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$211+ Cheap flights from Midway (MDW) to Jackson, MS (JAN)

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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAN
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

This Delta deal was found by Cheapflights users on 1/25. 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.
Sat 2/144:13 pm
MDW
-
JAN
1 stop6h 54m
Delta
Mon 2/165:30 am
JAN
-
MDW
1 stop6h 29m
Delta
Deal found 1/25$309
This Delta deal was found by Cheapflights users on 1/26. 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 3/26:40 pm
MDW
-
JAN
1 stop4h 27m
Delta
Wed 4/15:35 am
JAN
-
MDW
1 stop6h 27m
Delta
Deal found 1/26$321
This Southwest deal was found by Cheapflights users on 1/25. 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 3/28:15 am
MDW
-
JAN
2 stops7h 25m
Southwest
Wed 4/15:50 am
JAN
-
MDW
1 stop4h 55m
Southwest
Deal found 1/25$326
This Southwest deal was found by Cheapflights users on 1/25. 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 3/116:25 am
MDW
-
JAN
1 stop5h 05m
Southwest
Sat 3/1412:20 pm
JAN
-
MDW
1 stop5h 30m
Southwest
Deal found 1/25$344
This Southwest deal was found by Cheapflights users on 1/25. 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 4/34:05 pm
MDW
-
JAN
1 stop3h 35m
Southwest
Tue 4/71:00 pm
JAN
-
MDW
1 stop7h 00m
Southwest
Deal found 1/25$349
This Southwest deal was found by Cheapflights users on 1/26. 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 2/2312:50 pm
MDW
-
JAN
2 stops8h 05m
Southwest
Mon 3/24:15 pm
JAN
-
MDW
1 stop5h 10m
Southwest
Deal found 1/26$355
This Delta deal was found by Cheapflights users on 1/26. 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 5/286:00 am
MDW
-
JAN
1 stop5h 20m
Delta
Sun 5/315:35 pm
JAN
-
MDW
1 stop4h 10m
Delta
Deal found 1/26$367
This Delta deal was found by Cheapflights users on 1/27. 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 2/1112:46 pm
MDW
-
JAN
1 stop6h 04m
Delta
Wed 2/1812:19 pm
JAN
-
MDW
1 stop5h 26m
Delta
Deal found 1/27$372
This Southwest deal was found by Cheapflights users on 1/26. 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 2/1112:20 pm
MDW
-
JAN
2 stops7h 40m
Southwest
Wed 2/181:25 pm
JAN
-
MDW
1 stop4h 40m
Southwest
Deal found 1/26$377
This Southwest deal was found by Cheapflights users on 1/26. 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 2/1112:20 pm
MDW
-
JAN
2 stops7h 40m
Southwest
Tue 2/175:35 am
JAN
-
MDW
2 stops8h 55m
Southwest
Deal found 1/26$382

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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$309
(Delta)

One-way from

$211
(Delta)

Popular in

January

Cheapest in

April

Average price

$616
Provider with most accurate pricing for Chicago Midway-Jackson-Evers Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Jackson-Evers Intl flights.
Search Deals
From Chicago Midway to Jackson-Evers Intl
Search Deals
One-way flight from Chicago Midway to Jackson-Evers Intl
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($72 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 January 2026
Search Deals

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 January 27, 2026.
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

Sat 2/14

4:13 pm-11:07 pm

1 stop6h 54m

Jackson-Evers Intl

Mon 2/16

5:30 am-11:59 am

1 stop6h 29m

$309

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Mon 3/2

4:10 pm-8:55 pm

1 stop4h 45m

Jackson-Evers Intl

Wed 4/1

5:50 am-10:45 am

1 stop4h 55m

$321

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Mon 3/2

6:00 am-10:10 am

1 stop4h 10m

Jackson-Evers Intl

Wed 4/1

5:35 am-12:02 pm

1 stop6h 27m

$321

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Mon 2/23

5:55 am-11:15 am

1 stop5h 20m

Jackson-Evers Intl

Mon 3/2

4:15 pm-9:25 pm

1 stop5h 10m

$321

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Thu 4/16

6:00 am-10:13 am

1 stop4h 13m

Jackson-Evers Intl

Sat 4/18

5:36 am-9:56 am

1 stop4h 20m

$321

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Tue 4/21

6:00 am-10:13 am

1 stop4h 13m

Jackson-Evers Intl

Sat 4/25

5:36 am-9:56 am

1 stop4h 20m

$321

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Tue 4/21

11:35 am-8:20 pm

2 stops8h 45m

Jackson-Evers Intl

Sat 4/25

6:10 pm-10:45 pm

1 stop4h 35m

$326

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Wed 3/11

6:00 am-12:07 pm

1 stop6h 07m

Jackson-Evers Intl

Sun 3/15

5:35 am-9:56 am

1 stop4h 21m

$344

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Wed 3/11

6:25 am-11:30 am

1 stop5h 05m

Jackson-Evers Intl

Sat 3/14

12:20 pm-11:00 pm

2 stops10h 40m

$355

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sun 2/15

6:00 am-11:34 am

1 stop5h 34m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 14 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 Chicago Midway Airport-Jackson, Mississippi flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Jackson, Mississippi flight deals on Cheapflights vs. FlightHub >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 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 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

How much does it cost to fly round-trip from Chicago Midway Airport to Jackson, Mississippi?

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 January 27, 2026.
See what other customers who have flown with Southwest 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
4,268 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

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
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

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 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 1 airline.

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

    Airlines like Delta and Southwest fly from Chicago Midway Airport to Jackson, Mississippi in about 4h 45m. The time it takes to get you to your destination can typically vary by up to 2h 09m. Chicago Midway Airport and Jackson, Mississippi are separated by a distance of 667 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Chicago Midway Airport to Jackson, Mississippi round-trip?

    According to our current data, Southwest ($316), offers the cheapest pricing from Chicago Midway Airport to Jackson, Mississippi. Users have found that Southwest is 28% 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 airline flying from Midway to Jackson

Discover the top airline 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$316Average$526FlexibilityNo cancel feeOn-time63%

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