CHI - JAN

$163 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 1/8. 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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Everything you should know

Cheapest round-trip
$255
Overall average: $356
Delta
Sun 1/18Sun 1/18
ORD - JAN • 1 stop
Cheapest one-way
$163
Typical prices: $348-$410
Delta
Thu 1/8
ORD - JAN • 1 stop
Top airlines
Delta
Cheapest • from $255 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
June
Cheapest • 27% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Sun, Jan 18 - Sun, Jan 18
Delta Logo
5:30 am - 11:17 am
ORD
-
JAN
5h 47m1 stop
Delta Logo
6:59 pm - 11:59 pm
JAN
-
ORD
5h 00m1 stop
$255Delta
Sun, Jan 18 - Sun, Jan 18
Delta Logo
6:45 am - 11:17 am
MDW
-
JAN
4h 32m1 stop
Delta Logo
4:30 pm - 10:07 pm
JAN
-
MDW
5h 37m1 stop
$279Delta
Wed, Dec 31 - Thu, Jan 8
Southwest Logo
6:40 am - 5:40 pm
MDW
-
JAN
11h 00m1 stop
Southwest Logo
6:40 am - 1:30 pm
JAN
-
MDW
6h 50m1 stop
$295Southwest
Wed, Dec 31 - Thu, Jan 8
Southwest Logo
6:40 am - 5:40 pm
MDW
-
JAN
11h 00m1 stop
Southwest Logo
6:40 am - 1:10 pm
JAN
-
MDW
6h 30m2 stops
$301Southwest
Wed, Dec 31 - Thu, Jan 8
American Airlines Logo
6:07 am - 2:35 pm
ORD
-
JAN
8h 28m2 stops
American Airlines Logo
6:47 am - 2:01 pm
JAN
-
ORD
7h 14m1 stop
$304American Airlines
Fri, Jan 16 - Sun, Jan 18
Delta Logo
7:05 am - 11:17 am
ORD
-
JAN
4h 12m1 stop
Delta Logo
6:59 pm - 11:59 pm
JAN
-
ORD
5h 00m1 stop
$311Delta
Fri, Jan 16 - Sun, Jan 18
Delta Logo
6:45 am - 11:17 am
MDW
-
JAN
4h 32m1 stop
Delta Logo
4:30 pm - 10:07 pm
JAN
-
MDW
5h 37m1 stop
$311Delta
Wed, Dec 31 - Thu, Jan 8
American Airlines Logo
5:00 am - 12:48 pm
ORD
-
JAN
7h 48m1 stop
American Airlines Logo
5:30 am - 10:54 am
JAN
-
ORD
5h 24m1 stop
$313American Airlines
Tue, Feb 17 - Thu, Feb 19
Southwest Logo
10:45 am - 6:05 pm
MDW
-
JAN
7h 20m1 stop
Southwest Logo
5:35 am - 12:50 pm
JAN
-
MDW
7h 15m2 stops
$316Southwest
Fri, Feb 6 - Sun, Feb 8
American Airlines Logo
9:11 am - 4:31 pm
ORD
-
JAN
7h 20m1 stop
American Airlines Logo
12:45 pm - 7:29 pm
JAN
-
ORD
6h 44m1 stop
$367American 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 January.

What’s the cheapest day of the week to fly from Chicago to Jackson?

The average price of all round-trip flights from Chicago to Jackson clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Jackson on a Wednesday and more expensive on a Sunday. On your return trip to Chicago, you should consider flying back on a Saturday, and avoid Sundays for better deals.

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 April, where the average cost of round-trip tickets is $696 and $502 respectively.

Good to know

Low seasonNovember
Cheapest flight$163
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 12% increase in price.
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 $163 for a one-way ticket and $255 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, Delta or Southwest?

    The two airlines most popular with KAYAK users for flights from Chicago to Jackson are Delta and Southwest. With an average price for the route of $468 and an overall rating of 7.9, Delta is the most popular choice. Southwest is also a great choice for the route, with an average price of $412 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.
7.9
SouthwestOverall score based on 4253 reviews
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
Airline reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

8.0 ExcellentRussell, Dec 2025
SAN - OAK
Read more Southwest reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this 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 12m
Trains$51415h 07m