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 32m. The time it takes to get you to your destination can typically vary by up to 48m. Chicago Midway Airport and Jackson, Mississippi are separated by a distance of 667 mi. This flight may include one or multiple stops.

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

According to our current data, Delta ($149), and Southwest ($316) offers the cheapest pricing from Chicago Midway Airport to Jackson, Mississippi. Users have found that Delta is 65% cheaper than the other options available to this destination.

In terms of precipitation, rainfall in Jackson, Mississippi ranges from 2.2 - 5.6 inches per month. December is typically the wettest month, when rainfall can reach 5.6 in. October is typically the driest time to visit Jackson, Mississippi when rainfall is around 2.2 in.

If weather is an important factor for your trip to Jackson, Mississippi, 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 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 48.2 F).

What is the cheapest time of day to fly from MDW to JAN?

When flying from Chicago Midway Airport to Jackson, Mississippi, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Most accurate provider : When it comes to deals on Chicago Midway Airport-Jackson, Mississippi flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Jackson, Mississippi flight deals on Cheapflights vs. eDreams >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 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 Chicago Midway Airport-Jackson, Mississippi flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 2 different airlines.

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.

$163+ Flights from Chicago Midway Airport to Jackson, MS

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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 December 12, 2025.

Wed 12/316:40 amMDW - JAN

1 stop11h 00mSouthwest

Thu 1/86:40 amJAN - MDW

1 stop6h 50mSouthwest

Deal found 12/10

$295

Fri 12/265:00 amMDW - JAN

1 stop6h 05mSouthwest

Wed 12/313:40 pmJAN - MDW

1 stop5h 25mSouthwest

Deal found 12/10

$396

Tue 12/301:20 pmMDW - JAN

1 stop6h 25mSouthwest

Fri 1/28:25 pmJAN - MDW

1 stop4h 45mSouthwest

Deal found 12/10

$438

Fri 12/265:00 amMDW - JAN

1 stop6h 05mSouthwest

Tue 12/308:25 pmJAN - MDW

1 stop4h 45mSouthwest

Deal found 12/11

$467

Mon 12/225:00 amMDW - JAN

1 stop6h 05mSouthwest

Mon 12/298:25 pmJAN - MDW

1 stop4h 45mSouthwest

Deal found 12/11

$512

Best flights from Midway to Jackson
Discover carefully curated flight deals from Midway to Jackson that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 12, 2025.

Sun 1/186:45 amMDW - JAN

1 stop4h 32mDelta

Sun 1/184:30 pmJAN - MDW

1 stop5h 37mDelta

Deal found 12/10

$279

Tue 2/175:55 amMDW - JAN

1 stop5h 20mSouthwest

Thu 2/1911:50 amJAN - MDW

1 stop6h 20mSouthwest

Deal found 12/9

$311

Fri 1/166:45 amMDW - JAN

1 stop4h 32mDelta

Sun 1/184:30 pmJAN - MDW

1 stop5h 37mDelta

Deal found 12/10

$311

Fri 2/65:55 amMDW - JAN

1 stop5h 20mSouthwest

Sun 2/86:40 amJAN - MDW

1 stop6h 50mSouthwest

Deal found 12/9

$367

Wed 12/3110:50 amMDW - JAN

2 stops9h 05mSouthwest

Thu 1/86:40 amJAN - MDW

2 stops9h 50mSouthwest

Deal found 12/10

$383

Sun 3/82:10 pmMDW - JAN

1 stop5h 10mSouthwest

Fri 3/135:30 amJAN - MDW

2 stops9h 50mSouthwest

Deal found 12/11

$392

Fri 12/265:00 amMDW - JAN

1 stop6h 05mSouthwest

Wed 12/313:40 pmJAN - MDW

1 stop5h 25mSouthwest

Deal found 12/10

$396

Fri 1/1610:45 amMDW - JAN

1 stop7h 20mSouthwest

Sun 1/181:25 pmJAN - MDW

1 stop4h 40mSouthwest

Deal found 12/10

$401

Fri 1/25:00 amMDW - JAN

1 stop6h 05mSouthwest

Sun 1/46:05 pmJAN - MDW

1 stop5h 00mSouthwest

Deal found 12/10

$404

Last-minute flights from Midway to Jackson
Discover last-minute flight deals from Midway to Jackson. Data last updated December 12, 2025 and is based on user searches.

Fri 12/265:00 amMDW - JAN

1 stop6h 05mSouthwest

Wed 12/313:40 pmJAN - MDW

1 stop5h 25mSouthwest

Deal found 12/10

$396

Tue 12/301:20 pmMDW - JAN

1 stop6h 25mSouthwest

Fri 1/28:25 pmJAN - MDW

1 stop4h 45mSouthwest

Deal found 12/10

$438

Wed 12/316:40 amMDW - JAN

1 stop11h 00mSouthwest

Thu 1/86:40 amJAN - MDW

1 stop6h 50mSouthwest

Deal found 12/10

$295

Fri 1/25:00 amMDW - JAN

1 stop6h 05mSouthwest

Sun 1/46:05 pmJAN - MDW

1 stop5h 00mSouthwest

Deal found 12/10

$404

Fri 1/166:45 amMDW - JAN

1 stop4h 32mDelta

Sun 1/184:30 pmJAN - MDW

1 stop5h 37mDelta

Deal found 12/10

$311

Fri 1/1610:45 amMDW - JAN

1 stop7h 20mSouthwest

Sun 1/181:25 pmJAN - MDW

1 stop4h 40mSouthwest

Deal found 12/10

$401

Sun 1/186:45 amMDW - JAN

1 stop4h 32mDelta

Sun 1/184:30 pmJAN - MDW

1 stop5h 37mDelta

Deal found 12/10

$279

Sun 1/186:10 amMDW - JAN

2 stops8h 30mSouthwest

Sun 1/186:10 pmJAN - MDW

1 stop4h 45mSouthwest

Deal found 12/10

$417

One-way flights from Midway to Jackson
Search for one-way flight options from Midway to Jackson. Find affordable one-way fares based on user searches. Data last updated December 12, 2025.

Thu 1/86:45 amMDW - JAN

1 stop4h 32mDelta

Deal found 12/10

$163

Thu 1/86:50 amMDW - JAN

2 stops7h 50mSouthwest

Deal found 12/10

$168

Mon 12/295:00 amMDW - JAN

1 stop6h 05mSouthwest

Deal found 12/11

$270

Fri 12/1910:49 amMDW - JAN

1 stop6h 32mDelta

Deal found 12/10

$289

Wed 12/175:35 amMDW - JAN

2 stops6h 50mSouthwest

Deal found 12/10

$294

Tue 12/306:08 pmMDW - JAN

2 stops14h 52mDelta

Deal found 12/11

$342

Sun 12/145:13 pmMDW - JAN

1 stop5h 52mDelta

Deal found 12/11

$379

Sun 12/146:45 amMDW - JAN

2 stops7h 45mSouthwest

Deal found 12/11

$384

Sun 12/289:50 amMDW - JAN

1 stop7h 02mDelta

Deal found 12/11

$480

Find flight deals from Midway to Jackson

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$279 (Delta)
One-way from	$163 (Delta)
Popular in	January
Cheapest in	April
Average price	$421

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. 10% potential increase in price ($49 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

Search Deals

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Jackson that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sun 1/18

6:45 am-11:17 am

1 stop4h 32m

Jackson-Evers Intl

Sun 1/18

4:30 pm-10:07 pm

1 stop5h 37m

$279

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Tue 2/17

5:55 am-11:15 am

1 stop5h 20m

Jackson-Evers Intl

Thu 2/19

11:50 am-6:10 pm

1 stop6h 20m

$311

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Fri 1/16

6:45 am-11:17 am

1 stop4h 32m

Jackson-Evers Intl

Sun 1/18

4:30 pm-10:07 pm

1 stop5h 37m

$311

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Fri 2/6

5:55 am-11:15 am

1 stop5h 20m

Jackson-Evers Intl

Sun 2/8

6:40 am-1:30 pm

1 stop6h 50m

$367

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Wed 12/31

10:50 am-7:55 pm

2 stops9h 05m

Jackson-Evers Intl

Thu 1/8

6:40 am-4:30 pm

2 stops9h 50m

$383

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sun 3/8

2:10 pm-7:20 pm

1 stop5h 10m

Jackson-Evers Intl

Fri 3/13

5:30 am-3:20 pm

2 stops9h 50m

$392

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Fri 12/26

5:00 am-11:05 am

1 stop6h 05m

Jackson-Evers Intl

Wed 12/31

3:40 pm-9:05 pm

1 stop5h 25m

$396

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Fri 1/16

10:45 am-6:05 pm

1 stop7h 20m

Jackson-Evers Intl

Sun 1/18

1:25 pm-6:05 pm

1 stop4h 40m

$401

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Fri 1/2

5:00 am-11:05 am

1 stop6h 05m

Jackson-Evers Intl

Sun 1/4

6:05 pm-11:05 pm

1 stop5h 00m

$404

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Thu 1/8

6:45 am-11:17 am

1 stop4h 32m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 19 results

Compare providers for flights from Midway to Jackson

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Jackson in December.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Priceline	Price Accuracy1 star	Trust 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Jackson, Mississippi flight deals on Cheapflights vs. eDreams >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 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 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

What’s the top layover airport for flights from Chicago Midway Airport to Jackson, Mississippi?

Nashville (BNA) – chosen by Cheapflights users on 83% of 1-stop itineraries from Chicago Midway Airport to Jackson, Mississippi on Cheapflights.

What’s the cheapest layover airport for flights from Chicago Midway Airport to Jackson, Mississippi?

Houston (HOU) is the most affordable 1-stop option, with an average round-trip price of $366.

What’s the fastest layover option from Chicago Midway Airport to Jackson, Mississippi?

Flights via Nashville (BNA) have the shortest average one-way travel time for 1-stop routes: 4h 55m.

Which airport typically offers the quickest layover for flights from Chicago Midway Airport to Jackson, Mississippi?

Flights via Houston (HOU) offer the fastest connection on this route, with an average layover time of 1h 08m.

Reviews of airlines servicing Jackson

See what other customers who have flown with Southwest and Delta 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

7.9

Good

4,253 reviews

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

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

8,007 reviews

Southwest

7.9

Good

4,253 reviews

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

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 2 different airlines.
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 32m. The time it takes to get you to your destination can typically vary by up to 48m. Chicago Midway Airport and Jackson, Mississippi are separated by a distance of 667 mi. This flight may include one or multiple stops.
What are the cheapest airlines flying from Chicago Midway Airport to Jackson, Mississippi round-trip?
According to our current data, Delta ($149), and Southwest ($316) offers the cheapest pricing from Chicago Midway Airport to Jackson, Mississippi. Users have found that Delta is 65% 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

Vicksburg

Clinton

Flowood

Pearl

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Top 2 airlines flying from Midway to Jackson

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$248	Average$456	FlexibilityNo cancel fee	On-timeN/A
Southwest	Cheapest$316	Average$476	FlexibilityNo cancel fee	On-time63%

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$163+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midway to Jackson with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Midway to Jackson

Cheapest flights from Midway to JacksonExplore 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 December 12, 2025.

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 December 12, 2025.

Find flight deals from Midway to Jackson

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Jackson that are best for you.

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 December.

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Jackson

What’s the top layover airport for flights from Chicago Midway Airport to Jackson, Mississippi?

What’s the cheapest layover airport for flights from Chicago Midway Airport to Jackson, Mississippi?

What’s the fastest layover option from Chicago Midway Airport to Jackson, Mississippi?

Which airport typically offers the quickest layover for flights from Chicago Midway Airport to Jackson, Mississippi?

Reviews of airlines servicing Jackson

See what other customers who have flown with Southwest and Delta 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.

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?

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

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

Can I find deals for flights from Midway to Jackson that include hotel bookings?

How can I find direct flights from Midway to Jackson?

Can I find deals for business class flights from Midway to Jackson?

Traveling to a place near Jackson?

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Alternative routes for Midway to Jackson

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Top 2 airlines flying from Midway to Jackson

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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 December 12, 2025.