CHI - JAN

$177 Find Cheap Flights from Chicago to Jackson

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Jackson departing on 5/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Jackson

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Jackson, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Jackson, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$251
Typical prices: $696-$332
American Airlines
Wed 4/22Wed 4/29
ORD - JAN • 1 stop
Cheapest one-way
$177
American Airlines
Fri 5/8
ORD - JAN • 1 stop
Top airlines
Cheapest • from $251 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Jackson. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $349 (round-trip)
Shortest trip • 3h 39m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 30% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Jackson!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Jackson (CHI-JAN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Jackson that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Jackson

Wed, Apr 22 - Wed, Apr 29
American Airlines Logo
6:41 pm - 11:59 pm
ORD
-
JAN
5h 18m
1 stop
American Airlines Logo
1:58 pm - 7:22 pm
JAN
-
ORD
5h 24m
1 stop
$251American Airlines
Tue, May 5 - Wed, May 13
Delta Logo
6:00 am - 12:08 pm
MDW
-
JAN
6h 08m
1 stop
Delta Logo
5:00 pm - 9:09 pm
JAN
-
MDW
4h 09m
1 stop
$251Delta
Wed, May 6 - Tue, May 12
Southwest Logo
10:10 am - 5:30 pm
MDW
-
JAN
7h 20m
2 stops
Southwest Logo
6:20 pm - 11:05 pm
JAN
-
MDW
4h 45m
1 stop
$256Southwest
Wed, Apr 22 - Sat, Apr 25
American Airlines Logo
6:41 pm - 11:59 pm
ORD
-
JAN
5h 18m
1 stop
American Airlines Logo
2:20 pm - 10:00 pm
JAN
-
ORD
7h 40m
1 stop
$277American Airlines
Wed, Apr 22 - Sat, Apr 25
Delta Logo
6:00 am - 10:13 am
MDW
-
JAN
4h 13m
1 stop
Delta Logo
5:36 am - 9:56 am
JAN
-
MDW
4h 20m
1 stop
$277Delta
Wed, Apr 22 - Sat, Apr 25
Southwest Logo
7:25 am - 12:20 pm
MDW
-
JAN
4h 55m
1 stop
Southwest Logo
12:20 pm - 10:35 pm
JAN
-
MDW
10h 15m
2 stops
$282Southwest
Wed, Apr 22 - Sat, Apr 25
Southwest Logo
11:55 am - 8:20 pm
ORD
-
JAN
8h 25m
2 stops
Southwest Logo
12:20 pm - 9:55 pm
JAN
-
ORD
9h 35m
2 stops
$287Southwest
Wed, Apr 22 - Sat, Apr 25
Southwest Logo
10:10 am - 5:30 pm
MDW
-
JAN
7h 20m
2 stops
Southwest Logo
6:00 am - 12:10 pm
JAN
-
MDW
6h 10m
2 stops
$287Southwest
Thu, Apr 16 - Sat, Apr 18
Delta Logo
5:15 am - 10:13 am
ORD
-
JAN
4h 58m
1 stop
Delta Logo
5:02 pm - 11:59 pm
JAN
-
ORD
6h 57m
1 stop
$303Delta
Mon, May 4 - Mon, May 11
Delta Logo
6:00 am - 12:08 pm
MDW
-
JAN
6h 08m
1 stop
Delta Logo
5:00 pm - 9:09 pm
JAN
-
MDW
4h 09m
1 stop
$303Delta
Booking Insights

KAYAK's insights & trends for Chicago to Jackson flights

Get data-powered insights and trends into flights from Chicago to Jackson to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Jackson, Mississippi?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Jackson, Mississippi departing in April.

What is the cheapest month to fly from Chicago to Jackson?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Jackson, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Jackson is June, where tickets cost $323 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $756 and $576 respectively.

Good to know

Low seasonNovember
Cheapest flight$177
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Chicago O'Hare Airport to Jackson

When to book flights from Chicago to Jackson

Are your dates flexible? Find out the best times to travel from Chicago to Jackson based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Jackson

  • What is the cheapest flight from Chicago to Jackson?

    In the last 3 days, the lowest price for a flight from Chicago to Jackson was $177 for a one-way ticket and $251 for a round-trip.

  • Do I need a passport to fly between Chicago and Jackson?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Chicago to Jackson?

    On your way to Jackson, you’ll fly out from one of these Chicago airports: Chicago Midway or Chicago O'Hare Intl. You’ll be landing at Jackson-Evers Intl.

  • Which aircraft models fly most regularly from Chicago to Jackson?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Jackson?

    oneworld, and SkyTeam are the airline alliances operating flights between Chicago and Jackson, with oneworld being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to Jackson, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Jackson are Southwest and Delta. With an average price for the route of $492 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $502 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Chicago to Jackson?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Jackson.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Jackson?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Jackson from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Jackson?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Jackson with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Jackson?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Jackson from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Chicago to Jackson

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Jackson. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Jackson? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4333 reviews
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

2.0 MediocreStuart, Mar 2026
HOU - STL
Read more Southwest reviews

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

It was fine. 55 minute flight. No snacks or beverage service offered. Boarding went smoothly and my walker was waiting for me on the jet way.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Everything you need to know for your flight from Chicago to Jackson

Information on your arrival and departure airports

Compare transportation modes for Chicago to Jackson

Transportation modeAverage priceAverage duration
Flights4h 13m
Trains$26415h 07m