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Cheap flights from Jackson, Mississippi to Chicago from $152

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 5/23. 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
5:00 pm - 9:09 pm
JAN
-
MDW
4h 09m
1 stop
Delta Logo
6:05 am - 10:03 am
MDW
-
JAN
3h 58m
1 stop
$277Delta
Sat, Jun 6 - Tue, Jun 9
Southwest Logo
12:15 pm - 5:00 pm
JAN
-
MDW
4h 45m
1 stop
Southwest Logo
11:25 am - 6:45 pm
MDW
-
JAN
7h 20m
2 stops
$283Southwest
Sat, Jun 6 - Tue, Jun 9
Southwest Logo
12:15 pm - 10:25 pm
JAN
-
MDW
10h 10m
2 stops
Southwest Logo
11:25 am - 6:45 pm
MDW
-
JAN
7h 20m
2 stops
$288Southwest
Sat, Jun 6 - Tue, Jun 9
Delta Logo
2:55 pm - 9:09 pm
JAN
-
MDW
6h 14m
1 stop
Delta Logo
6:23 am - 12:43 pm
MDW
-
JAN
6h 20m
1 stop
$290Delta
Mon, May 18 - Wed, May 20
Delta Logo
2:40 pm - 9:46 pm
JAN
-
MDW
7h 06m
1 stop
Delta Logo
10:35 am - 3:53 pm
MDW
-
JAN
5h 18m
1 stop
$303Delta
Thu, Aug 20 - Sat, Aug 22
Southwest Logo
2:30 pm - 7:20 pm
JAN
-
MDW
4h 50m
1 stop
Southwest Logo
7:50 am - 12:50 pm
MDW
-
JAN
5h 00m
1 stop
$319Southwest
Sat, Aug 8 - Tue, Aug 11
Southwest Logo
1:00 pm - 4:45 pm
JAN
-
MDW
3h 45m
1 stop
Southwest Logo
7:25 am - 12:20 pm
MDW
-
JAN
4h 55m
1 stop
$320Southwest
Tue, May 19 - Tue, May 26
Southwest Logo
12:25 pm - 7:10 pm
JAN
-
MDW
6h 45m
2 stops
Southwest Logo
7:50 am - 12:50 pm
MDW
-
JAN
5h 00m
1 stop
$324Southwest
Sat, Aug 8 - Tue, Aug 11
Southwest Logo
1:00 pm - 4:45 pm
JAN
-
MDW
3h 45m
1 stop
Southwest Logo
11:35 am - 8:20 pm
MDW
-
JAN
8h 45m
2 stops
$325Southwest
Tue, May 19 - Tue, May 26
Delta Logo
5:05 pm - 9:09 pm
JAN
-
MDW
4h 04m
1 stop
Delta Logo
6:23 am - 12:12 pm
MDW
-
JAN
5h 49m
1 stop
$328Delta
Fri, May 29 - Mon, Jun 1

Delta flights from Jackson, Mississippi to Chicago Midway Airport

Our best Delta deals on Jackson, Mississippi to Chicago Midway Airport flight tickets
Delta
Jun 6
JAN5:00 pmJackson-Evers Intl
4h 09m
1 stop
MDW9:09 pmChicago Midway
Jun 9
MDW6:05 amChicago Midway
3h 58m
1 stop
JAN10:03 amJackson-Evers Intl
$277
Delta
May 18
JAN2:55 pmJackson-Evers Intl
6h 14m
1 stop
MDW9:09 pmChicago Midway
May 20
MDW6:23 amChicago Midway
6h 20m
1 stop
JAN12:43 pmJackson-Evers Intl
$290
Delta
Aug 20
JAN5:35 pmJackson-Evers Intl
4h 11m
1 stop
MDW9:46 pmChicago Midway
Aug 22
MDW10:35 amChicago Midway
5h 18m
1 stop
JAN3:53 pmJackson-Evers Intl
$303

Southwest flights from Jackson, Mississippi to Chicago Midway Airport

Our best Southwest deals on Jackson, Mississippi to Chicago Midway Airport flight tickets
Southwest
Jun 6
JAN12:15 pmJackson-Evers Intl
4h 45m
1 stop
MDW5:00 pmChicago Midway
Jun 9
MDW11:25 amChicago Midway
7h 20m
2 stops
JAN6:45 pmJackson-Evers Intl
$283
Southwest
Jun 6
JAN12:15 pmJackson-Evers Intl
10h 10m
2 stops
MDW10:25 pmChicago Midway
Jun 9
MDW11:25 amChicago Midway
7h 20m
2 stops
JAN6:45 pmJackson-Evers Intl
$288
Southwest
Aug 8
JAN2:30 pmJackson-Evers Intl
4h 50m
1 stop
MDW7:20 pmChicago Midway
Aug 11
MDW7:50 amChicago Midway
5h 00m
1 stop
JAN12:50 pmJackson-Evers Intl
$319

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 April 24, 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

Sat 6/6

5:00 pm-9:09 pm

1 stop4h 09m

Chicago Midway

Tue 6/9

6:05 am-10:03 am

1 stop3h 58m

$277

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sat 6/6

12:15 pm-5:00 pm

1 stop4h 45m

Chicago Midway

Tue 6/9

11:25 am-6:45 pm

2 stops7h 20m

$283

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sat 6/6

12:15 pm-10:25 pm

2 stops10h 10m

Chicago Midway

Tue 6/9

11:25 am-6:45 pm

2 stops7h 20m

$288

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Mon 5/18

2:55 pm-9:09 pm

1 stop6h 14m

Chicago Midway

Wed 5/20

6:23 am-12:43 pm

1 stop6h 20m

$290

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 8/20

2:40 pm-9:46 pm

1 stop7h 06m

Chicago Midway

Sat 8/22

10:35 am-3:53 pm

1 stop5h 18m

$303

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sat 8/8

2:30 pm-7:20 pm

1 stop4h 50m

Chicago Midway

Tue 8/11

7:50 am-12:50 pm

1 stop5h 00m

$319

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 5/19

1:00 pm-4:45 pm

1 stop3h 45m

Chicago Midway

Tue 5/26

7:25 am-12:20 pm

1 stop4h 55m

$320

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sat 8/8

12:25 pm-7:10 pm

2 stops6h 45m

Chicago Midway

Tue 8/11

7:50 am-12:50 pm

1 stop5h 00m

$324

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 5/19

1:00 pm-4:45 pm

1 stop3h 45m

Chicago Midway

Tue 5/26

11:35 am-8:20 pm

2 stops8h 45m

$325

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 5/29

5:05 pm-9:09 pm

1 stop4h 04m

Chicago Midway

Mon 6/1

6:23 am-12:12 pm

1 stop5h 49m

$328

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?

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 04m

Direct flights

None
The fastest flight from Jackson, Mississippi to Chicago Midway Airport takes 4h 04m
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 04m 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
8,455 reviews
Search Delta flights
SouthwestPriceFrom $234Free CancellationRating
8.0
4,334 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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