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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 2/28. 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
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 - 11:59 pm
JAN
-
ORD
6h 57m
1 stop
Delta Logo
6:00 am - 10:04 am
ORD
-
JAN
4h 04m
1 stop
$303Delta
Tue, May 5 - Tue, May 12
Delta Logo
5:02 pm - 10:28 pm
JAN
-
MDW
5h 26m
1 stop
Delta Logo
6:30 am - 12:13 pm
MDW
-
JAN
5h 43m
1 stop
$303Delta
Tue, May 5 - Tue, May 12
Southwest Logo
6:20 pm - 11:05 pm
JAN
-
MDW
4h 45m
1 stop
Southwest Logo
5:00 am - 11:45 am
MDW
-
JAN
6h 45m
1 stop
$314Southwest
Tue, May 5 - Sat, May 9
Southwest Logo
6:20 pm - 11:05 pm
JAN
-
MDW
4h 45m
1 stop
Southwest Logo
12:55 pm - 7:15 pm
MDW
-
JAN
6h 20m
2 stops
$319Southwest
Tue, May 5 - Sat, May 9
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
$324Southwest
Tue, May 5 - Sat, May 9
Delta Logo
10:59 am - 4:42 pm
JAN
-
ORD
5h 43m
1 stop
Delta Logo
6:00 am - 10:04 am
ORD
-
JAN
4h 04m
1 stop
$325Delta
Tue, May 5 - Tue, May 12
Delta Logo
5:02 pm - 10:28 pm
JAN
-
MDW
5h 26m
1 stop
Delta Logo
6:30 am - 12:13 pm
MDW
-
JAN
5h 43m
1 stop
$325Delta
Tue, May 5 - Tue, May 12
American Airlines Logo
6:35 am - 1:19 pm
JAN
-
ORD
6h 44m
1 stop
American Airlines Logo
6:10 am - 11:57 am
ORD
-
JAN
5h 47m
1 stop
$332American Airlines
Wed, Mar 4 - Wed, Mar 11
American Airlines Logo
5:30 am - 1:04 pm
JAN
-
ORD
7h 34m
1 stop
American Airlines Logo
7:12 am - 12:40 pm
ORD
-
JAN
5h 28m
1 stop
$356American Airlines
Sat, Mar 28 - Wed, Apr 1
American Airlines Logo
6:42 pm - 12:16 am
JAN
-
ORD
5h 34m
1 stop
American Airlines Logo
7:00 am - 11:57 am
ORD
-
JAN
4h 57m
1 stop
$367American Airlines
Fri, Mar 13 - Tue, Mar 17

United Airlines flights from Jackson, Mississippi to Chicago

Our best United Airlines deals on Jackson, Mississippi to Chicago flight tickets
United Airlines
Apr 10
JAN4:57 pmJackson-Evers Intl
16h 38m
2 stops
ORD9:35 amChicago O'Hare Intl
Apr 12
ORD5:48 amChicago O'Hare Intl
7h 35m
1 stop
JAN1:23 pmJackson-Evers Intl
$574
United Airlines
Feb 14
JAN2:03 pmJackson-Evers Intl
19h 34m
2 stops
ORD9:37 amChicago O'Hare Intl
Feb 18
ORD8:13 pmChicago O'Hare Intl
17h 13m
2 stops
JAN1:26 pmJackson-Evers Intl
$605
United Airlines
Feb 14
JAN2:03 pmJackson-Evers Intl
7h 25m
1 stop
ORD9:28 pmChicago O'Hare Intl
Feb 18
ORD8:13 pmChicago O'Hare Intl
17h 13m
2 stops
JAN1:26 pmJackson-Evers Intl
$607

American Airlines flights from Jackson, Mississippi to Chicago

Our best American Airlines deals on Jackson, Mississippi to Chicago flight tickets
American Airlines
Mar 4
JAN6:35 amJackson-Evers Intl
6h 44m
1 stop
ORD1:19 pmChicago O'Hare Intl
Mar 11
ORD6:10 amChicago O'Hare Intl
5h 47m
1 stop
JAN11:57 amJackson-Evers Intl
$332
American Airlines
Mar 28
JAN5:30 amJackson-Evers Intl
7h 34m
1 stop
ORD1:04 pmChicago O'Hare Intl
Apr 1
ORD7:12 amChicago O'Hare Intl
5h 28m
1 stop
JAN12:40 pmJackson-Evers Intl
$356
American Airlines
Mar 13
JAN6:42 pmJackson-Evers Intl
5h 34m
1 stop
ORD12:16 amChicago O'Hare Intl
Mar 17
ORD7:00 amChicago O'Hare Intl
4h 57m
1 stop
JAN11:57 amJackson-Evers Intl
$367

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 February 3, 2026.
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

Tue 5/5

5:02 pm-11:59 pm

1 stop6h 57m

Chicago O'Hare Intl

Tue 5/12

6:00 am-10:04 am

1 stop4h 04m

$303

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 5/5

5:02 pm-10:28 pm

1 stop5h 26m

Chicago Midway

Tue 5/12

6:30 am-12:13 pm

1 stop5h 43m

$303

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 5/5

6:20 pm-11:05 pm

1 stop4h 45m

Chicago Midway

Sat 5/9

5:00 am-11:45 am

1 stop6h 45m

$314

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 5/5

6:20 pm-11:05 pm

1 stop4h 45m

Chicago Midway

Sat 5/9

12:55 pm-7:15 pm

2 stops6h 20m

$319

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 5/5

6:30 am-3:25 pm

2 stops8h 55m

Chicago Midway

Sat 5/9

12:55 pm-7:15 pm

2 stops6h 20m

$324

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Tue 5/5

10:59 am-4:42 pm

1 stop5h 43m

Chicago O'Hare Intl

Tue 5/12

6:00 am-10:04 am

1 stop4h 04m

$325

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 5/5

5:02 pm-10:28 pm

1 stop5h 26m

Chicago Midway

Tue 5/12

6:30 am-12:13 pm

1 stop5h 43m

$325

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Wed 3/4

6:35 am-1:19 pm

1 stop6h 44m

Chicago O'Hare Intl

Wed 3/11

6:10 am-11:57 am

1 stop5h 47m

$332

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Sat 3/28

5:30 am-1:04 pm

1 stop7h 34m

Chicago O'Hare Intl

Wed 4/1

7:12 am-12:40 pm

1 stop5h 28m

$356

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Fri 3/13

6:42 pm-12:16 am

1 stop5h 34m

Chicago O'Hare Intl

Tue 3/17

7:00 am-11:57 am

1 stop4h 57m

$367

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 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 August is your next best option. Flight prices from Jackson, Mississippi to Chicago during August average around $342.

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

As of February 2026, prices for Jackson, Mississippi to Chicago flights are approximately 13% 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

4h 06m

Direct flights

None
The fastest flight from Jackson, Mississippi to Chicago takes 4h 06m
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 4h 06m.

  • 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
8,132 reviews
Search Delta flights
SouthwestPriceFrom $234Free CancellationRating
8.0
4,271 reviews
Search Southwest flights
American AirlinesPriceFrom $258Free CancellationRating
7.2
11,212 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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Porter
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Saint John

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