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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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$287
(Southwest)

One-way from

$144
(Delta)

Popular in

March

Cheapest in

August

Average price

$346
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. 2% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Southwest deal was found by Cheapflights users on 2/19. 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 5/112:20 pmJAN - MDW
1 stop5h 50mSouthwest
Mon 5/55:10 amMDW - JAN
1 stop6h 25mSouthwest
Deal found 2/19$287
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2711:07 amJAN - MDW
1 stop5h 13mDelta
Sun 3/26:00 amMDW - JAN
1 stop5h 38mDelta
Deal found 2/20$527

Find flights from Jackson to Midway within your budget

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 February 20, 2025.

Fly from

Jackson

Fly to

Midway

Route

Depart

Return

Price

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 5/1

12:20 pm-6:10 pm

1 stop5h 50m

Chicago Midway

Mon 5/5

5:10 am-11:35 am

1 stop6h 25m

$287

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 3/6

11:07 am-4:20 pm

1 stop5h 13m

Chicago Midway

Mon 3/10

4:59 pm-11:03 pm

1 stop6h 04m

$559

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Mon 4/14

5:11 pm-10:26 pm

1 stop5h 15m

$144

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Mon 4/14

5:35 am-12:10 pm

2 stops6h 35m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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 February.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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 Jackson, Mississippi-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jackson, Mississippi-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

Travel insights for flights from Jackson to Midway

Get recent, data-driven insights about flights from Jackson to Midway including ideal travel times, pricing trends, and more.

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.

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 February 20, 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 February 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $287, 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 37% 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$517FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$338Average$396FlexibilityNo cancel feeOn-time63%
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