JAN - CHI

$150 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 8/25. 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

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Everything you should know

Cheapest round-trip
$309
Typical prices: $236-$539
Delta
Thu 8/20Sat 8/22
JAN - MDW • 1 stop
Cheapest one-way
$150
Typical prices: $151-$263
Delta
Tue 8/25
JAN - ORD • 1 stop
Top airlines
Cheapest • from $309 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
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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 $331 (round-trip)
Shortest trip • 4h 10m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 26% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Thu, Aug 20 - Sat, Aug 22
Delta Logo
7:49 am - 11:51 am
JAN
-
MDW
4h 02m
1 stop
Delta Logo
10:56 am - 4:16 pm
MDW
-
JAN
5h 20m
1 stop
$309Delta
Wed, Sep 9 - Thu, Sep 17
Delta Logo
11:08 am - 3:24 pm
JAN
-
MDW
4h 16m
1 stop
Delta Logo
6:05 am - 10:23 am
MDW
-
JAN
4h 18m
1 stop
$309Delta
Wed, Nov 18 - Mon, Nov 23
American Airlines Logo
7:00 am - 2:12 pm
JAN
-
ORD
7h 12m
1 stop
American Airlines Logo
6:00 am - 11:44 am
ORD
-
JAN
5h 44m
1 stop
$309American Airlines
Wed, Oct 28 - Sat, Oct 31
American Airlines Logo
4:46 pm - 11:59 pm
JAN
-
ORD
7h 13m
1 stop
American Airlines Logo
4:53 pm - 10:55 pm
ORD
-
JAN
6h 02m
1 stop
$309American Airlines
Thu, Sep 10 - Sat, Sep 12
Southwest Logo
12:40 pm - 4:55 pm
JAN
-
MDW
4h 15m
1 stop
Southwest Logo
1:45 pm - 7:10 pm
MDW
-
JAN
5h 25m
1 stop
$309Southwest
Wed, Sep 9 - Thu, Sep 10
Southwest Logo
1:30 pm - 4:55 pm
JAN
-
MDW
3h 25m
1 stop
Southwest Logo
5:25 am - 12:00 pm
MDW
-
JAN
6h 35m
1 stop
$309Southwest
Mon, Sep 7 - Sat, Sep 19
Delta Logo
5:01 pm - 10:36 pm
JAN
-
MDW
5h 35m
1 stop
Delta Logo
4:30 pm - 9:34 pm
MDW
-
JAN
5h 04m
1 stop
$309Delta
Mon, Aug 24 - Mon, Aug 31
American Airlines Logo
5:28 pm - 11:30 pm
JAN
-
ORD
6h 02m
1 stop
American Airlines Logo
4:53 pm - 10:39 pm
ORD
-
JAN
5h 46m
1 stop
$309American Airlines
Sat, Oct 31 - Tue, Nov 3
United Airlines Logo
1:57 pm - 11:26 pm
JAN
-
ORD
9h 29m
1 stop
United Airlines Logo
7:30 am - 9:18 pm
ORD
-
JAN
13h 48m
1 stop
$439United Airlines
Sat, Oct 31 - Tue, Nov 3
United Airlines Logo
9:00 am - 8:19 pm
JAN
-
ORD
11h 19m
2 stops
United Airlines Logo
9:15 am - 9:18 pm
ORD
-
JAN
12h 03m
1 stop
$464United Airlines
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 October, where tickets cost $331 (return) on average. On the other hand, the most expensive months are June and March, where the average cost of round-trip tickets is $674 and $565 respectively.

Good to know

Low season

January

Cheapest flight

$150
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly with an average 14% 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 $150 for a one-way ticket and $309 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, 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 $439 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 $456 and an overall rating of 7.8.

  • 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 4227 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
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.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

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

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

It was as good as it could be. Flying is not a pleasant experience these days.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

Got on the plane and sat there for an hour before departure.

Cramped seating for me. Luckily it wasn’t a long flight

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

long flights are never truly comfortable but the airline did their best. crew was great and the flight was safe.

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

The staff did not do a good job of getting everyone boarded quickly, so we missed our take off window and had to sit on the tarmac for 20+ min waiting for our turn. The plan was old. Pockets on the back of seats were torn and tearing off. One of the attendants was rude-she would ask a question but he walking away before you finished answering so she kept getting our drink orders wrong.

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

Nothing, I wont be flying American Airlines again and will not be recommending anyone to fly American Airlines. It was the worst experience flying I've ever had.

My luggage was not sent with us. Not sure if this is Envoy Air responsibility but that was a very BAD experience

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

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 15m
Trains$29215h 31m