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Cheap flights from Jackson, Mississippi to Chicago from $158

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Jackson, Mississippi to Chicago departing on 9/25. 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 Jackson, Mississippi to Chicago

Cheap round-trip flights

Delta Logo
5:58 pm - 10:14 pmJAN-MDW
4h 16m1 stop
Delta Logo
6:00 am - 10:01 amMDW-JAN
4h 01m1 stop
$237Delta
Find Deal
Tue, Oct 21 - Wed, Oct 22
Delta Logo
3:01 pm - 9:44 pmJAN-MDW
6h 43m1 stop
Delta Logo
4:25 pm - 11:20 pmMDW-JAN
6h 55m1 stop
$259Delta
Find Deal
Sun, Aug 24 - Wed, Aug 27
Southwest Logo
2:10 pm - 7:50 pmJAN-MDW
5h 40m1 stop
Southwest Logo
7:55 am - 1:30 pmMDW-JAN
5h 35m1 stop
$298Southwest
Find Deal
Fri, Aug 22 - Mon, Aug 25
Delta Logo
5:50 am - 11:48 amJAN-MDW
5h 58m1 stop
Delta Logo
6:04 am - 10:46 amMDW-JAN
4h 42m1 stop
$302Delta
Find Deal
Wed, Aug 20 - Sun, Aug 24
Southwest Logo
2:10 pm - 7:50 pmJAN-MDW
5h 40m1 stop
Southwest Logo
6:30 am - 1:30 pmMDW-JAN
7h 00m2 stops
$303Southwest
Find Deal
Fri, Aug 22 - Mon, Aug 25
Delta Logo
3:01 pm - 9:44 pmJAN-MDW
6h 43m1 stop
Delta Logo
4:25 pm - 11:20 pmMDW-JAN
6h 55m1 stop
$308Delta
Find Deal
Wed, Aug 20 - Mon, Aug 25
Southwest Logo
6:30 am - 2:45 pmJAN-MDW
8h 15m2 stops
Southwest Logo
12:30 pm - 6:25 pmMDW-JAN
5h 55m1 stop
$312Southwest
Find Deal
Tue, Oct 21 - Wed, Oct 22
Delta Logo
3:10 pm - 9:36 pmJAN-MDW
6h 26m1 stop
Delta Logo
6:30 pm - 11:17 pmMDW-JAN
4h 47m1 stop
$315Delta
Find Deal
Fri, Sep 26 - Mon, Sep 29
Southwest Logo
6:30 am - 2:05 pmJAN-MDW
7h 35m2 stops
Southwest Logo
5:50 am - 12:30 pmMDW-JAN
6h 40m2 stops
$317Southwest
Find Deal
Tue, Oct 21 - Wed, Oct 22
Delta Logo
3:10 pm - 9:36 pmJAN-MDW
6h 26m1 stop
Delta Logo
6:00 am - 10:45 amMDW-JAN
4h 45m1 stop
$327Delta
Find Deal
Thu, Sep 25 - Sun, Sep 28

Southwest flights from Jackson, Mississippi to Chicago Midway Airport

Our best Southwest deals on Jackson, Mississippi to Chicago Midway Airport flight tickets
Southwest
Aug 22
JAN2:10 pmJackson-Evers Intl
5h 40m
1 stop
MDW7:50 pmChicago Midway
Aug 25
MDW7:55 amChicago Midway
5h 35m
1 stop
JAN1:30 pmJackson-Evers Intl
$298
Find similar
Southwest
Aug 22
JAN2:10 pmJackson-Evers Intl
5h 40m
1 stop
MDW7:50 pmChicago Midway
Aug 25
MDW6:30 amChicago Midway
7h 00m
2 stops
JAN1:30 pmJackson-Evers Intl
$303
Find similar
Southwest
Oct 21
JAN6:30 amJackson-Evers Intl
8h 15m
2 stops
MDW2:45 pmChicago Midway
Oct 22
MDW12:30 pmChicago Midway
5h 55m
1 stop
JAN6:25 pmJackson-Evers Intl
$312
Find similar

Delta flights from Jackson, Mississippi to Chicago Midway Airport

Our best Delta deals on Jackson, Mississippi to Chicago Midway Airport flight tickets
Delta
Oct 21
JAN5:58 pmJackson-Evers Intl
4h 16m
1 stop
MDW10:14 pmChicago Midway
Oct 22
MDW6:00 amChicago Midway
4h 01m
1 stop
JAN10:01 amJackson-Evers Intl
$237
Find similar
Delta
Aug 24
JAN3:01 pmJackson-Evers Intl
6h 43m
1 stop
MDW9:44 pmChicago Midway
Aug 27
MDW4:25 pmChicago Midway
6h 55m
1 stop
JAN11:20 pmJackson-Evers Intl
$259
Find similar
Delta
Aug 20
JAN5:50 amJackson-Evers Intl
5h 58m
1 stop
MDW11:48 amChicago Midway
Aug 24
MDW6:04 amChicago Midway
4h 42m
1 stop
JAN10:46 amJackson-Evers Intl
$302
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Jackson, Mississippi to Chicago Midway Airport 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 1, 2025.
Use the filters below to find and compare flights from Jackson, Mississippi to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 10/21

5:58 pm-10:14 pm

1 stop4h 16m

Chicago Midway

Wed 10/22

6:00 am-10:01 am

1 stop4h 01m

$237

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sun 8/24

3:01 pm-9:44 pm

1 stop6h 43m

Chicago Midway

Wed 8/27

4:25 pm-11:20 pm

1 stop6h 55m

$259

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 8/22

2:10 pm-7:50 pm

1 stop5h 40m

Chicago Midway

Mon 8/25

7:55 am-1:30 pm

1 stop5h 35m

$298

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 8/20

5:50 am-11:48 am

1 stop5h 58m

Chicago Midway

Sun 8/24

6:04 am-10:46 am

1 stop4h 42m

$302

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 8/22

2:10 pm-7:50 pm

1 stop5h 40m

Chicago Midway

Mon 8/25

6:30 am-1:30 pm

2 stops7h 00m

$303

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 8/20

3:01 pm-9:44 pm

1 stop6h 43m

Chicago Midway

Mon 8/25

4:25 pm-11:20 pm

1 stop6h 55m

$308

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 10/21

6:30 am-2:45 pm

2 stops8h 15m

Chicago Midway

Wed 10/22

12:30 pm-6:25 pm

1 stop5h 55m

$312

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 9/26

3:10 pm-9:36 pm

1 stop6h 26m

Chicago Midway

Mon 9/29

6:30 pm-11:17 pm

1 stop4h 47m

$315

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 10/21

6:30 am-2:05 pm

2 stops7h 35m

Chicago Midway

Wed 10/22

5:50 am-12:30 pm

2 stops6h 40m

$317

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 9/25

3:10 pm-9:36 pm

1 stop6h 26m

Chicago Midway

Sun 9/28

6:00 am-10:45 am

1 stop4h 45m

$327

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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 day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Jackson, Mississippi. The lowest ticket price found for a Wednesday departure recently was $261. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Jackson, Mississippi because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $582.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Jackson, Mississippi in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $382 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $491. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

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

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

Best Price Found

$158

Fastest flight time

3h 35m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Jackson, Mississippi in the past 72 hours is $158. The best round-trip flight deal from Jackson, Mississippi to Chicago Midway Airport found on momondo in the last 72 hours is $237.
The fastest flight from Jackson, Mississippi to Chicago Midway Airport takes 3h 35m
There are no direct flights from Jackson, Mississippi to Chicago Midway Airport. Popular non-direct route for this connection is Jackson-Evers Intl Airport - Chicago Midway Airport.
Search flight deals

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

    There are 668.7 mi between Jackson-Evers Intl and Chicago Midway. 3h 35m is a normal flight duration for this route.

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

    Prices for flights from Jackson-Evers Intl Airport to Chicago Midway Airport are refreshed on a daily basis.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Jackson-Evers Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from Jackson, Mississippi to Chicago Midway Airport

Compare and see reviews for airlines that fly from Jackson, Mississippi to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $196Free CancellationRating
8.0
7,981 reviews
Search Delta flights
SouthwestPriceFrom $234Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

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Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Jackson.

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

Yes. momondo allows you to filter the results for Jackson to Chicago flights to just show those with flexible booking policies.

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

Once you have performed a search for Jackson to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Of course. momondo tracks the price of Jackson to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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