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Cheap flights from Chicago Midway Airport to Jackson from $155

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 9/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to Jackson

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
2:40 pm - 6:05 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
3h 25m1 stop Nashville Intl
Southwest Logo
6:40 pm - 11:15 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
4h 35m1 stop Houston Hobby
$309Southwest
Wed, Sep 2 - Tue, Sep 8
Southwest Logo
10:10 am - 6:05 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
7h 55m2 stops Lambert-St Louis Nashville Intl
Southwest Logo
6:40 pm - 11:15 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
4h 35m1 stop Houston Hobby
$314Southwest
Wed, Sep 2 - Tue, Sep 8
Southwest Logo
1:00 pm - 6:05 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
5h 05m2 stops Louisville Intl Nashville Intl
Southwest Logo
12:55 pm - 9:20 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
8h 25m2 stops Nashville Intl Baltimore/Washington
$319Southwest
Tue, Sep 29 - Tue, Oct 6
Delta Logo
6:05 am - 11:46 amMDW  Chicago Midway-JAN Jackson-Evers Intl
5h 41m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:14 pm - 10:44 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
5h 30m1 stop Atlanta Hartsfield-Jackson
$322Delta
Fri, Sep 11 - Tue, Sep 15
Southwest Logo
5:25 am - 12:00 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
6h 35m1 stop Houston Hobby
Southwest Logo
7:05 am - 3:20 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
8h 15m2 stops Houston Hobby Dallas Love Field
$327Southwest
Fri, Sep 11 - Tue, Sep 15
Southwest Logo
11:05 am - 7:50 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
8h 45m2 stops Lambert-St Louis Nashville Intl
Southwest Logo
12:55 pm - 9:20 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
8h 25m2 stops Nashville Intl Baltimore/Washington
$328Southwest
Mon, Oct 5 - Tue, Oct 6
Southwest Logo
5:20 pm - 10:05 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
4h 45m1 stop Houston Hobby
Southwest Logo
8:15 pm - 1:05 amJAN  Jackson-Evers Intl-MDW Chicago Midway
4h 50m1 stop Houston Hobby
$331Southwest
Fri, Nov 6 - Mon, Nov 9
Southwest Logo
11:05 am - 7:50 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
8h 45m2 stops Lambert-St Louis Nashville Intl
Southwest Logo
12:30 pm - 8:35 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
8h 05m2 stops Houston Hobby Dallas Love Field
$332Southwest
Fri, Oct 2 - Sat, Oct 3
Southwest Logo
11:10 am - 10:05 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
10h 55m2 stops Lambert-St Louis Houston Hobby
Southwest Logo
5:30 am - 2:40 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
9h 10m2 stops Houston Hobby Austin Bergstrom
$338Southwest
Thu, Dec 17 - Wed, Dec 23
Southwest Logo
11:05 am - 7:50 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
8h 45m2 stops Lambert-St Louis Nashville Intl
Southwest Logo
5:55 am - 3:05 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
9h 10m2 stops Houston Hobby Lambert-St Louis
$341Southwest
Fri, Oct 23 - Mon, Oct 26

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Southwest flights from Chicago Midway Airport to Jackson, Mississippi

Our best Southwest deals on Chicago Midway Airport to Jackson, Mississippi flight tickets
Southwest
Sep 2
MDW2:40 pmChicago Midway
3h 25m
1 stop
JAN6:05 pmJackson-Evers Intl
Sep 8
JAN6:40 pmJackson-Evers Intl
4h 35m
1 stop
MDW11:15 pmChicago Midway
$309
Southwest
Sep 2
MDW10:10 amChicago Midway
7h 55m
2 stops
JAN6:05 pmJackson-Evers Intl
Sep 8
JAN6:40 pmJackson-Evers Intl
4h 35m
1 stop
MDW11:15 pmChicago Midway
$314
Southwest
Sep 29
MDW1:00 pmChicago Midway
5h 05m
2 stops
JAN6:05 pmJackson-Evers Intl
Oct 6
JAN12:55 pmJackson-Evers Intl
8h 25m
2 stops
MDW9:20 pmChicago Midway
$319

Delta flights from Chicago Midway Airport to Jackson, Mississippi

Our best Delta deals on Chicago Midway Airport to Jackson, Mississippi flight tickets
Delta
Sep 11
MDW6:05 amChicago Midway
5h 41m
1 stop
JAN11:46 amJackson-Evers Intl
Sep 15
JAN5:14 pmJackson-Evers Intl
5h 30m
1 stop
MDW10:44 pmChicago Midway
$322
Delta
Dec 11
MDW6:00 amChicago Midway
4h 29m
1 stop
JAN10:29 amJackson-Evers Intl
Dec 13
JAN5:30 amJackson-Evers Intl
6h 35m
1 stop
MDW12:05 pmChicago Midway
$363
Delta
Sep 25
MDW5:10 pmChicago Midway
6h 11m
1 stop
JAN11:21 pmJackson-Evers Intl
Sep 27
JAN7:51 amJackson-Evers Intl
4h 03m
1 stop
MDW11:54 amChicago Midway
$372

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 18, 2026.
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

Cheapest round-trip
Quickest round-trip

ChicagoJackson

MDW Chicago Midway - JAN Jackson-Evers Intl

MDWJAN

Chicago Midway

Wed 9/2

2:40 pm-6:05 pm

1 stop3h 25m

Jackson-Evers Intl

Tue 9/8

6:40 pm-11:15 pm

1 stop4h 35m

$309

ChicagoJackson

MDW Chicago Midway - JAN Jackson-Evers Intl

MDWJAN

Chicago Midway

Wed 9/2

10:10 am-6:05 pm

2 stops7h 55m

Jackson-Evers Intl

Tue 9/8

6:40 pm-11:15 pm

1 stop4h 35m

$314

ChicagoJackson

MDW Chicago Midway - JAN Jackson-Evers Intl

MDWJAN

Chicago Midway

Tue 9/29

1:00 pm-6:05 pm

2 stops5h 05m

Jackson-Evers Intl

Tue 10/6

12:55 pm-9:20 pm

2 stops8h 25m

$319

ChicagoJackson

MDW Chicago Midway - JAN Jackson-Evers Intl

MDWJAN

Chicago Midway

Fri 9/11

6:05 am-11:46 am

1 stop5h 41m

Jackson-Evers Intl

Tue 9/15

5:14 pm-10:44 pm

1 stop5h 30m

$322

ChicagoJackson

MDW Chicago Midway - JAN Jackson-Evers Intl

MDWJAN

Chicago Midway

Fri 9/11

5:25 am-12:00 pm

1 stop6h 35m

Jackson-Evers Intl

Tue 9/15

7:05 am-3:20 pm

2 stops8h 15m

$327

ChicagoJackson

MDW Chicago Midway - JAN Jackson-Evers Intl

MDWJAN

Chicago Midway

Mon 10/5

11:05 am-7:50 pm

2 stops8h 45m

Jackson-Evers Intl

Tue 10/6

12:55 pm-9:20 pm

2 stops8h 25m

$328

ChicagoJackson

MDW Chicago Midway - JAN Jackson-Evers Intl

MDWJAN

Chicago Midway

Fri 11/6

5:20 pm-10:05 pm

1 stop4h 45m

Jackson-Evers Intl

Mon 11/9

8:15 pm-1:05 am

1 stop4h 50m

$331

ChicagoJackson

MDW Chicago Midway - JAN Jackson-Evers Intl

MDWJAN

Chicago Midway

Fri 10/2

11:05 am-7:50 pm

2 stops8h 45m

Jackson-Evers Intl

Sat 10/3

12:30 pm-8:35 pm

2 stops8h 05m

$332

ChicagoJackson

MDW Chicago Midway - JAN Jackson-Evers Intl

MDWJAN

Chicago Midway

Thu 12/17

11:10 am-10:05 pm

2 stops10h 55m

Jackson-Evers Intl

Wed 12/23

5:30 am-2:40 pm

2 stops9h 10m

$338

ChicagoJackson

MDW Chicago Midway - JAN Jackson-Evers Intl

MDWJAN

Chicago Midway

Fri 10/23

11:05 am-7:50 pm

2 stops8h 45m

Jackson-Evers Intl

Mon 10/26

5:55 am-3:05 pm

2 stops9h 10m

$341

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 airline that flies from Chicago Midway to Jackson-Evers Intl?

Southwest is the most popular carrier operating from Chicago Midway to Jackson-Evers Intl

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

Best Price Found

$155

Fastest flight time

3h 20m

Direct flights

None
The best one-way flight to Jackson, Mississippi from Chicago Midway Airport in the past 72 hours is $155. The best round-trip flight deal from Chicago Midway Airport to Jackson, Mississippi found on momondo in the last 72 hours is $309.
The fastest flight from Chicago Midway Airport to Jackson, Mississippi takes 3h 20m
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

Frequently asked questions about flying from Chicago Midway Airport to Jackson, Mississippi

  • 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. 3h 20m 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 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.

Traveling to a place near Jackson?

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

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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