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Midway

$149+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — MDW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This Southwest deal was found by Cheapflights users on 12/9. 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.
Mon 12/298:25 pmJAN - MDW
1 stop4h 45mSouthwest
Sun 1/45:05 amMDW - JAN
1 stop6h 00mSouthwest
Deal found 12/9$444
This Southwest deal was found by Cheapflights users on 12/9. 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 12/238:25 pmJAN - MDW
1 stop4h 45mSouthwest
Sun 12/288:40 amMDW - JAN
2 stops8h 50mSouthwest
Deal found 12/9$488
This Southwest deal was found by Cheapflights users on 12/9. 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.
Fri 12/268:25 pmJAN - MDW
1 stop4h 45mSouthwest
Sun 12/288:40 amMDW - JAN
2 stops8h 50mSouthwest
Deal found 12/9$498
This Delta deal was found by Cheapflights users on 12/10. 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.
Thu 12/1111:17 amJAN - MDW
1 stop5h 01mDelta
Thu 1/156:45 amMDW - JAN
1 stop7h 21mDelta
Deal found 12/10$565
This Southwest deal was found by Cheapflights users on 12/10. 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.
Fri 12/1911:40 amJAN - MDW
1 stop6h 15mSouthwest
Sun 12/212:50 pmMDW - JAN
1 stop7h 15mSouthwest
Deal found 12/10$577

Find 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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$297
(Delta)

One-way from

$149
(Delta)

Popular in

January

Cheapest in

August

Average price

$467
Provider with most accurate pricing for Jackson-Evers Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Jackson-Evers Intl-Chicago Midway flights.
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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. 11% potential increase in price ($55 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 12, 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

Thu 1/8

9:28 am-4:29 pm

1 stop7h 01m

Chicago Midway

Thu 1/15

6:45 am-11:17 am

1 stop4h 32m

$314

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 2/6

4:15 pm-9:25 pm

1 stop5h 10m

Chicago Midway

Sun 2/8

10:05 am-2:40 pm

1 stop4h 35m

$367

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 1/9

4:58 pm-10:07 pm

1 stop5h 09m

Chicago Midway

Fri 1/16

6:45 am-11:17 am

1 stop4h 32m

$377

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 1/9

6:40 am-1:30 pm

1 stop6h 50m

Chicago Midway

Fri 1/16

10:45 am-6:05 pm

1 stop7h 20m

$387

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Mon 12/29

8:25 pm-1:10 am

1 stop4h 45m

Chicago Midway

Sun 1/4

5:05 am-11:05 am

1 stop6h 00m

$444

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 12/23

8:25 pm-1:10 am

1 stop4h 45m

Chicago Midway

Sun 12/28

8:40 am-5:30 pm

2 stops8h 50m

$488

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 12/26

8:25 pm-1:10 am

1 stop4h 45m

Chicago Midway

Sun 12/28

1:20 pm-7:45 pm

1 stop6h 25m

$522

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sat 1/24

5:32 am-9:53 am

1 stop4h 21m

$149

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sat 1/10

4:30 pm-10:07 pm

1 stop5h 37m

$149

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sat 1/10

1:15 pm-5:20 pm

1 stop4h 05m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 16 results
1
2

Compare providers for flights from Jackson to Midway

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 Jackson to Midway in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust 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 Jackson, Mississippi-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Jackson, Mississippi-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Jackson, Mississippi-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Jackson, Mississippi-Chicago Midway Airport 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 Jackson, Mississippi-Chicago Midway Airport 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 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 December 12, 2025.

It’s typically best to fly out from Jackson, Mississippi to Chicago Midway Airport in the afternoon. Doing so could potentially save you 22% 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 December 12, 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
7.9
Good
4,253 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

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
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

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
8,008 reviews
Southwest
7.9
Good
4,253 reviews

Boarding

8.1

Overall

7.9

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

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 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 5h 10m. 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 53% 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.

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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$196Average$350FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$234Average$392FlexibilityNo cancel feeOn-time63%

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