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Cheap flights from Jackson, Mississippi to Chicago from $149

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 12/6. 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

Enter your travel dates to find the best prices.
Delta Logo
5:48 am - 9:54 amJAN-MDW
4h 06m1 stop
Delta Logo
12:50 pm - 7:30 pmMDW-JAN
6h 40m1 stop
$297Delta
Find Deal
Tue, Dec 2 - Tue, Dec 9
Southwest Logo
3:40 pm - 9:05 pmJAN-MDW
5h 25m1 stop
Southwest Logo
6:40 am - 3:05 pmMDW-JAN
8h 25m2 stops
$337Southwest
Find Deal
Tue, Dec 2 - Tue, Dec 9
Delta Logo
7:16 pm - 11:40 pmJAN-MDW
4h 24m1 stop
Delta Logo
6:00 am - 11:30 amMDW-JAN
5h 30m1 stop
$347Delta
Find Deal
Mon, Dec 1 - Mon, Dec 8
Delta Logo
9:16 am - 4:20 pmJAN-MDW
7h 04m1 stop
Delta Logo
6:00 am - 11:18 amMDW-JAN
5h 18m1 stop
$367Delta
Find Deal
Mon, Dec 22 - Fri, Dec 26
Southwest Logo
3:40 pm - 9:05 pmJAN-MDW
5h 25m1 stop
Southwest Logo
7:45 am - 4:35 pmMDW-JAN
8h 50m1 stop
$377Southwest
Find Deal
Wed, Dec 24 - Sat, Dec 27
Southwest Logo
1:10 pm - 8:45 pmJAN-MDW
7h 35m2 stops
Southwest Logo
6:40 am - 3:05 pmMDW-JAN
8h 25m2 stops
$382Southwest
Find Deal
Tue, Dec 2 - Tue, Dec 9
Southwest Logo
1:10 pm - 9:05 pmJAN-MDW
7h 55m2 stops
Southwest Logo
7:45 am - 4:35 pmMDW-JAN
8h 50m1 stop
$383Southwest
Find Deal
Wed, Dec 24 - Sat, Dec 27
Southwest Logo
3:40 pm - 9:05 pmJAN-MDW
5h 25m1 stop
Southwest Logo
9:50 am - 5:55 pmMDW-JAN
8h 05m2 stops
$397Southwest
Find Deal
Thu, Dec 25 - Sat, Dec 27
Southwest Logo
5:20 am - 2:05 pmJAN-MDW
8h 45m2 stops
Southwest Logo
5:00 am - 11:05 amMDW-JAN
6h 05m1 stop
$412Southwest
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Mon, Dec 22 - Fri, Dec 26
Southwest Logo
6:25 am - 2:10 pmJAN-MDW
7h 45m2 stops
Southwest Logo
9:50 am - 5:55 pmMDW-JAN
8h 05m2 stops
$417Southwest
Find Deal
Thu, Dec 25 - Sat, Dec 27

Delta flights from Jackson, Mississippi to Chicago Midway Airport

Our best Delta deals on Jackson, Mississippi to Chicago Midway Airport flight tickets
Delta
Dec 2
JAN5:48 amJackson-Evers Intl
4h 06m
1 stop
MDW9:54 amChicago Midway
Dec 9
MDW12:50 pmChicago Midway
6h 40m
1 stop
JAN7:30 pmJackson-Evers Intl
$297
Find similar
Delta
Dec 1
JAN7:16 pmJackson-Evers Intl
4h 24m
1 stop
MDW11:40 pmChicago Midway
Dec 8
MDW6:00 amChicago Midway
5h 30m
1 stop
JAN11:30 amJackson-Evers Intl
$347
Find similar
Delta
Dec 22
JAN9:16 amJackson-Evers Intl
7h 04m
1 stop
MDW4:20 pmChicago Midway
Dec 26
MDW6:00 amChicago Midway
5h 18m
1 stop
JAN11:18 amJackson-Evers Intl
$367
Find similar

Southwest flights from Jackson, Mississippi to Chicago Midway Airport

Our best Southwest deals on Jackson, Mississippi to Chicago Midway Airport flight tickets
Southwest
Dec 2
JAN3:40 pmJackson-Evers Intl
5h 25m
1 stop
MDW9:05 pmChicago Midway
Dec 9
MDW6:40 amChicago Midway
8h 25m
2 stops
JAN3:05 pmJackson-Evers Intl
$337
Find similar
Southwest
Dec 24
JAN3:40 pmJackson-Evers Intl
5h 25m
1 stop
MDW9:05 pmChicago Midway
Dec 27
MDW7:45 amChicago Midway
8h 50m
1 stop
JAN4:35 pmJackson-Evers Intl
$377
Find similar
Southwest
Dec 2
JAN1:10 pmJackson-Evers Intl
7h 35m
2 stops
MDW8:45 pmChicago Midway
Dec 9
MDW6:40 amChicago Midway
8h 25m
2 stops
JAN3:05 pmJackson-Evers Intl
$382
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 November 3, 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 12/2

5:48 am-9:54 am

1 stop4h 06m

Chicago Midway

Tue 12/9

12:50 pm-7:30 pm

1 stop6h 40m

$297

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 12/2

3:40 pm-9:05 pm

1 stop5h 25m

Chicago Midway

Tue 12/9

6:40 am-3:05 pm

2 stops8h 25m

$337

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Mon 12/1

7:16 pm-11:40 pm

1 stop4h 24m

Chicago Midway

Mon 12/8

6:00 am-11:30 am

1 stop5h 30m

$347

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Mon 12/22

9:16 am-4:20 pm

1 stop7h 04m

Chicago Midway

Fri 12/26

6:00 am-11:18 am

1 stop5h 18m

$367

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 12/24

3:40 pm-9:05 pm

1 stop5h 25m

Chicago Midway

Sat 12/27

7:45 am-4:35 pm

1 stop8h 50m

$377

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 12/2

1:10 pm-8:45 pm

2 stops7h 35m

Chicago Midway

Tue 12/9

6:40 am-3:05 pm

2 stops8h 25m

$382

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 12/24

1:10 pm-9:05 pm

2 stops7h 55m

Chicago Midway

Sat 12/27

7:45 am-4:35 pm

1 stop8h 50m

$383

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 12/25

3:40 pm-9:05 pm

1 stop5h 25m

Chicago Midway

Sat 12/27

9:50 am-5:55 pm

2 stops8h 05m

$397

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Mon 12/22

5:20 am-2:05 pm

2 stops8h 45m

Chicago Midway

Fri 12/26

5:00 am-11:05 am

1 stop6h 05m

$412

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 12/25

6:25 am-2:10 pm

2 stops7h 45m

Chicago Midway

Sat 12/27

9:50 am-5:55 pm

2 stops8h 05m

$417

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

Direct flights

None
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. 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
7.9
8,001 reviews
Search Delta flights
SouthwestPriceFrom $234Free CancellationRating
8.0
4,240 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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