CHI - JAN

$149 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 8/18. 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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Everything you should know

Cheapest round-trip
$297
Typical prices: $280-$436
Delta
Thu 8/20Mon 8/24
ORD - JAN • 1 stop
Cheapest one-way
$149
Typical prices: $173-$369
Delta
Tue 8/18
ORD - JAN • 1 stop
Top airlines
Cheapest • from $297 (round-trip)
Best reviews • 7.9 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 35m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 19% 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

Thu, Aug 20 - Mon, Aug 24
Delta Logo
9:54 am - 4:16 pm
ORD
-
JAN
6h 22m
1 stop
Delta Logo
5:01 pm - 11:57 pm
JAN
-
ORD
6h 56m
1 stop
$297Delta
Tue, Aug 4 - Sat, Aug 8
Delta Logo
6:05 am - 12:12 pm
MDW
-
JAN
6h 07m
1 stop
Delta Logo
10:36 am - 3:38 pm
JAN
-
MDW
5h 02m
1 stop
$297Delta
Tue, Aug 4 - Sat, Aug 8
Delta Logo
5:30 am - 12:12 pm
ORD
-
JAN
6h 42m
1 stop
Delta Logo
8:00 am - 2:48 pm
JAN
-
ORD
6h 48m
1 stop
$303Delta
Sat, Aug 1 - Sun, Aug 2
American Airlines Logo
6:48 pm - 11:48 pm
ORD
-
JAN
5h 00m
1 stop
American Airlines Logo
5:26 pm - 11:39 pm
JAN
-
ORD
6h 13m
1 stop
$345American Airlines
Sat, Aug 1 - Tue, Aug 4
American Airlines Logo
5:36 pm - 11:48 pm
ORD
-
JAN
6h 12m
1 stop
American Airlines Logo
5:26 pm - 12:43 am
JAN
-
ORD
7h 17m
1 stop
$346American Airlines
Fri, Sep 4 - Thu, Sep 10
Southwest Logo
5:25 am - 12:00 pm
MDW
-
JAN
6h 35m
1 stop
Southwest Logo
12:40 pm - 9:00 pm
JAN
-
MDW
8h 20m
2 stops
$347Southwest
Fri, Sep 4 - Thu, Sep 10
Southwest Logo
5:25 am - 12:00 pm
MDW
-
JAN
6h 35m
1 stop
Southwest Logo
12:40 pm - 8:10 pm
JAN
-
MDW
7h 30m
1 stop
$348Southwest
Fri, Sep 4 - Thu, Sep 10
Southwest Logo
12:30 pm - 8:10 pm
MDW
-
JAN
7h 40m
2 stops
Southwest Logo
12:40 pm - 9:00 pm
JAN
-
MDW
8h 20m
2 stops
$353Southwest
Fri, Sep 4 - Thu, Sep 10
American Airlines Logo
3:54 pm - 10:59 pm
ORD
-
JAN
7h 05m
1 stop
American Airlines Logo
7:06 am - 12:19 pm
JAN
-
ORD
5h 13m
1 stop
$356American Airlines
Fri, Jul 24 - Sun, Jul 26
American Airlines Logo
5:45 pm - 11:48 pm
ORD
-
JAN
6h 03m
1 stop
American Airlines Logo
5:00 am - 12:19 pm
JAN
-
ORD
7h 19m
1 stop
$397American Airlines
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 August.

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 September, where tickets cost $236 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $366 and $362 respectively.

Good to know

Low seasonJanuary
Cheapest flight$149
Best time to beat the crowds with an average 41% drop in price.
Most popular time to fly and prices are also 19% 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 5 days, the lowest price for a flight from Chicago to Jackson was $149 for a one-way ticket and $297 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?

    SkyTeam, and oneworld are the airline alliances operating flights between Chicago and Jackson, with SkyTeam 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 $541 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $436 and an overall rating of 7.8.

  • 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.
7.9
SouthwestOverall score based on 4246 reviews
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

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.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

American was having a problem with their kiosks when I arrived which made the check-in and bag drop process unusually long. Additionally, they only had one person working check-in. Eventually, the kiosks were fixed and everything else went smoothly.

The flight was short. However, my bag was delayed and was put on another flight.

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 32m
Trains$35715h 07m