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Cheap flights from Jackson, Mississippi to Chicago from $184

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 7/7. 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

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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
5:04 pm - 10:15 pm
JAN
-
MDW
5h 11m
1 stop
Delta Logo
6:00 am - 10:00 am
MDW
-
JAN
4h 00m
1 stop
$339Delta
Wed, Jul 8 - Tue, Jul 14
Southwest Logo
6:00 am - 12:15 pm
JAN
-
MDW
6h 15m
1 stop
Southwest Logo
5:05 am - 11:45 am
MDW
-
JAN
6h 40m
1 stop
$358Southwest
Sat, Jul 4 - Sat, Jul 11
Delta Logo
3:30 pm - 10:36 pm
JAN
-
MDW
7h 06m
1 stop
Delta Logo
5:10 pm - 11:11 pm
MDW
-
JAN
6h 01m
1 stop
$359Delta
Thu, Aug 13 - Tue, Aug 18
Southwest Logo
6:00 am - 2:25 pm
JAN
-
MDW
8h 25m
2 stops
Southwest Logo
5:05 am - 11:45 am
MDW
-
JAN
6h 40m
1 stop
$363Southwest
Sat, Jul 4 - Sat, Jul 11
Southwest Logo
12:40 pm - 7:30 pm
JAN
-
MDW
6h 50m
2 stops
Southwest Logo
7:50 am - 12:50 pm
MDW
-
JAN
5h 00m
1 stop
$364Southwest
Thu, Aug 13 - Tue, Aug 18
Southwest Logo
7:15 pm - 11:55 pm
JAN
-
MDW
4h 40m
1 stop
Southwest Logo
1:00 pm - 10:00 pm
MDW
-
JAN
9h 00m
2 stops
$368Southwest
Wed, Jul 8 - Thu, Jul 9
Southwest Logo
12:40 pm - 7:30 pm
JAN
-
MDW
6h 50m
2 stops
Southwest Logo
6:00 am - 12:50 pm
MDW
-
JAN
6h 50m
2 stops
$369Southwest
Thu, Aug 13 - Tue, Aug 18
Delta Logo
3:06 pm - 10:15 pm
JAN
-
MDW
7h 09m
1 stop
Delta Logo
5:10 pm - 11:09 pm
MDW
-
JAN
5h 59m
1 stop
$373Delta
Wed, Jul 8 - Fri, Jul 10
Southwest Logo
12:20 pm - 5:05 pm
JAN
-
MDW
4h 45m
1 stop
Southwest Logo
12:00 pm - 8:45 pm
MDW
-
JAN
8h 45m
1 stop
$374Southwest
Wed, Jul 1 - Tue, Jul 7
Southwest Logo
6:00 am - 1:00 pm
JAN
-
MDW
7h 00m
1 stop
Southwest Logo
5:55 am - 12:00 pm
MDW
-
JAN
6h 05m
1 stop
$377Southwest
Sat, Aug 22 - Mon, Aug 24

Southwest flights from Jackson, Mississippi to Chicago Midway Airport

Our best Southwest deals on Jackson, Mississippi to Chicago Midway Airport flight tickets
Southwest
Sep 5
JAN2:30 pmJackson-Evers Intl
4h 50m
1 stop
MDW7:20 pmChicago Midway
Sep 9
MDW2:40 pmChicago Midway
3h 25m
1 stop
JAN6:05 pmJackson-Evers Intl
$358
Southwest
Aug 13
JAN12:40 pmJackson-Evers Intl
6h 50m
2 stops
MDW7:30 pmChicago Midway
Aug 18
MDW7:50 amChicago Midway
5h 00m
1 stop
JAN12:50 pmJackson-Evers Intl
$364
Southwest
Jul 8
JAN7:15 pmJackson-Evers Intl
4h 40m
1 stop
MDW11:55 pmChicago Midway
Jul 9
MDW1:00 pmChicago Midway
9h 00m
2 stops
JAN10:00 pmJackson-Evers Intl
$368

Delta flights from Jackson, Mississippi to Chicago Midway Airport

Our best Delta deals on Jackson, Mississippi to Chicago Midway Airport flight tickets
Delta
Jul 8
JAN5:04 pmJackson-Evers Intl
5h 11m
1 stop
MDW10:15 pmChicago Midway
Jul 14
MDW6:00 amChicago Midway
4h 00m
1 stop
JAN10:00 amJackson-Evers Intl
$339
Delta
Aug 13
JAN3:30 pmJackson-Evers Intl
7h 06m
1 stop
MDW10:36 pmChicago Midway
Aug 18
MDW5:10 pmChicago Midway
6h 01m
1 stop
JAN11:11 pmJackson-Evers Intl
$359
Delta
Jul 8
JAN5:04 pmJackson-Evers Intl
5h 11m
1 stop
MDW10:15 pmChicago Midway
Jul 10
MDW5:10 pmChicago Midway
5h 59m
1 stop
JAN11:09 pmJackson-Evers Intl
$363

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 June 7, 2026.
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

Cheapest round-trip
Quickest round-trip

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 7/8

5:04 pm-10:15 pm

1 stop5h 11m

Chicago Midway

Tue 7/14

6:00 am-10:00 am

1 stop4h 00m

$339

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sat 7/4

6:00 am-12:15 pm

1 stop6h 15m

Chicago Midway

Sat 7/11

5:05 am-11:45 am

1 stop6h 40m

$358

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 8/13

3:30 pm-10:36 pm

1 stop7h 06m

Chicago Midway

Tue 8/18

5:10 pm-11:11 pm

1 stop6h 01m

$359

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sat 7/4

6:00 am-2:25 pm

2 stops8h 25m

Chicago Midway

Sat 7/11

5:05 am-11:45 am

1 stop6h 40m

$363

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 8/13

12:40 pm-7:30 pm

2 stops6h 50m

Chicago Midway

Tue 8/18

7:50 am-12:50 pm

1 stop5h 00m

$364

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 7/8

7:15 pm-11:55 pm

1 stop4h 40m

Chicago Midway

Thu 7/9

1:00 pm-10:00 pm

2 stops9h 00m

$368

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 8/13

12:40 pm-7:30 pm

2 stops6h 50m

Chicago Midway

Tue 8/18

6:00 am-12:50 pm

2 stops6h 50m

$369

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 7/8

3:06 pm-10:15 pm

1 stop7h 09m

Chicago Midway

Fri 7/10

5:10 pm-11:09 pm

1 stop5h 59m

$373

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 7/1

12:20 pm-5:05 pm

1 stop4h 45m

Chicago Midway

Tue 7/7

12:00 pm-8:45 pm

1 stop8h 45m

$374

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sat 8/22

6:00 am-1:00 pm

1 stop7h 00m

Chicago Midway

Mon 8/24

5:55 am-12:00 pm

1 stop6h 05m

$377

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 typical price of a round-trip flight between Jackson, Mississippi and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Jackson, Mississippi, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Jackson, Mississippi during the month January is also very affordable. Most momondo users find prices during this month for around $0.

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 11m

Direct flights

None
The fastest flight from Jackson, Mississippi to Chicago Midway Airport takes 4h 11m
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

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

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

    There are 668.7 mi between Jackson-Evers Intl and Chicago Midway. 4h 11m 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
8,395 reviews
Search Delta flights
SouthwestPriceFrom $234Free CancellationRating
8.0
4,257 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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