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Cheap flights from Chicago to Jackson 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 Chicago to Jackson departing on 10/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago to Jackson

Cheap round-trip flights

Southwest Logo
8:40 am - 3:25 pmMDW-JAN
6h 45m1 stop
Southwest Logo
3:20 pm - 10:25 pmJAN-MDW
7h 05m1 stop
$263Southwest
Find Deal
Tue, Oct 14 - Sat, Oct 18
Delta Logo
6:45 am - 12:16 pmORD-JAN
5h 31m1 stop
Delta Logo
7:18 pm - 11:58 pmJAN-ORD
4h 40m1 stop
$287Delta
Find Deal
Wed, Oct 22 - Mon, Oct 27
Southwest Logo
8:40 am - 3:25 pmMDW-JAN
6h 45m1 stop
Southwest Logo
8:05 pm - 12:45 amJAN-MDW
4h 40m1 stop
$287Southwest
Find Deal
Wed, Oct 29 - Thu, Oct 30
Southwest Logo
10:00 am - 6:25 pmMDW-JAN
8h 25m2 stops
Southwest Logo
8:05 pm - 12:45 amJAN-MDW
4h 40m1 stop
$292Southwest
Find Deal
Wed, Oct 29 - Thu, Oct 30
Delta Logo
6:45 am - 12:16 pmORD-JAN
5h 31m1 stop
Delta Logo
5:58 pm - 11:58 pmJAN-ORD
6h 00m1 stop
$297Delta
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Sat, Oct 18 - Mon, Oct 20
Delta Logo
6:00 am - 10:01 amMDW-JAN
4h 01m1 stop
Delta Logo
5:58 pm - 10:14 pmJAN-MDW
4h 16m1 stop
$297Delta
Find Deal
Sat, Oct 18 - Sat, Oct 25
American Airlines Logo
5:17 pm - 10:31 pmORD-JAN
5h 14m1 stop
American Airlines Logo
4:28 pm - 11:53 pmJAN-ORD
7h 25m1 stop
$312American Airlines
Find Deal
Fri, Oct 24 - Sat, Oct 25
American Airlines Logo
6:45 am - 12:39 pmORD-JAN
5h 54m1 stop
American Airlines Logo
6:43 pm - 11:53 pmJAN-ORD
5h 10m1 stop
$318American Airlines
Find Deal
Wed, Oct 15 - Thu, Oct 16
United Airlines Logo
8:50 am - 7:41 pmORD-JAN
10h 51m1 stop
United Airlines Logo
5:18 pm - 9:29 amJAN-ORD
16h 11m2 stops
$448United Airlines
Find Deal
Tue, Nov 18 - Sun, Nov 23
United Airlines Logo
11:10 am - 9:58 pmORD-JAN
10h 48m2 stops
United Airlines Logo
12:00 pm - 12:14 amJAN-ORD
12h 14m1 stop
$488United Airlines
Find Deal
Wed, Oct 15 - Thu, Oct 16

American Airlines flights from Chicago to Jackson, Mississippi

Our best American Airlines deals on Chicago to Jackson, Mississippi flight tickets
American Airlines
Oct 24
ORD5:17 pmChicago O'Hare Intl
5h 14m
1 stop
JAN10:31 pmJackson-Evers Intl
Oct 25
JAN4:28 pmJackson-Evers Intl
7h 25m
1 stop
ORD11:53 pmChicago O'Hare Intl
$312
Find similar
American Airlines
Oct 15
ORD6:45 amChicago O'Hare Intl
5h 54m
1 stop
JAN12:39 pmJackson-Evers Intl
Oct 16
JAN6:43 pmJackson-Evers Intl
5h 10m
1 stop
ORD11:53 pmChicago O'Hare Intl
$318
Find similar
American Airlines
Oct 16
ORD5:00 amChicago O'Hare Intl
7h 40m
1 stop
JAN12:40 pmJackson-Evers Intl
Oct 20
JAN4:28 pmJackson-Evers Intl
7h 25m
1 stop
ORD11:53 pmChicago O'Hare Intl
$328
Find similar

Southwest flights from Chicago to Jackson, Mississippi

Our best Southwest deals on Chicago to Jackson, Mississippi flight tickets
Southwest
Oct 14
MDW8:40 amChicago Midway
6h 45m
1 stop
JAN3:25 pmJackson-Evers Intl
Oct 18
JAN3:20 pmJackson-Evers Intl
7h 05m
1 stop
MDW10:25 pmChicago Midway
$263
Find similar
Southwest
Oct 29
MDW8:40 amChicago Midway
6h 45m
1 stop
JAN3:25 pmJackson-Evers Intl
Oct 30
JAN8:05 pmJackson-Evers Intl
4h 40m
1 stop
MDW12:45 amChicago Midway
$287
Find similar
Southwest
Oct 29
MDW10:00 amChicago Midway
8h 25m
2 stops
JAN6:25 pmJackson-Evers Intl
Oct 30
JAN8:05 pmJackson-Evers Intl
4h 40m
1 stop
MDW12:45 amChicago Midway
$292
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Jackson, Mississippi 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 September 15, 2025.
Use the filters below to find and compare flights from Chicago to Jackson, Mississippi that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Tue 10/14

8:40 am-3:25 pm

1 stop6h 45m

Jackson-Evers Intl

Sat 10/18

3:20 pm-10:25 pm

1 stop7h 05m

$263

ChicagoJackson

ORD - JAN

ORDJAN

Chicago O'Hare Intl

Wed 10/22

6:45 am-12:16 pm

1 stop5h 31m

Jackson-Evers Intl

Mon 10/27

7:18 pm-11:58 pm

1 stop4h 40m

$287

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Wed 10/29

8:40 am-3:25 pm

1 stop6h 45m

Jackson-Evers Intl

Thu 10/30

8:05 pm-12:45 am

1 stop4h 40m

$287

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Wed 10/29

10:00 am-6:25 pm

2 stops8h 25m

Jackson-Evers Intl

Thu 10/30

8:05 pm-12:45 am

1 stop4h 40m

$292

ChicagoJackson

ORD - JAN

ORDJAN

Chicago O'Hare Intl

Sat 10/18

6:45 am-12:16 pm

1 stop5h 31m

Jackson-Evers Intl

Mon 10/20

5:58 pm-11:58 pm

1 stop6h 00m

$297

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 10/18

6:00 am-10:01 am

1 stop4h 01m

Jackson-Evers Intl

Sat 10/25

5:58 pm-10:14 pm

1 stop4h 16m

$297

ChicagoJackson

ORD - JAN

ORDJAN

Chicago O'Hare Intl

Fri 10/24

5:17 pm-10:31 pm

1 stop5h 14m

Jackson-Evers Intl

Sat 10/25

4:28 pm-11:53 pm

1 stop7h 25m

$312

ChicagoJackson

ORD - JAN

ORDJAN

Chicago O'Hare Intl

Wed 10/15

6:45 am-12:39 pm

1 stop5h 54m

Jackson-Evers Intl

Thu 10/16

6:43 pm-11:53 pm

1 stop5h 10m

$318

ChicagoJackson

ORD - JAN

ORDJAN

Chicago O'Hare Intl

Tue 11/18

8:50 am-7:41 pm

1 stop10h 51m

Jackson-Evers Intl

Sun 11/23

5:18 pm-9:29 am

2 stops16h 11m

$448

ChicagoJackson

ORD - JAN

ORDJAN

Chicago O'Hare Intl

Wed 10/15

11:10 am-9:58 pm

2 stops10h 48m

Jackson-Evers Intl

Thu 10/16

12:00 pm-12:14 am

1 stop12h 14m

$488

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 Jackson from

How to get the cheapest flight ticket from Chicago to Jackson, Mississippi

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 month to fly to Jackson, Mississippi?

The cheapest month to fly to Jackson, Mississippi from Chicago is in October. Flight prices, which tend to average around $286, are often lower during this time because this is during the off-season. If you’re not able to fly to Jackson, Mississippi in October, then June is your next best option. Flight prices from Chicago to Jackson, Mississippi during June average around $323.

What is the cheapest day to depart on your flight to Jackson, Mississippi?

The cheapest day to depart from Chicago to Jackson, Mississippi is on a Wednesday when prices can be found for as low as $320. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $496.

What is the cheapest time of day to depart on your flight to Jackson, Mississippi?

Our most recent data shows that the best time of day to fly to Jackson, Mississippi is in the afternoon. Flights from Chicago to Jackson, Mississippi during this time can be as low as $386. In contrast, the most expensive time of day to depart to Jackson, Mississippi is at noon when prices are around $436.

How have Chicago to Jackson, Mississippi flight prices changed over time?

As of September 2025, prices for Chicago to Jackson, Mississippi flights are approximately 68% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Jackson, Mississippi

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Jackson, Mississippi according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Jackson, Mississippi (CHI to JAN) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Jackson, Mississippi

Direct flights

None
There are no direct flights from Chicago to Jackson, Mississippi. There are no popular flight routes from Chicago to Jackson, Mississippi.
Search flight deals

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

    Jackson-Evers Intl is 676.0 mi away from Chicago. In terms of flight time, this usually takes a little over 3h 30m.

  • When did momondo last update prices for flights from Chicago to Jackson-Evers Intl Airport?

    Prices for flights from Chicago to Jackson-Evers Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago to Jackson-Evers Intl Airport?

  • How old do you have to be to fly from Chicago to Jackson-Evers Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Jackson-Evers Intl Airport.

  • What documentation or ID do you need to fly to Jackson-Evers Intl Airport?

    The travel and health documents you'll need for your trip to Jackson-Evers Intl 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 Jackson-Evers Intl 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 Chicago to Jackson, Mississippi?

Best airlines flying from Chicago to Jackson, Mississippi

Compare and see reviews for airlines that fly from Chicago to Jackson, Mississippi with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $248Free CancellationRating
7.9
7,954 reviews
Search Delta flights
American AirlinesPriceFrom $256Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $316Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
United AirlinesPriceFrom $356Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights

Traveling to a place near Jackson?

Book flights to Jackson if you plan to visit one of these locations
Vicksburg
Flowood
Clinton
Pearl
Brandon
Richland

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Jackson?

Finding the right flight to Jackson from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Jackson quick and easy, saving you time and money.

Can I find flights from Chicago to Jackson with flexible booking policies on momondo?

Yes. All flights to Jackson from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Jackson?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Jackson from Chicago.

I’m not ready to book a flight from Chicago to Jackson right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Jackson now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Jackson and let you know when they change.

An easier way to manage your Jackson, Mississippi trip

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