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Cheap flights from Jackson, Mississippi to Chicago from $128

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 12/31. 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
0 bags

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Find the cheapest flights from Jackson, Mississippi to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
12:11 pm - 4:29 pm
JAN
-
MDW
4h 18m1 stop
Delta Logo
11:21 am - 6:14 pm
MDW
-
JAN
6h 53m1 stop
$276Delta
Wed, Jan 14 - Sat, Jan 17
Delta Logo
10:57 am - 5:45 pm
JAN
-
MDW
6h 48m1 stop
Delta Logo
4:13 pm - 11:07 pm
MDW
-
JAN
6h 54m1 stop
$367Delta
Thu, Feb 12 - Sun, Feb 15
Southwest Logo
5:20 am - 2:30 pm
JAN
-
MDW
9h 10m2 stops
Southwest Logo
10:45 am - 6:05 pm
MDW
-
JAN
7h 20m1 stop
$372Southwest
Thu, Feb 12 - Sun, Feb 15
Southwest Logo
5:20 am - 2:30 pm
JAN
-
MDW
9h 10m2 stops
Southwest Logo
12:20 pm - 8:55 pm
MDW
-
JAN
8h 35m2 stops
$377Southwest
Thu, Feb 12 - Sun, Feb 15
Southwest Logo
6:00 am - 2:20 pm
JAN
-
MDW
8h 20m2 stops
Southwest Logo
8:00 am - 7:05 pm
MDW
-
JAN
11h 05m2 stops
$383Southwest
Sat, May 9 - Thu, May 14
Delta Logo
7:48 am - 2:44 pm
JAN
-
MDW
6h 56m1 stop
Delta Logo
6:00 am - 11:18 am
MDW
-
JAN
5h 18m1 stop
$387Delta
Thu, Jan 1 - Sun, Jan 4
Southwest Logo
6:20 pm - 11:05 pm
JAN
-
MDW
4h 45m1 stop
Southwest Logo
8:00 am - 7:05 pm
MDW
-
JAN
11h 05m2 stops
$425Southwest
Wed, May 20 - Mon, May 25
Southwest Logo
12:20 pm - 5:40 pm
JAN
-
MDW
5h 20m1 stop
Southwest Logo
6:30 am - 11:35 am
MDW
-
JAN
5h 05m1 stop
$427Southwest
Thu, Mar 12 - Sun, Mar 15
Southwest Logo
6:30 am - 2:55 pm
JAN
-
MDW
8h 25m2 stops
Southwest Logo
8:00 am - 7:05 pm
MDW
-
JAN
11h 05m2 stops
$430Southwest
Wed, May 20 - Mon, May 25
Southwest Logo
5:30 am - 3:20 pm
JAN
-
MDW
9h 50m2 stops
Southwest Logo
6:30 am - 11:35 am
MDW
-
JAN
5h 05m1 stop
$432Southwest
Thu, Mar 12 - Sun, Mar 15

Southwest flights from Jackson, Mississippi to Chicago Midway Airport

Our best Southwest deals on Jackson, Mississippi to Chicago Midway Airport flight tickets
Southwest
Dec 31
JAN3:40 pmJackson-Evers Intl
5h 25m
1 stop
MDW9:05 pmChicago Midway
Jan 1
MDW6:35 amChicago Midway
8h 30m
1 stop
JAN3:05 pmJackson-Evers Intl
$295
Find similar
Southwest
Feb 12
JAN5:20 amJackson-Evers Intl
9h 10m
2 stops
MDW2:30 pmChicago Midway
Feb 15
MDW10:45 amChicago Midway
7h 20m
1 stop
JAN6:05 pmJackson-Evers Intl
$372
Find similar
Southwest
Feb 12
JAN5:20 amJackson-Evers Intl
9h 10m
2 stops
MDW2:30 pmChicago Midway
Feb 15
MDW12:20 pmChicago Midway
8h 35m
2 stops
JAN8:55 pmJackson-Evers Intl
$377
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
Jan 16
JAN4:58 pmJackson-Evers Intl
5h 09m
1 stop
MDW10:07 pmChicago Midway
Jan 18
MDW6:45 amChicago Midway
4h 32m
1 stop
JAN11:17 amJackson-Evers Intl
$321
Find similar
Delta
Feb 12
JAN5:30 amJackson-Evers Intl
4h 24m
1 stop
MDW9:54 amChicago Midway
Feb 15
MDW4:13 pmChicago Midway
6h 54m
1 stop
JAN11:07 pmJackson-Evers Intl
$367
Find similar
Delta
Jan 1
JAN7:48 amJackson-Evers Intl
6h 56m
1 stop
MDW2:44 pmChicago Midway
Jan 4
MDW6:00 amChicago Midway
5h 18m
1 stop
JAN11:18 amJackson-Evers Intl
$387
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 December 22, 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

Wed 1/14

12:11 pm-4:29 pm

1 stop4h 18m

Chicago Midway

Sat 1/17

11:21 am-6:14 pm

1 stop6h 53m

$276

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 2/12

10:57 am-5:45 pm

1 stop6h 48m

Chicago Midway

Sun 2/15

4:13 pm-11:07 pm

1 stop6h 54m

$367

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 2/12

5:20 am-2:30 pm

2 stops9h 10m

Chicago Midway

Sun 2/15

10:45 am-6:05 pm

1 stop7h 20m

$372

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 2/12

5:20 am-2:30 pm

2 stops9h 10m

Chicago Midway

Sun 2/15

12:20 pm-8:55 pm

2 stops8h 35m

$377

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sat 5/9

6:00 am-2:20 pm

2 stops8h 20m

Chicago Midway

Thu 5/14

8:00 am-7:05 pm

2 stops11h 05m

$383

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 1/1

7:48 am-2:44 pm

1 stop6h 56m

Chicago Midway

Sun 1/4

6:00 am-11:18 am

1 stop5h 18m

$387

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 5/20

6:20 pm-11:05 pm

1 stop4h 45m

Chicago Midway

Mon 5/25

8:00 am-7:05 pm

2 stops11h 05m

$425

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 3/12

12:20 pm-5:40 pm

1 stop5h 20m

Chicago Midway

Sun 3/15

6:30 am-11:35 am

1 stop5h 05m

$427

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 5/20

6:30 am-2:55 pm

2 stops8h 25m

Chicago Midway

Mon 5/25

8:00 am-7:05 pm

2 stops11h 05m

$430

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 3/12

5:30 am-3:20 pm

2 stops9h 50m

Chicago Midway

Sun 3/15

6:30 am-11:35 am

1 stop5h 05m

$432

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 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

Fastest flight time

4h 21m

Direct flights

None
The fastest flight from Jackson, Mississippi to Chicago Midway Airport takes 4h 21m
There are no direct flights from Jackson, Mississippi to Chicago Midway Airport. There are no popular flight routes from Jackson, Mississippi to 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. 4h 21m 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
7.9
8,014 reviews
Search Delta flights
SouthwestPriceFrom $234Free CancellationRating
8.0
4,253 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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