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Cheap flights from Jackson, Mississippi to Chicago from $163

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 12/24. 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
12:11 pm - 4:44 pm
JAN
-
ORD
4h 33m1 stop
Delta Logo
8:00 am - 2:48 pm
ORD
-
JAN
6h 48m1 stop
$276Delta
Sat, Jan 10 - Sat, Jan 17
Delta Logo
12:11 pm - 4:44 pm
JAN
-
ORD
4h 33m1 stop
Delta Logo
2:50 pm - 9:50 pm
ORD
-
JAN
7h 00m1 stop
$291Delta
Tue, Jan 6 - Tue, Jan 13
Delta Logo
4:58 pm - 10:07 pm
JAN
-
MDW
5h 09m1 stop
Delta Logo
6:45 am - 11:17 am
MDW
-
JAN
4h 32m1 stop
$291Delta
Tue, Jan 6 - Tue, Jan 13
Delta Logo
12:11 pm - 4:45 pm
JAN
-
ORD
4h 34m1 stop
Delta Logo
5:59 pm - 11:01 pm
ORD
-
JAN
5h 02m1 stop
$311Delta
Wed, Jan 14 - Mon, Jan 19
Delta Logo
5:32 am - 10:27 am
JAN
-
MDW
4h 55m1 stop
Delta Logo
6:14 pm - 11:01 pm
MDW
-
JAN
4h 47m1 stop
$311Delta
Wed, Jan 14 - Mon, Jan 19
Southwest Logo
11:50 am - 6:10 pm
JAN
-
MDW
6h 20m1 stop
Southwest Logo
6:15 am - 12:40 pm
MDW
-
JAN
6h 25m1 stop
$317Southwest
Thu, Jan 15 - Thu, Jan 22
Southwest Logo
11:50 am - 6:10 pm
JAN
-
MDW
6h 20m1 stop
Southwest Logo
6:50 am - 2:40 pm
MDW
-
JAN
7h 50m2 stops
$322Southwest
Thu, Jan 15 - Thu, Jan 22
American Airlines Logo
9:16 am - 3:16 pm
JAN
-
ORD
6h 00m1 stop
American Airlines Logo
5:26 am - 12:12 pm
ORD
-
JAN
6h 46m1 stop
$388American Airlines
Tue, Mar 10 - Sat, Mar 14
United Airlines Logo
2:03 pm - 12:26 am
JAN
-
ORD
10h 23m1 stop
United Airlines Logo
5:45 am - 4:01 pm
ORD
-
JAN
10h 16m1 stop
$438United Airlines
Sat, Feb 14 - Wed, Feb 18
United Airlines Logo
2:03 pm - 12:26 am
JAN
-
ORD
10h 23m1 stop
United Airlines Logo
8:10 pm - 4:01 pm
ORD
-
JAN
19h 51m1 stop
$447United Airlines
Sat, Feb 14 - Wed, Feb 18

United Airlines flights from Jackson, Mississippi to Chicago

Our best United Airlines deals on Jackson, Mississippi to Chicago flight tickets
United Airlines
Feb 14
JAN2:03 pmJackson-Evers Intl
10h 23m
1 stop
ORD12:26 amChicago O'Hare Intl
Feb 18
ORD5:45 amChicago O'Hare Intl
10h 16m
1 stop
JAN4:01 pmJackson-Evers Intl
$438
Find similar
United Airlines
Feb 14
JAN2:03 pmJackson-Evers Intl
10h 23m
1 stop
ORD12:26 amChicago O'Hare Intl
Feb 18
ORD8:10 pmChicago O'Hare Intl
19h 51m
1 stop
JAN4:01 pmJackson-Evers Intl
$447
Find similar
United Airlines
Jan 10
JAN7:00 amJackson-Evers Intl
14h 25m
1 stop
ORD9:25 pmChicago O'Hare Intl
Jan 17
ORD7:40 pmChicago O'Hare Intl
17h 42m
2 stops
JAN1:22 pmJackson-Evers Intl
$493
Find similar

American Airlines flights from Jackson, Mississippi to Chicago

Our best American Airlines deals on Jackson, Mississippi to Chicago flight tickets
American Airlines
Dec 25
JAN5:10 amJackson-Evers Intl
5h 35m
1 stop
ORD10:45 amChicago O'Hare Intl
Dec 30
ORD6:37 pmChicago O'Hare Intl
5h 35m
1 stop
JAN12:12 amJackson-Evers Intl
$351
Find similar
American Airlines
Dec 25
JAN5:10 amJackson-Evers Intl
10h 17m
2 stops
ORD3:27 pmChicago O'Hare Intl
Dec 30
ORD6:37 pmChicago O'Hare Intl
5h 35m
1 stop
JAN12:12 amJackson-Evers Intl
$377
Find similar
American Airlines
Mar 10
JAN9:16 amJackson-Evers Intl
6h 00m
1 stop
ORD3:16 pmChicago O'Hare Intl
Mar 14
ORD5:26 amChicago O'Hare Intl
6h 46m
1 stop
JAN12:12 pmJackson-Evers Intl
$388
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Jackson, Mississippi to Chicago 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 December 16, 2025.
Use the filters below to find and compare flights from Jackson, Mississippi to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Sat 1/10

12:11 pm-4:44 pm

1 stop4h 33m

Chicago O'Hare Intl

Sat 1/17

8:00 am-2:48 pm

1 stop6h 48m

$276

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Tue 1/6

12:11 pm-4:44 pm

1 stop4h 33m

Chicago O'Hare Intl

Tue 1/13

2:50 pm-9:50 pm

1 stop7h 00m

$291

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 1/6

4:58 pm-10:07 pm

1 stop5h 09m

Chicago Midway

Tue 1/13

6:45 am-11:17 am

1 stop4h 32m

$291

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Wed 1/14

12:11 pm-4:45 pm

1 stop4h 34m

Chicago O'Hare Intl

Mon 1/19

5:59 pm-11:01 pm

1 stop5h 02m

$311

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 1/14

5:32 am-10:27 am

1 stop4h 55m

Chicago Midway

Mon 1/19

6:14 pm-11:01 pm

1 stop4h 47m

$311

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 1/15

11:50 am-6:10 pm

1 stop6h 20m

Chicago Midway

Thu 1/22

6:15 am-12:40 pm

1 stop6h 25m

$317

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Thu 1/15

11:50 am-6:10 pm

1 stop6h 20m

Chicago Midway

Thu 1/22

6:50 am-2:40 pm

2 stops7h 50m

$322

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Tue 3/10

9:16 am-3:16 pm

1 stop6h 00m

Chicago O'Hare Intl

Sat 3/14

5:26 am-12:12 pm

1 stop6h 46m

$388

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Sat 2/14

2:03 pm-12:26 am

1 stop10h 23m

Chicago O'Hare Intl

Wed 2/18

5:45 am-4:01 pm

1 stop10h 16m

$438

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Sat 2/14

2:03 pm-12:26 am

1 stop10h 23m

Chicago O'Hare Intl

Wed 2/18

8:10 pm-4:01 pm

1 stop19h 51m

$447

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

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?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Jackson, Mississippi, with most prices found around $301. If you’re not able to fly to Chicago in September, then December is your next best option. Flight prices from Jackson, Mississippi to Chicago during December average around $321.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $376. This is often the case because there is less demand to fly during this day of the week. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Jackson, Mississippi to Chicago for around $544.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Jackson, Mississippi to Chicago during this time can be as low as $362. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $597.

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

As of December 2025, prices for Jackson, Mississippi to Chicago flights are approximately 97% more expensive when compared to flights at the same time last year.

When to book flights from Jackson, Mississippi to Chicago

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

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

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

Fastest flight time

3h 40m

Direct flights

None
The fastest flight from Jackson, Mississippi to Chicago takes 3h 40m
There are no direct flights from Jackson, Mississippi to Chicago. There are no popular flight routes from Jackson, Mississippi to Chicago.
Search flight deals

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

    The distance between Jackson-Evers Intl and Chicago is about 676.0 mi. By plane, this route typically takes 3h 40m.

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

    Prices for flights from Jackson-Evers Intl Airport to Chicago were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Jackson-Evers Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Jackson, Mississippi to Chicago?

Best airlines flying from Jackson, Mississippi to Chicago

Compare and see reviews for airlines that fly from Jackson, Mississippi to Chicago with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $196Free CancellationRating
7.9
8,008 reviews
Search Delta flights
SouthwestPriceFrom $234Free CancellationRating
7.9
4,250 reviews
Search Southwest flights
American AirlinesPriceFrom $258Free CancellationRating
7.2
11,049 reviews
Search American Airlines flights

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Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Jackson to Chicago for you.

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

momondo does allow users to show only those flights to Chicago from Jackson which offer a flexible booking policy as well as other useful filters and features.

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?

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

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport