Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Jackson, Mississippi to Chicago from $155

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Jackson, Mississippi to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
11:10 am - 4:14 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
5h 04m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 11:49 amMDW  Chicago Midway-JAN Jackson-Evers Intl
5h 45m1 stop Atlanta Hartsfield-Jackson
$309Delta
Thu, Oct 29 - Mon, Nov 2
Delta Logo
5:14 pm - 10:44 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
5h 30m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 10:23 amMDW  Chicago Midway-JAN Jackson-Evers Intl
4h 18m1 stop Atlanta Hartsfield-Jackson
$309Delta
Sat, Sep 26 - Wed, Sep 30
Southwest Logo
11:45 am - 4:10 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
4h 25m1 stop Nashville Intl
Southwest Logo
5:15 am - 11:05 amMDW  Chicago Midway-JAN Jackson-Evers Intl
5h 50m1 stop Houston Hobby
$309Southwest
Mon, Nov 2 - Thu, Nov 5
Southwest Logo
6:40 pm - 11:15 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
4h 35m1 stop Houston Hobby
Southwest Logo
5:25 am - 12:00 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
6h 35m1 stop Houston Hobby
$309Southwest
Tue, Sep 22 - Mon, Sep 28
American Airlines Logo
12:21 pm - 8:30 pmJAN  Jackson-Evers Intl-ORD Chicago O'Hare Intl
8h 09m1 stop Dallas/Fort Worth
American Airlines Logo
11:00 am - 6:50 pmORD  Chicago O'Hare Intl-JAN Jackson-Evers Intl
7h 50m1 stop Dallas/Fort Worth
$309American Airlines
Sat, Sep 26 - Wed, Sep 30
American Airlines Logo
5:00 am - 11:02 amJAN  Jackson-Evers Intl-ORD Chicago O'Hare Intl
6h 02m1 stop Charlotte Douglas
American Airlines Logo
1:22 pm - 9:20 pmORD  Chicago O'Hare Intl-JAN Jackson-Evers Intl
7h 58m1 stop Charlotte Douglas
$309American Airlines
Thu, Nov 5 - Mon, Nov 9
Delta Logo
5:14 pm - 10:44 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
5h 30m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 11:46 amMDW  Chicago Midway-JAN Jackson-Evers Intl
5h 41m1 stop Atlanta Hartsfield-Jackson
$309Delta
Wed, Sep 30 - Sat, Oct 3
American Airlines Logo
9:24 am - 4:16 pmJAN  Jackson-Evers Intl-ORD Chicago O'Hare Intl
6h 52m1 stop Dallas/Fort Worth
American Airlines Logo
6:41 am - 11:56 amORD  Chicago O'Hare Intl-JAN Jackson-Evers Intl
5h 15m1 stop Charlotte Douglas
$309American Airlines
Thu, Oct 29 - Mon, Nov 2
United Airlines Logo
5:20 pm - 11:27 amJAN  Jackson-Evers Intl-ORD Chicago O'Hare Intl
18h 07m1 stop Houston George Bush Intcntl
United Airlines Logo
8:00 pm - 11:13 amORD  Chicago O'Hare Intl-JAN Jackson-Evers Intl
15h 13m1 stop Houston George Bush Intcntl
$465United Airlines
Tue, Feb 2 - Wed, Feb 3
United Airlines Logo
7:00 am - 9:11 pmJAN  Jackson-Evers Intl-ORD Chicago O'Hare Intl
14h 11m1 stop Houston George Bush Intcntl
United Airlines Logo
9:30 pm - 11:13 amORD  Chicago O'Hare Intl-JAN Jackson-Evers Intl
13h 43m1 stop Houston George Bush Intcntl
$465United Airlines
Tue, Feb 2 - Wed, Feb 3

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Delta flights from Jackson, Mississippi to Chicago

Our best Delta deals on Jackson, Mississippi to Chicago flight tickets
Delta
Sep 15
JAN5:14 pmJackson-Evers Intl
6h 45m
1 stop
ORD11:59 pmChicago O'Hare Intl
Oct 13
ORD5:27 amChicago O'Hare Intl
4h 58m
1 stop
JAN10:25 amJackson-Evers Intl
$309
Delta
Sep 25
JAN7:04 pmJackson-Evers Intl
4h 55m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 28
ORD5:30 amChicago O'Hare Intl
6h 47m
1 stop
JAN12:17 pmJackson-Evers Intl
$322
Delta
Sep 30
JAN7:51 amJackson-Evers Intl
4h 03m
1 stop
MDW11:54 amChicago Midway
Sep 30
MDW5:11 pmChicago Midway
6h 10m
1 stop
JAN11:21 pmJackson-Evers Intl
$351

American Airlines flights from Jackson, Mississippi to Chicago

Our best American Airlines deals on Jackson, Mississippi to Chicago flight tickets
American Airlines
Sep 17
JAN4:33 pmJackson-Evers Intl
7h 41m
1 stop
ORD12:14 amChicago O'Hare Intl
Oct 13
ORD3:50 pmChicago O'Hare Intl
5h 02m
1 stop
JAN8:52 pmJackson-Evers Intl
$331
American Airlines
Sep 21
JAN5:02 pmJackson-Evers Intl
7h 12m
1 stop
ORD12:14 amChicago O'Hare Intl
Sep 22
ORD8:05 amChicago O'Hare Intl
6h 47m
1 stop
JAN2:52 pmJackson-Evers Intl
$387
American Airlines
Oct 8
JAN6:45 pmJackson-Evers Intl
5h 23m
1 stop
ORD12:08 amChicago O'Hare Intl
Oct 13
ORD1:46 pmChicago O'Hare Intl
7h 06m
1 stop
JAN8:52 pmJackson-Evers Intl
$396

momondo Fare Finder

 
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

Cheapest round-trip

JacksonChicago

JAN Jackson-Evers Intl - MDW Chicago Midway

JANMDW

Jackson-Evers Intl

Thu 10/29

11:10 am-4:14 pm

1 stop5h 04m

Chicago Midway

Mon 11/2

6:04 am-11:49 am

1 stop5h 45m

$309
Quickest round-trip

JacksonChicago

JAN Jackson-Evers Intl - MDW Chicago Midway

JANMDW

Jackson-Evers Intl

Sat 9/26

5:14 pm-10:44 pm

1 stop5h 30m

Chicago Midway

Wed 9/30

6:05 am-10:23 am

1 stop4h 18m

$309

JacksonChicago

JAN Jackson-Evers Intl - MDW Chicago Midway

JANMDW

Jackson-Evers Intl

Mon 11/2

11:45 am-4:10 pm

1 stop4h 25m

Chicago Midway

Thu 11/5

5:15 am-11:05 am

1 stop5h 50m

$309

JacksonChicago

JAN Jackson-Evers Intl - MDW Chicago Midway

JANMDW

Jackson-Evers Intl

Tue 9/22

6:40 pm-11:15 pm

1 stop4h 35m

Chicago Midway

Mon 9/28

5:25 am-12:00 pm

1 stop6h 35m

$309

JacksonChicago

JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl

JANORD

Jackson-Evers Intl

Sat 9/26

12:21 pm-8:30 pm

1 stop8h 09m

Chicago O'Hare Intl

Wed 9/30

11:00 am-6:50 pm

1 stop7h 50m

$309

JacksonChicago

JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl

JANORD

Jackson-Evers Intl

Thu 11/5

5:00 am-11:02 am

1 stop6h 02m

Chicago O'Hare Intl

Mon 11/9

1:22 pm-9:20 pm

1 stop7h 58m

$309

JacksonChicago

JAN Jackson-Evers Intl - MDW Chicago Midway

JANMDW

Jackson-Evers Intl

Wed 9/30

5:14 pm-10:44 pm

1 stop5h 30m

Chicago Midway

Sat 10/3

6:05 am-11:46 am

1 stop5h 41m

$309

JacksonChicago

JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl

JANORD

Jackson-Evers Intl

Thu 10/29

9:24 am-4:16 pm

1 stop6h 52m

Chicago O'Hare Intl

Mon 11/2

6:41 am-11:56 am

1 stop5h 15m

$309

JacksonChicago

JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl

JANORD

Jackson-Evers Intl

Tue 2/2

5:20 pm-11:27 am

1 stop18h 07m

Chicago O'Hare Intl

Wed 2/3

8:00 pm-11:13 am

1 stop15h 13m

$465

JacksonChicago

JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl

JANORD

Jackson-Evers Intl

Tue 2/2

7:00 am-9:11 pm

1 stop14h 11m

Chicago O'Hare Intl

Wed 2/3

9:30 pm-11:13 am

1 stop13h 43m

$465

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 October is, on average, the cheapest month to fly to Chicago from Jackson, Mississippi, with most prices found around $321. If you’re not able to fly to Chicago in October, then January is your next best option. Flight prices from Jackson, Mississippi to Chicago during January average around $345.

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

As of August 2026, prices for Jackson, Mississippi to Chicago flights are approximately 28% 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

Best Price Found

$155

Fastest flight time

4h 25m

Direct flights

None
The best one-way flight to Chicago from Jackson, Mississippi in the past 72 hours is $155. The best round-trip flight deal from Jackson, Mississippi to Chicago found on momondo in the last 72 hours is $309.
The fastest flight from Jackson, Mississippi to Chicago takes 4h 25m
There are no direct flights from Jackson, Mississippi to Chicago. There are no popular flight routes from Jackson, Mississippi to Chicago.
Search flight deals

Frequently asked questions about flying from Jackson, Mississippi to Chicago

  • 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 25m.

  • 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 $249Free CancellationRating
7.8
8,520 reviews
Search Delta flights
American AirlinesPriceFrom $296Free CancellationRating
7.1
11,986 reviews
Search American Airlines flights
SouthwestPriceFrom $308Free CancellationRating
8.0
4,209 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
Griffith
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 9/24
Thu 10/1
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport