CHI - JAN

$119 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 8/9. 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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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 28 - Thu, Sep 4
Delta Logo
5:45 am - 12:24 pmORD-JAN
6h 39m1 stop
Delta Logo
10:55 am - 4:28 pmJAN-ORD
5h 33m1 stop
$237Delta
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Sat, Aug 9 - Mon, Aug 11
Delta Logo
6:00 am - 10:04 amMDW-JAN
4h 04m1 stop
Delta Logo
3:01 pm - 9:44 pmJAN-MDW
6h 43m1 stop
$237Delta
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Wed, Aug 13 - Wed, Aug 20
Southwest Logo
10:30 am - 6:10 pmMDW-JAN
7h 40m2 stops
Southwest Logo
6:50 pm - 11:20 pmJAN-MDW
4h 30m1 stop
$242Southwest
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Wed, Aug 13 - Wed, Aug 20
Southwest Logo
12:50 pm - 8:05 pmMDW-JAN
7h 15m2 stops
Southwest Logo
1:15 pm - 8:25 pmJAN-MDW
7h 10m2 stops
$247Southwest
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Fri, Aug 15 - Tue, Aug 19
Delta Logo
5:45 am - 12:24 pmORD-JAN
6h 39m1 stop
Delta Logo
11:31 am - 4:28 pmJAN-ORD
4h 57m1 stop
$259Delta
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Sat, Sep 13 - Sun, Sep 14
Delta Logo
6:00 am - 11:38 amMDW-JAN
5h 38m1 stop
Delta Logo
5:50 am - 9:40 amJAN-MDW
3h 50m1 stop
$259Delta
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Fri, Aug 8 - Sun, Aug 10
American Airlines Logo
12:36 pm - 8:19 pmORD-JAN
7h 43m1 stop
American Airlines Logo
5:10 am - 10:43 amJAN-ORD
5h 33m1 stop
$281American Airlines
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Mon, Aug 11 - Mon, Aug 18
United Airlines Logo
9:20 pm - 1:29 pmORD-JAN
16h 09m2 stops
United Airlines Logo
2:07 pm - 11:47 pmJAN-ORD
9h 40m1 stop
$383United Airlines
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Mon, Oct 13 - Fri, Oct 17
American Airlines Logo
5:22 am - 10:36 amORD-JAN
5h 14m1 stop
American Airlines Logo
6:15 pm - 11:13 pmJAN-ORD
4h 58m1 stop
$390American Airlines
Find Deal
Sat, Aug 9 - Mon, Aug 11
United Airlines Logo
7:00 am - 9:59 pmORD-JAN
14h 59m2 stops
United Airlines Logo
7:00 am - 12:15 amJAN-ORD
17h 15m1 stop
$418United Airlines
Find Deal
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.

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
High seasonMarch
Cheapest flight$119
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly with an average 21% 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 $119 for a one-way ticket and $237 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, 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 $526 and an overall rating of 8.0, Delta is the most popular choice. Southwest is also a great choice for the route, with an average price of $416 and an overall rating of 8.0.

  • 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 4239 reviews
7.6Entertainment
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
Airline reviews

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

4.0 OkayBobby, Jul 2025BNA - MDW
Read more Southwest reviews

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

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

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Food was surprisingly good but the WiFi was not great

this crew didn't care much. bumping carts into seats more times than i care to remember

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

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.

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 meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

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 04m
Trains$38715h 07m

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