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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 3/25. 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

Enter your travel dates to find the best prices.
Delta Logo
5:02 pm - 10:28 pm
JAN
-
MDW
5h 26m
1 stop
Delta Logo
6:23 am - 12:44 pm
MDW
-
JAN
6h 21m
1 stop
$297Delta
Tue, May 5 - Tue, May 12
Southwest Logo
5:50 am - 10:45 am
JAN
-
MDW
4h 55m
1 stop
Southwest Logo
8:15 am - 5:30 pm
MDW
-
JAN
9h 15m
2 stops
$302Southwest
Wed, Apr 1 - Wed, Apr 8
Southwest Logo
6:30 am - 3:25 pm
JAN
-
MDW
8h 55m
2 stops
Southwest Logo
10:00 am - 7:15 pm
MDW
-
JAN
9h 15m
2 stops
$307Southwest
Tue, Apr 14 - Sat, Apr 18
Southwest Logo
6:30 am - 11:40 am
JAN
-
MDW
5h 10m
1 stop
Southwest Logo
5:00 am - 11:45 am
MDW
-
JAN
6h 45m
1 stop
$312Southwest
Wed, Apr 8 - Sat, Apr 11
Delta Logo
5:02 pm - 10:28 pm
JAN
-
MDW
5h 26m
1 stop
Delta Logo
6:23 am - 12:44 pm
MDW
-
JAN
6h 21m
1 stop
$317Delta
Tue, May 5 - Tue, May 12
Southwest Logo
6:30 am - 3:25 pm
JAN
-
MDW
8h 55m
2 stops
Southwest Logo
12:55 pm - 7:15 pm
MDW
-
JAN
6h 20m
2 stops
$322Southwest
Wed, Apr 8 - Sat, Apr 11
Southwest Logo
5:45 am - 10:25 am
JAN
-
MDW
4h 40m
1 stop
Southwest Logo
6:55 am - 11:40 am
MDW
-
JAN
4h 45m
1 stop
$327Southwest
Thu, Apr 16 - Mon, Apr 20
Southwest Logo
5:45 am - 10:25 am
JAN
-
MDW
4h 40m
1 stop
Southwest Logo
9:00 am - 7:05 pm
MDW
-
JAN
10h 05m
2 stops
$332Southwest
Thu, Apr 16 - Mon, Apr 20
Southwest Logo
12:05 pm - 8:50 pm
JAN
-
MDW
8h 45m
2 stops
Southwest Logo
8:15 am - 5:30 pm
MDW
-
JAN
9h 15m
2 stops
$338Southwest
Wed, Apr 1 - Wed, Apr 8
Southwest Logo
12:15 pm - 5:00 pm
JAN
-
MDW
4h 45m
1 stop
Southwest Logo
6:55 am - 11:40 am
MDW
-
JAN
4h 45m
1 stop
$347Southwest
Thu, Apr 16 - Mon, Apr 20

Southwest flights from Jackson, Mississippi to Chicago Midway Airport

Our best Southwest deals on Jackson, Mississippi to Chicago Midway Airport flight tickets
Southwest
Apr 1
JAN5:50 amJackson-Evers Intl
4h 55m
1 stop
MDW10:45 amChicago Midway
Apr 8
MDW8:15 amChicago Midway
9h 15m
2 stops
JAN5:30 pmJackson-Evers Intl
$302
Southwest
Apr 14
JAN6:30 amJackson-Evers Intl
8h 55m
2 stops
MDW3:25 pmChicago Midway
Apr 18
MDW10:00 amChicago Midway
9h 15m
2 stops
JAN7:15 pmJackson-Evers Intl
$307
Southwest
Apr 8
JAN6:30 amJackson-Evers Intl
5h 10m
1 stop
MDW11:40 amChicago Midway
Apr 11
MDW5:00 amChicago Midway
6h 45m
1 stop
JAN11:45 amJackson-Evers Intl
$312

Delta flights from Jackson, Mississippi to Chicago Midway Airport

Our best Delta deals on Jackson, Mississippi to Chicago Midway Airport flight tickets
Delta
May 5
JAN5:02 pmJackson-Evers Intl
5h 26m
1 stop
MDW10:28 pmChicago Midway
May 12
MDW6:23 amChicago Midway
6h 21m
1 stop
JAN12:44 pmJackson-Evers Intl
$297
Delta
May 5
JAN5:02 pmJackson-Evers Intl
5h 26m
1 stop
MDW10:28 pmChicago Midway
May 12
MDW6:23 amChicago Midway
6h 21m
1 stop
JAN12:44 pmJackson-Evers Intl
$317
Delta
Apr 17
JAN5:02 pmJackson-Evers Intl
5h 26m
1 stop
MDW10:28 pmChicago Midway
Apr 19
MDW6:00 amChicago Midway
4h 13m
1 stop
JAN10:13 amJackson-Evers Intl
$367

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 March 6, 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

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 5/5

5:02 pm-10:28 pm

1 stop5h 26m

Chicago Midway

Tue 5/12

6:23 am-12:44 pm

1 stop6h 21m

$297

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 4/1

5:50 am-10:45 am

1 stop4h 55m

Chicago Midway

Wed 4/8

8:15 am-5:30 pm

2 stops9h 15m

$302

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 4/14

6:30 am-3:25 pm

2 stops8h 55m

Chicago Midway

Sat 4/18

10:00 am-7:15 pm

2 stops9h 15m

$307

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 4/8

6:30 am-11:40 am

1 stop5h 10m

Chicago Midway

Sat 4/11

5:00 am-11:45 am

1 stop6h 45m

$312

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 5/5

5:02 pm-10:28 pm

1 stop5h 26m

Chicago Midway

Tue 5/12

6:23 am-12:44 pm

1 stop6h 21m

$317

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 4/8

6:30 am-3:25 pm

2 stops8h 55m

Chicago Midway

Sat 4/11

12:55 pm-7:15 pm

2 stops6h 20m

$322
Quickest round-trip

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 4/16

5:45 am-10:25 am

1 stop4h 40m

Chicago Midway

Mon 4/20

6:55 am-11:40 am

1 stop4h 45m

$327

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 4/16

5:45 am-10:25 am

1 stop4h 40m

Chicago Midway

Mon 4/20

9:00 am-7:05 pm

2 stops10h 05m

$332

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 4/1

12:05 pm-8:50 pm

2 stops8h 45m

Chicago Midway

Wed 4/8

8:15 am-5:30 pm

2 stops9h 15m

$338

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 4/16

12:15 pm-5:00 pm

1 stop4h 45m

Chicago Midway

Mon 4/20

6:55 am-11:40 am

1 stop4h 45m

$347

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 airline that flies from Jackson-Evers Intl to Chicago Midway?

Southwest and Delta are the most popular carriers operating from Jackson-Evers Intl to Chicago Midway

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

3h 45m

Direct flights

None
The fastest flight from Jackson, Mississippi to Chicago Midway Airport takes 3h 45m
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 45m 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
8,258 reviews
Search Delta flights
SouthwestPriceFrom $234Free CancellationRating
8.0
4,309 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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