JAN - CHI

$152 Find Cheap Flights from Jackson to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Jackson to Chicago departing on 8/5. 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 Chicago

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

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$263
Typical prices: $486-$420
American Airlines
Sat 9/12Tue 9/15
JAN - ORD • 1 stop
Cheapest one-way
$152
Typical prices: $233-$292
Delta
Wed 8/5
JAN - ORD • 1 stop
Top airlines
Cheapest • from $239 (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 Jackson and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $286 (round-trip)
Shortest trip • 4h 25m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 31% 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 Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Jackson to Chicago (JAN-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Jackson to Chicago 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 Jackson to Chicago

Sat, Sep 12 - Tue, Sep 15
American Airlines Logo
8:16 am - 4:00 pm
JAN
-
ORD
7h 44m
1 stop
American Airlines Logo
11:00 am - 6:50 pm
ORD
-
JAN
7h 50m
1 stop
$263American Airlines
Sat, Sep 12 - Tue, Sep 15
Delta Logo
5:35 pm - 9:46 pm
JAN
-
MDW
4h 11m
1 stop
Delta Logo
6:05 am - 12:17 pm
MDW
-
JAN
6h 12m
1 stop
$263Delta
Sat, Sep 12 - Tue, Sep 15
Southwest Logo
2:30 pm - 7:20 pm
JAN
-
MDW
4h 50m
1 stop
Southwest Logo
10:10 am - 6:05 pm
MDW
-
JAN
7h 55m
2 stops
$269Southwest
Sat, Sep 12 - Tue, Sep 15
Southwest Logo
6:00 am - 2:05 pm
JAN
-
MDW
8h 05m
2 stops
Southwest Logo
11:10 am - 7:45 pm
MDW
-
JAN
8h 35m
2 stops
$275Southwest
Wed, Jul 8 - Tue, Jul 14
American Airlines Logo
5:00 am - 11:00 am
JAN
-
ORD
6h 00m
1 stop
American Airlines Logo
1:17 pm - 9:22 pm
ORD
-
JAN
8h 05m
1 stop
$303American Airlines
Fri, Aug 21 - Mon, Aug 24
Delta Logo
3:30 pm - 8:55 pm
JAN
-
ORD
5h 25m
1 stop
Delta Logo
5:30 am - 10:37 am
ORD
-
JAN
5h 07m
1 stop
$312Delta
Fri, Aug 21 - Mon, Aug 24
Delta Logo
3:30 pm - 10:36 pm
JAN
-
MDW
7h 06m
1 stop
Delta Logo
5:10 pm - 11:11 pm
MDW
-
JAN
6h 01m
1 stop
$312Delta
Tue, Jul 28 - Thu, Aug 6
American Airlines Logo
4:24 pm - 12:01 am
JAN
-
ORD
7h 37m
1 stop
American Airlines Logo
5:05 am - 11:36 am
ORD
-
JAN
6h 31m
1 stop
$314American Airlines
Tue, Jul 28 - Thu, Aug 6
Delta Logo
5:04 pm - 10:15 pm
JAN
-
MDW
5h 11m
1 stop
Delta Logo
10:54 am - 2:45 pm
MDW
-
JAN
3h 51m
1 stop
$314Delta
Fri, Aug 21 - Mon, Aug 24
Southwest Logo
12:40 pm - 9:00 pm
JAN
-
MDW
8h 20m
2 stops
Southwest Logo
5:55 am - 12:00 pm
MDW
-
JAN
6h 05m
1 stop
$333Southwest
Booking Insights

KAYAK's insights & trends for Jackson to Chicago flights

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

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Jackson to Chicago, 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 Jackson to Chicago is September, where tickets cost $191 (return) on average. On the other hand, the most expensive months are May and June, where the average cost of round-trip tickets is $372 and $366 respectively.

Good to know

Low seasonJanuary
Cheapest flight$152
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 25% increase in price.
Flight from Jackson to Chicago O'Hare Airport

When to book flights from Jackson to Chicago

Are your dates flexible? Find out the best times to travel from Jackson to Chicago 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 Jackson to Chicago

  • What is the cheapest flight from Jackson to Chicago?

    In the last 5 days, the lowest price for a flight from Jackson to Chicago was $152 for a one-way ticket and $239 for a round-trip.

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

    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 Jackson to Chicago?

    When flying out of Jackson you will be using Jackson-Evers Intl. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

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

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

  • Which airline alliances offer flights from Jackson to Chicago?

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

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

    The two airlines most popular with KAYAK users for flights from Jackson to Chicago are Delta and Southwest. With an average price for the route of $470 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 $432 and an overall rating of 7.9.

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

    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 Jackson to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Jackson 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 Jackson to Chicago?

    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 Chicago with an airline and back to Jackson with another airline.

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

    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 Chicago from Jackson 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 Jackson to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Jackson to Chicago. 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 Jackson to Chicago? 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 4235 reviews
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

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.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

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

Information on your arrival and departure airports

Compare transportation modes for Jackson to Chicago

Transportation modeAverage priceAverage duration
Flights4h 11m
Trains$39715h 31m