CHI - JAN

$154 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 4/15. 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 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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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$297
Delta
Wed 4/1Wed 4/8
ORD - JAN • 1 stop
Cheapest one-way
$154
Typical prices: $183-$359
Southwest
Wed 4/15
ORD - JAN • 2 stops
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
Nonstop flights
Not available
There are currently no direct flights between Chicago and Jackson. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Washington, D.C. (DCA)
Cheapest • Avg $349 (round-trip)
Nashville (BNA)
Shortest trip • 4h 18m (one-way)
Insights
Insights
Insights
Insights
When to travel
June
Cheapest • 29% price drop
March
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 Jackson!
Flight Deals
Booking Insights
Flight Deals

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

Wed, Apr 1 - Wed, Apr 8
Delta Logo
5:30 am - 12:07 pm
ORD
-
JAN
6h 37m
1 stop
Delta Logo
12:55 pm - 6:53 pm
JAN
-
ORD
5h 58m
1 stop
$297Delta
Wed, Apr 1 - Wed, Apr 8
Southwest Logo
2:10 pm - 8:35 pm
MDW
-
JAN
6h 25m
1 stop
Southwest Logo
1:00 pm - 4:45 pm
JAN
-
MDW
3h 45m
1 stop
$297Southwest
Wed, Apr 1 - Wed, Apr 8
Southwest Logo
6:25 am - 11:30 am
MDW
-
JAN
5h 05m
1 stop
Southwest Logo
6:30 am - 3:25 pm
JAN
-
MDW
8h 55m
2 stops
$302Southwest
Wed, Apr 1 - Wed, Apr 8
Southwest Logo
11:00 am - 8:35 pm
MDW
-
JAN
9h 35m
2 stops
Southwest Logo
6:30 am - 1:30 pm
JAN
-
MDW
7h 00m
2 stops
$307Southwest
Wed, Apr 1 - Wed, Apr 8
Southwest Logo
2:40 pm - 6:35 pm
ORD
-
JAN
3h 55m
1 stop
Southwest Logo
1:00 pm - 9:55 pm
JAN
-
ORD
8h 55m
2 stops
$312Southwest
Wed, Apr 1 - Wed, Apr 8
Southwest Logo
7:35 pm - 11:45 am
ORD
-
JAN
16h 10m
2 stops
Southwest Logo
1:00 pm - 9:55 pm
JAN
-
ORD
8h 55m
2 stops
$313Southwest
Tue, Mar 31 - Tue, Apr 7
Delta Logo
7:10 am - 12:07 pm
ORD
-
JAN
4h 57m
1 stop
Delta Logo
5:07 pm - 9:10 pm
JAN
-
ORD
4h 03m
1 stop
$317Delta
Mon, Apr 20 - Mon, Apr 27
Delta Logo
5:21 pm - 11:15 pm
MDW
-
JAN
5h 54m
1 stop
Delta Logo
5:02 pm - 10:28 pm
JAN
-
MDW
5h 26m
1 stop
$327Delta
Tue, Mar 31 - Tue, Apr 7
Southwest Logo
2:40 pm - 6:35 pm
ORD
-
JAN
3h 55m
1 stop
Southwest Logo
1:00 pm - 9:55 pm
JAN
-
ORD
8h 55m
2 stops
$327Southwest
Thu, Mar 26 - Mon, Mar 30
American Airlines Logo
6:10 am - 11:57 am
ORD
-
JAN
5h 47m
1 stop
American Airlines Logo
6:42 pm - 12:06 am
JAN
-
ORD
5h 24m
1 stop
$338American Airlines
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.

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

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

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 June, where tickets cost $323 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $756 and $577 respectively.

Good to know

Low seasonNovember
Cheapest flight$154
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 10% 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 $154 for a one-way ticket and $297 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?

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Jackson are Southwest and Delta. With an average price for the route of $401 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 $502 and an overall rating of 7.9.

  • 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 4311 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
7.0Food
8.6Crew
Airline reviews

Snacks are always pretzels. Why can't you also offer peanuts ?

6.0 GoodAnonymous, Mar 2026
STL - HOU
Read more Southwest reviews

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

Mediocre. Boarding is now unpleasant. The employees, once friendly and nice, are now regularly speaking sternly to passengers, badgering them to do things right so they can take off on time and gate check bags because they don't have enough overhead bin space. The pretzel snack was crushed flat and broken into even smaller pieces, which happens frequently lately. Drink service was suspended before they reached my row.

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The flight was flying with 30% capacity. The flight my seat from preferred seating to back of the seat. Even though i can understand that this was to balance the flight weight. The flight attendance decided to do the serving near my seat and in the middle , their noices woke me up from sleep , when i realized that the service has ended and when they were going back asked for a coffee, for which they answered they have completed teh service in my location. That really upset me as they woke me up and also rejected the coffee i asked. I ended up landing with a headache, thanks to the crew that screwed up my travel

Delayed. Hot. Passenger next to me was so large I couldn’t move.

Same experience as the flight from Norfolk to Atlanta where people are boarded in zones that don't make sense. People behind you on the plane will get on before you and they take the luggage space on your row.

The boarding process doesn't make sense since some people that will sit behind your rows are boarded before you and then they take up the luggage space above your head. I then have to wait for people to get off the plane before I can go back to get my luggage.

Good flight. Connector flight was delayed so made a short turnaround in Atlanta which was stressful. Otherwise, great crew, Staff in ATL was very informative about the delay and ensured people their connections were fine. Notified the ones that were not. Great communication.

The flight went very well, but the flight attendants didn't serve and food or drinks other than 1st class due to rough air but to be honest it wasn't that bumpy and I felt that they could've at least offered water and coffee perhaps. Also serving 1st class only is a bad look. I've been in 1st class many times and I would've felt that if the turbulence was too rough for the main cabin, it would be too rough for 1st class too.

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

My seatback screen didn’t work so that sucked because that’s what I was going to do on the plane.

Left a few minutes early. Got in 15 minutes early. Very attentive service on board. Very organized boarding.

The whole experience was excellent. As it most often is with Delta

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

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
Flights3h 55m
Trains$29615h 07m