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$144+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — MDW
Jun 28 — Jul 51
Sat 6/28
Sat 7/5
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 June 23, 2025.

Round-trip from

$266
(Southwest)

One-way from

$144
(Delta)

Popular in

January

Cheapest in

August

Average price

$324
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. 7% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($21 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 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 June 23, 2025.

This Southwest deal was found by Cheapflights users on 6/20. 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.
Sun 9/217:35 pmJAN - MDW
1 stop4h 50mSouthwest
Thu 9/255:45 amMDW - JAN
1 stop5h 35mSouthwest
Deal found 6/20$266
This Delta deal was found by Cheapflights users on 6/22. 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 8/67:43 amJAN - MDW
1 stop4h 15mDelta
Wed 8/136:04 amMDW - JAN
1 stop6h 20mDelta
Deal found 6/22$287

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 June 23, 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

Sun 9/21

7:35 pm-12:25 am

1 stop4h 50m

Chicago Midway

Thu 9/25

5:45 am-11:20 am

1 stop5h 35m

$266

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 8/6

7:43 am-11:58 am

1 stop4h 15m

Chicago Midway

Wed 8/13

6:04 am-12:24 pm

1 stop6h 20m

$287

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 8/5

5:50 am-9:45 am

1 stop3h 55m

$144

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 8/22

2:10 pm-7:50 pm

1 stop5h 40m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/21

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 June 23, 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.

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 23, 2025.
Get a feel of what it's like to fly with Southwest and Delta from Jackson to Chicago 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
4,278 reviews

Boarding

8.2

Entertainment

7.6

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

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
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Entertainment

7.6

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

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
7,966 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Entertainment

7.6

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

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 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.

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

    Southwest, at $266, was found to be the cheapest airline from Jackson, Mississippi to Chicago Midway Airport. An alternate airline flying to your destination would be Delta. Southwest is currently priced 34% 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 Jackson?

Book flights to Jackson if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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 June 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$386FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$346Average$396FlexibilityNo cancel feeOn-time63%

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