CHI - JAN

$129 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 1/15. 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

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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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, Oct 1 - Thu, Oct 2
American Airlines Logo
3:33 pm - 10:31 pmORD-JAN
6h 58m1 stop
American Airlines Logo
6:18 pm - 11:17 pmJAN-ORD
4h 59m1 stop
$250American Airlines
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Wed, Oct 15 - Thu, Oct 16
Southwest Logo
5:15 am - 12:30 pmMDW-JAN
7h 15m1 stop
Southwest Logo
8:05 pm - 12:45 amJAN-MDW
4h 40m1 stop
$250Southwest
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Mon, Sep 29 - Tue, Sep 30
Southwest Logo
7:15 am - 6:00 pmMDW-JAN
10h 45m1 stop
Southwest Logo
1:15 pm - 5:25 pmJAN-MDW
4h 10m1 stop
$255Southwest
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Sat, Nov 8 - Mon, Nov 10
Delta Logo
4:09 pm - 10:50 pmORD-JAN
6h 41m1 stop
Delta Logo
5:59 pm - 12:01 amJAN-ORD
6h 02m1 stop
$257Delta
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Mon, Sep 29 - Tue, Sep 30
Southwest Logo
7:15 am - 6:00 pmMDW-JAN
10h 45m1 stop
Southwest Logo
1:15 pm - 8:25 pmJAN-MDW
7h 10m2 stops
$261Southwest
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Mon, Sep 29 - Tue, Sep 30
American Airlines Logo
5:08 pm - 10:43 pmORD-JAN
5h 35m1 stop
American Airlines Logo
12:04 pm - 5:18 pmJAN-ORD
5h 14m1 stop
$267American Airlines
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Thu, Jan 15 - Mon, Jan 19
Delta Logo
11:19 am - 3:56 pmORD-JAN
4h 37m1 stop
Delta Logo
6:59 pm - 11:54 pmJAN-ORD
4h 55m1 stop
$287Delta
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Sat, Nov 8 - Mon, Nov 10
Delta Logo
6:00 am - 11:18 amMDW-JAN
5h 18m1 stop
Delta Logo
7:16 pm - 11:32 pmJAN-MDW
4h 16m1 stop
$287Delta
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Fri, Nov 7 - Mon, Nov 10
United Airlines Logo
2:20 pm - 4:05 pmORD-JAN
25h 45m2 stops
United Airlines Logo
5:18 pm - 9:11 amJAN-ORD
15h 53m1 stop
$479United Airlines
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Mon, Sep 29 - Tue, Sep 30
United Airlines Logo
7:40 pm - 11:14 amORD-JAN
15h 34m2 stops
United Airlines Logo
5:05 pm - 10:10 amJAN-ORD
17h 05m1 stop
$484United Airlines
Find Deal

Everything you should know

Top airlines
American Airlines
Cheapest • from $250 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
October
Cheapest • 30% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$250
Overall average: $244
American Airlines
Wed 10/1Thu 10/2
ORD - JAN • 1 stop
Cheapest one-way
$129
Typical prices: $348-429
Delta
Thu 1/15
ORD - JAN • 1 stop
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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!
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?

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 October, where tickets cost $286 (return) on average. On the other hand, the most expensive months are April and February, where the average cost of round-trip tickets is $502 and $501 respectively.

Good to know

Low seasonFebruary
Cheapest flight$129
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly and prices are also 0% 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 $129 for a one-way ticket and $250 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, oneworld, and Star Alliance 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 $416 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 $514 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 4241 reviews
7.0Food
7.5Entertainment
8.1Boarding
8.0Comfort
8.6Crew
Airline reviews

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

10.0 ExcellentRobert, Sep 2025SFO - LAS
Read more Southwest reviews

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

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.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

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

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