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Cheap flights from Chicago Midway Airport to Jackson from $129

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Jackson departing on 10/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to Jackson (MDW-JAN)

Cheap round-trip flights

Southwest Logo
12:15 pm - 7:55 pmMDW-JAN
7h 40m1 stop
Southwest Logo
1:10 pm - 7:40 pmJAN-MDW
6h 30m1 stop
$267Southwest
Find Deal
Sat, Oct 4 - Tue, Oct 7
Southwest Logo
7:00 am - 12:10 pmMDW-JAN
5h 10m1 stop
Southwest Logo
6:30 am - 2:50 pmJAN-MDW
8h 20m2 stops
$272Southwest
Find Deal
Sat, Oct 4 - Tue, Oct 7
Delta Logo
6:00 am - 11:18 amMDW-JAN
5h 18m1 stop
Delta Logo
7:16 pm - 11:32 pmJAN-MDW
4h 16m1 stop
$287Delta
Find Deal
Sat, Nov 8 - Mon, Nov 10
Delta Logo
6:00 am - 11:18 amMDW-JAN
5h 18m1 stop
Delta Logo
7:16 pm - 11:32 pmJAN-MDW
4h 16m1 stop
$298Delta
Find Deal
Sat, Nov 8 - Mon, Nov 10
Southwest Logo
7:55 am - 1:30 pmMDW-JAN
5h 35m1 stop
Southwest Logo
8:05 pm - 12:45 amJAN-MDW
4h 40m1 stop
$307Southwest
Find Deal
Mon, Sep 29 - Mon, Oct 6
Southwest Logo
11:45 am - 6:10 pmMDW-JAN
6h 25m1 stop
Southwest Logo
6:35 pm - 12:05 amJAN-MDW
5h 30m1 stop
$308Southwest
Find Deal
Wed, Sep 17 - Fri, Sep 19
Southwest Logo
8:20 am - 2:45 pmMDW-JAN
6h 25m2 stops
Southwest Logo
6:30 am - 2:50 pmJAN-MDW
8h 20m2 stops
$312Southwest
Find Deal
Sat, Oct 4 - Tue, Oct 7
Southwest Logo
5:45 am - 11:20 amMDW-JAN
5h 35m1 stop
Southwest Logo
7:35 pm - 12:25 amJAN-MDW
4h 50m1 stop
$347Southwest
Find Deal
Fri, Sep 26 - Sun, Sep 28
Southwest Logo
7:45 am - 1:30 pmMDW-JAN
5h 45m2 stops
Southwest Logo
8:05 pm - 12:45 amJAN-MDW
4h 40m1 stop
$352Southwest
Find Deal
Mon, Sep 29 - Mon, Oct 6
Southwest Logo
11:45 am - 6:10 pmMDW-JAN
6h 25m1 stop
Southwest Logo
5:40 am - 1:45 pmJAN-MDW
8h 05m2 stops
$358Southwest
Find Deal
Wed, Sep 17 - Fri, Sep 19

Delta flights from Chicago Midway Airport to Jackson, Mississippi

Our best Delta deals on Chicago Midway Airport to Jackson, Mississippi flight tickets
Delta
Nov 8
MDW6:00 amChicago Midway
5h 18m
1 stop
JAN11:18 amJackson-Evers Intl
Nov 10
JAN7:16 pmJackson-Evers Intl
4h 16m
1 stop
MDW11:32 pmChicago Midway
$287
Find similar
Delta
Nov 8
MDW6:00 amChicago Midway
5h 18m
1 stop
JAN11:18 amJackson-Evers Intl
Nov 10
JAN7:16 pmJackson-Evers Intl
4h 16m
1 stop
MDW11:32 pmChicago Midway
$298
Find similar
Delta
Sep 4
MDW4:25 pmChicago Midway
4h 12m
1 stop
JAN8:37 pmJackson-Evers Intl
Sep 13
JAN3:10 pmJackson-Evers Intl
6h 00m
1 stop
MDW9:10 pmChicago Midway
$347
Find similar

Southwest flights from Chicago Midway Airport to Jackson, Mississippi

Our best Southwest deals on Chicago Midway Airport to Jackson, Mississippi flight tickets
Southwest
Oct 4
MDW12:15 pmChicago Midway
7h 40m
1 stop
JAN7:55 pmJackson-Evers Intl
Oct 7
JAN1:10 pmJackson-Evers Intl
6h 30m
1 stop
MDW7:40 pmChicago Midway
$267
Find similar
Southwest
Oct 4
MDW7:00 amChicago Midway
5h 10m
1 stop
JAN12:10 pmJackson-Evers Intl
Oct 7
JAN6:30 amJackson-Evers Intl
8h 20m
2 stops
MDW2:50 pmChicago Midway
$272
Find similar
Southwest
Sep 29
MDW7:55 amChicago Midway
5h 35m
1 stop
JAN1:30 pmJackson-Evers Intl
Oct 6
JAN8:05 pmJackson-Evers Intl
4h 40m
1 stop
MDW12:45 amChicago Midway
$307
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Jackson, Mississippi 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, momondo users made 832,500 searches. Data last updated August 28, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Jackson, Mississippi that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 10/4

12:15 pm-7:55 pm

1 stop7h 40m

Jackson-Evers Intl

Tue 10/7

1:10 pm-7:40 pm

1 stop6h 30m

$267

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 10/4

7:00 am-12:10 pm

1 stop5h 10m

Jackson-Evers Intl

Tue 10/7

6:30 am-2:50 pm

2 stops8h 20m

$272

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 11/8

6:00 am-11:18 am

1 stop5h 18m

Jackson-Evers Intl

Mon 11/10

7:16 pm-11:32 pm

1 stop4h 16m

$287

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 11/8

6:00 am-11:18 am

1 stop5h 18m

Jackson-Evers Intl

Mon 11/10

7:16 pm-11:32 pm

1 stop4h 16m

$298

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Mon 9/29

7:55 am-1:30 pm

1 stop5h 35m

Jackson-Evers Intl

Mon 10/6

8:05 pm-12:45 am

1 stop4h 40m

$307

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Wed 9/17

11:45 am-6:10 pm

1 stop6h 25m

Jackson-Evers Intl

Fri 9/19

6:35 pm-12:05 am

1 stop5h 30m

$308

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 10/4

8:20 am-2:45 pm

2 stops6h 25m

Jackson-Evers Intl

Tue 10/7

6:30 am-2:50 pm

2 stops8h 20m

$312

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Fri 9/26

5:45 am-11:20 am

1 stop5h 35m

Jackson-Evers Intl

Sun 9/28

7:35 pm-12:25 am

1 stop4h 50m

$347

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Mon 9/29

7:45 am-1:30 pm

2 stops5h 45m

Jackson-Evers Intl

Mon 10/6

8:05 pm-12:45 am

1 stop4h 40m

$352

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Wed 9/17

11:45 am-6:10 pm

1 stop6h 25m

Jackson-Evers Intl

Fri 9/19

5:40 am-1:45 pm

2 stops8h 05m

$358

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first
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See travel insights to Jackson from

How to get the cheapest flight ticket from Chicago Midway Airport to Jackson, Mississippi

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Jackson, Mississippi?

The cheapest month to fly to Jackson, Mississippi from Chicago Midway Airport is in April. Flight prices, which tend to average around $248, are often lower during this time because this is during the off-season. If you’re not able to fly to Jackson, Mississippi in April, then May is your next best option. Flight prices from Chicago Midway Airport to Jackson, Mississippi during May average around $316.

What is the cheapest day to depart on your flight to Jackson, Mississippi?

The cheapest day to depart from Chicago Midway Airport to Jackson, Mississippi is on a Wednesday when prices can be found for as low as $320. On the other hand, Sunday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $496.

What is the cheapest time of day to depart on your flight to Jackson, Mississippi?

Our most recent data shows that the best time of day to fly to Jackson, Mississippi is in the afternoon. Flights from Chicago Midway Airport to Jackson, Mississippi during this time can be as low as $386. In contrast, the most expensive time of day to depart to Jackson, Mississippi is at noon when prices are around $436.

When to book flights from Chicago Midway Airport to Jackson, Mississippi

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Jackson, Mississippi according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Jackson, Mississippi (MDW to JAN) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Jackson, Mississippi

Direct flights

None
There are no direct flights from Chicago Midway Airport to Jackson, Mississippi. There are no popular flight routes from Chicago Midway Airport to Jackson, Mississippi.
Search flight deals

  • How far is Chicago Midway to Jackson-Evers Intl by plane?

    The straight-line distance from Chicago Midway to Jackson-Evers Intl is 668.7 mi. 4h 01m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago Midway Airport to Jackson-Evers Intl Airport?

    Prices for flights from Chicago Midway Airport to Jackson-Evers Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Jackson-Evers Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Jackson-Evers Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Jackson-Evers Intl Airport.

  • What documentation or ID do you need to fly to Jackson-Evers Intl Airport?

    The necessary travel and health documents for your Jackson-Evers Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to Jackson, Mississippi?

Best airlines flying from Chicago Midway Airport to Jackson, Mississippi

Compare and see reviews for airlines that fly from Chicago Midway Airport to Jackson, Mississippi with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $248Free CancellationRating
7.9
7,977 reviews
Search Delta flights
SouthwestPriceFrom $316Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

Traveling to a place near Jackson?

Book flights to Jackson if you plan to visit one of these locations
Vicksburg
Flowood
Clinton
Pearl
Brandon
Richland

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Jackson?

Finding the right flight to Jackson from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Jackson quick and easy, saving you time and money.

Can I find flights from Chicago to Jackson with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Jackson from Chicago with this policy.

How can momondo help me find flights from Chicago to Jackson?

momondo helps you find the best flight between Chicago and Jackson by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Jackson right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Jackson flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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