JAN - CHI

$184 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 4/7. 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
$297
Overall average: $492
Delta
Tue 5/5Tue 5/12
JAN - ORD • 1 stop
Cheapest one-way
$149
Typical prices: $143-$263
American Airlines
Tue 4/7
JAN - ORD • 1 stop
Top airlines
Delta
Cheapest • from $297 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 29% 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

Tue, May 5 - Tue, May 12
Delta Logo
10:59 am - 4:42 pm
JAN
-
ORD
5h 43m
1 stop
Delta Logo
6:00 am - 10:02 am
ORD
-
JAN
4h 02m
1 stop
$297Delta
Sat, Apr 18 - Wed, Apr 29
Delta Logo
5:02 pm - 11:59 pm
JAN
-
ORD
6h 57m
1 stop
Delta Logo
5:10 am - 10:13 am
ORD
-
JAN
5h 03m
1 stop
$309Delta
Sat, Feb 28 - Sat, Mar 7
Delta Logo
4:58 pm - 10:31 pm
JAN
-
MDW
5h 33m
1 stop
Delta Logo
4:13 pm - 11:07 pm
MDW
-
JAN
6h 54m
1 stop
$309Delta
Sat, Apr 11 - Mon, Apr 13
Delta Logo
2:47 pm - 8:02 pm
JAN
-
ORD
5h 15m
1 stop
Delta Logo
11:19 am - 4:15 pm
ORD
-
JAN
4h 56m
1 stop
$321Delta
Sat, Apr 11 - Mon, Apr 13
Delta Logo
5:35 am - 9:56 am
JAN
-
MDW
4h 21m
1 stop
Delta Logo
5:21 pm - 11:15 pm
MDW
-
JAN
5h 54m
1 stop
$321Delta
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
12:25 pm - 9:50 pm
JAN
-
ORD
9h 25m
2 stops
Southwest Logo
2:40 pm - 7:35 pm
ORD
-
JAN
4h 55m
1 stop
$326Southwest
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
6:05 am - 1:15 pm
JAN
-
MDW
7h 10m
1 stop
Southwest Logo
12:35 pm - 9:50 pm
MDW
-
JAN
9h 15m
2 stops
$326Southwest
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
6:05 am - 5:05 pm
JAN
-
MDW
11h 00m
2 stops
Southwest Logo
11:45 am - 9:50 pm
MDW
-
JAN
10h 05m
2 stops
$331Southwest
Tue, May 5 - Tue, May 12
Delta Logo
5:36 am - 9:56 am
JAN
-
MDW
4h 20m
1 stop
Delta Logo
6:00 am - 11:20 am
MDW
-
JAN
5h 20m
1 stop
$332Delta
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
12:25 pm - 9:50 pm
JAN
-
ORD
9h 25m
2 stops
Southwest Logo
6:00 am - 9:50 pm
ORD
-
JAN
15h 50m
2 stops
$337Southwest
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 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 April and July, where the average cost of round-trip tickets is $595 and $556 respectively.

Good to know

Low seasonFebruary
Cheapest flight$149
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 8% 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 $184 for a one-way ticket and $297 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 $414 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 4267 reviews
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

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.

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

Information on your arrival and departure airports