HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$161+ 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 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — MDW
feb. 26 — mar. 51
jue. 2/26
jue. 3/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Jackson to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 enero 27, 2026.

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.
mar. 2/174:15 pm
JAN
-
MDW
1 stop5h 10m
Southwest
jue. 2/1910:45 am
MDW
-
JAN
1 stop7h 20m
Southwest
Deal found 1/25$309
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.
mar. 5/55:02 pm
JAN
-
MDW
1 stop5h 26m
Delta
mar. 5/126:00 am
MDW
-
JAN
1 stop4h 02m
Delta
Deal found 1/27$321
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.
sáb. 2/216:05 am
JAN
-
MDW
2 stops9h 40m
Southwest
lun. 2/235:55 am
MDW
-
JAN
1 stop5h 20m
Southwest
Deal found 1/26$326
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.
dom. 2/225:30 am
JAN
-
MDW
1 stop4h 24m
Delta
mar. 2/246:00 am
MDW
-
JAN
1 stop4h 10m
Delta
Deal found 1/26$342
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.
dom. 2/224:50 pm
JAN
-
MDW
1 stop5h 55m
Southwest
mar. 2/246:10 am
MDW
-
JAN
2 stops8h 30m
Southwest
Deal found 1/26$357
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.
vie. 4/1010:55 am
JAN
-
MDW
1 stop6h 27m
Delta
dom. 4/126:00 am
MDW
-
JAN
1 stop6h 07m
Delta
Deal found 1/26$367
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.
jue. 3/1212:20 pm
JAN
-
MDW
1 stop5h 20m
Southwest
lun. 3/164:05 pm
MDW
-
JAN
1 stop3h 35m
Southwest
Deal found 1/26$371

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 enero 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$309
(Southwest)

One-way from

$161
(Delta)

Popular in

January

Cheapest in

August

Average price

$616
Provider with most accurate pricing for Jackson-Evers Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jackson-Evers Intl-Chicago Midway flights.
Search Deals
From Jackson-Evers Intl to Chicago Midway
Search Deals
One-way flight from Jackson-Evers Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($55 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 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 enero 27, 2026.
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

mar. 2/17

4:15 pm-9:25 pm

1 stop5h 10m

Chicago Midway

jue. 2/19

10:45 am-6:05 pm

1 stop7h 20m

$309

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

sáb. 4/11

5:35 am-9:56 am

1 stop4h 21m

Chicago Midway

lun. 4/13

6:00 am-10:13 am

1 stop4h 13m

$321

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

sáb. 2/21

12:25 pm-6:50 pm

1 stop6h 25m

Chicago Midway

lun. 2/23

5:55 am-11:15 am

1 stop5h 20m

$321

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

mar. 5/5

5:02 pm-10:28 pm

1 stop5h 26m

Chicago Midway

mar. 5/12

6:00 am-11:20 am

1 stop5h 20m

$321

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

dom. 2/22

5:30 am-9:54 am

1 stop4h 24m

Chicago Midway

mar. 2/24

6:00 am-10:10 am

1 stop4h 10m

$342

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

dom. 2/22

4:50 pm-10:45 pm

1 stop5h 55m

Chicago Midway

mar. 2/24

6:10 am-2:40 pm

2 stops8h 30m

$357

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

vie. 4/10

10:55 am-5:22 pm

1 stop6h 27m

Chicago Midway

dom. 4/12

6:00 am-12:07 pm

1 stop6h 07m

$367

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

sáb. 5/23

2:40 pm-9:45 pm

1 stop7h 05m

Chicago Midway

lun. 5/25

6:00 am-11:20 am

1 stop5h 20m

$367

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

mar. 3/31

5:35 am-9:56 am

1 stop4h 21m

$161

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

mar. 3/31

12:05 pm-7:55 pm

2 stops7h 50m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 19 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 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 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.

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 enero 27, 2026.
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
4,268 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

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

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

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
8,119 reviews
Southwest
8.0
Very good
4,268 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

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 4h 21m. 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 enero 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$196Average$350FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$234Average$392FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.