JAN - CHI

$134 Find Cheap Flights from Jackson to Chicago

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 2/21. 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
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Everything you should know

Cheapest round-trip
$282
Overall average: $436
Delta
Wed 12/17Thu 12/25
JAN - ORD • 1 stop
Cheapest one-way
$134
Typical prices: $287-$304
American Airlines
Sat 2/21
JAN - ORD • 1 stop
Top airlines
Delta
Cheapest • from $282 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 30% price drop
June
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 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

Wed, Dec 17 - Thu, Dec 25
Delta Logo
5:48 am - 12:03 pmJAN-ORD
6h 15m1 stop
Delta Logo
6:45 am - 1:23 pmORD-JAN
6h 38m1 stop
$282Delta
Find Deal
Tue, Mar 3 - Wed, Mar 4
Delta Logo
10:40 am - 4:39 pmJAN-ORD
5h 59m1 stop
Delta Logo
7:10 am - 11:27 amORD-JAN
4h 17m1 stop
$297Delta
Find Deal
Mon, Jan 12 - Thu, Jan 15
Southwest Logo
6:10 pm - 10:55 pmJAN-MDW
4h 45m1 stop
Southwest Logo
10:45 am - 6:05 pmMDW-JAN
7h 20m1 stop
$297Southwest
Find Deal
Mon, Jan 12 - Thu, Jan 15
Southwest Logo
6:40 am - 4:30 pmJAN-MDW
9h 50m2 stops
Southwest Logo
5:55 am - 11:15 amMDW-JAN
5h 20m1 stop
$302Southwest
Find Deal
Mon, Jan 12 - Thu, Jan 15
Southwest Logo
6:40 am - 1:10 pmJAN-MDW
6h 30m2 stops
Southwest Logo
8:15 am - 3:40 pmMDW-JAN
7h 25m2 stops
$307Southwest
Find Deal
Tue, Dec 9 - Fri, Dec 12
Delta Logo
12:17 pm - 6:43 pmJAN-ORD
6h 26m1 stop
Delta Logo
11:15 am - 5:21 pmORD-JAN
6h 06m1 stop
$322Delta
Find Deal
Thu, Nov 20 - Mon, Nov 24
American Airlines Logo
6:41 am - 1:11 pmJAN-ORD
6h 30m1 stop
American Airlines Logo
5:00 am - 1:20 pmORD-JAN
8h 20m1 stop
$387American Airlines
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Wed, Dec 17 - Sun, Dec 21
American Airlines Logo
1:46 pm - 7:22 pmJAN-ORD
5h 36m1 stop
American Airlines Logo
1:27 pm - 9:45 pmORD-JAN
8h 18m1 stop
$428American Airlines
Find Deal
Thu, Jan 1 - Sun, Jan 4
United Airlines Logo
2:03 pm - 12:14 amJAN-ORD
10h 11m1 stop
United Airlines Logo
7:42 pm - 7:42 pmORD-JAN
24h 00m2 stops
$539United Airlines
Find Deal
Tue, Dec 9 - Fri, Dec 12
United Airlines Logo
12:05 pm - 11:32 pmJAN-ORD
11h 27m2 stops
United Airlines Logo
4:45 pm - 9:56 pmORD-JAN
5h 11m1 stop
$557United Airlines
Find Deal
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.

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

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

If your flying dates are flexible, you should consider flying to Chicago on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Jackson to Chicago. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.

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 $301 (return) on average. On the other hand, the most expensive months are January and April, where the average cost of round-trip tickets is $581 and $562 respectively.

Good to know

Low seasonFebruary
Cheapest flight$134
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 9% lower on average.
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 3 days, the lowest price for a flight from Jackson to Chicago was $134 for a one-way ticket and $282 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?

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

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

    The two airlines most popular with KAYAK users for flights from Jackson to Chicago are Southwest and Delta. With an average price for the route of $386 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 $455 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.
8.0
SouthwestOverall score based on 4241 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

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

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

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 06m
Trains$43615h 31m

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