airlines have flights from the Jackson airport to Chicago Midway. It is only a 6.3 mi journey to Jackson-Evers Intl (JAN) from Jackson’s city center.

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

    Departing from Jackson, Mississippi to Chicago Midway Airport will take you 4h 40m. Jackson, Mississippi and Chicago Midway Airport are separated by a distance of 667 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Delta, at $196, was found to be the cheapest airline from Jackson, Mississippi to Chicago Midway Airport. An alternate airline flying to your destination would be Southwest. Delta is currently priced 52% below the average price you’ll pay for this route.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Jackson, Mississippi to Chicago Midway Airport (average of $160). Flying from Jackson, Mississippi to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top 2 airlines flying from Jackson to Midway

Discover the top 2 airlines that operate flights from Jackson to Midway. 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$196Average$356FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$234Average$378FlexibilityNo cancel feeOn-time63%

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