$79 Find Cheap Flights from Chicago to Mississippi - 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 Chicago to Mississippi departing on 7/14. 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 Mississippi

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Mississippi, 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 Mississippi, as well as popular online travel agencies
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Cheap Flights from Chicago to Mississippi

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Jackson
Jackson1 stop$303
Gulfport
Gulfport1 stop$291
Memphis
Memphisnonstop$156
Jackson
Jackson1 stop$303
Gulfport
Gulfport1 stop$291
Memphis
Memphisnonstop$156

Book Cheap Chicago to Mississippi Plane Tickets

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

Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
1:28 pm - 3:17 pm
ORD
-
MEM
1h 49mnonstop
American Airlines Logo
10:28 am - 12:30 pm
MEM
-
ORD
2h 02mnonstop
$156American Airlines
Wed, Jul 15 - Tue, Jul 21
United Airlines Logo
9:20 pm - 11:21 pm
ORD
-
MEM
2h 01mnonstop
United Airlines Logo
9:46 am - 11:57 am
MEM
-
ORD
2h 11mnonstop
$157United Airlines
Wed, Jul 15 - Tue, Jul 21
Southwest Logo
9:40 pm - 11:25 pm
MDW
-
MEM
1h 45mnonstop
Southwest Logo
5:20 am - 6:55 am
MEM
-
MDW
1h 35mnonstop
$157Southwest
Wed, Jul 15 - Tue, Jul 21
Southwest Logo
12:00 pm - 5:30 pm
MDW
-
MEM
5h 30m
1 stop
Southwest Logo
5:20 am - 6:55 am
MEM
-
MDW
1h 35mnonstop
$167Southwest
Wed, Jul 15 - Tue, Jul 21
Southwest Logo
3:55 pm - 10:50 pm
MDW
-
MEM
6h 55m
2 stops
Southwest Logo
3:35 pm - 5:10 pm
MEM
-
MDW
1h 35mnonstop
$172Southwest
Tue, Jul 28 - Tue, Jul 28
Delta Logo
5:30 am - 9:27 am
ORD
-
MEM
3h 57m
1 stop
Delta Logo
1:37 pm - 6:45 pm
MEM
-
ORD
5h 08m
1 stop
$177Delta
Tue, Jul 28 - Tue, Jul 28
Delta Logo
6:00 am - 10:32 am
MDW
-
MEM
4h 32m
1 stop
Delta Logo
4:21 pm - 10:15 pm
MEM
-
MDW
5h 54m
1 stop
$177Delta
Wed, Jul 15 - Tue, Jul 21
Southwest Logo
12:00 pm - 5:30 pm
MDW
-
MEM
5h 30m
1 stop
Southwest Logo
12:25 pm - 8:40 pm
MEM
-
MDW
8h 15m
2 stops
$182Southwest
Fri, Jul 31 - Sat, Aug 8
Multiple Airlines Logo
8:05 am - 7:59 am
ORD
-
MEM
23h 54m
1 stop
Multiple Airlines Logo
9:04 am - 12:15 pm
MEM
-
ORD
27h 11m
1 stop
$232Multiple Airlines
Thu, Oct 1 - Mon, Oct 5
Multiple Airlines Logo
9:26 am - 7:05 pm
ORD
-
GPT
9h 39m
1 stop
Multiple Airlines Logo
6:46 pm - 12:02 pm
GPT
-
ORD
17h 16m
2 stops
$304Multiple Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Mississippi flights

Get data-powered insights and trends into flights from Chicago to Mississippi 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 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 Mississippi departing in July.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Mississippi, 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 Mississippi is September, when tickets cost $236 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $366 and $284 respectively.

Good to know

Low seasonJanuary
Cheapest flight$79
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Chicago Midway Airport to Memphis

FAQs - booking Mississippi flights

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

    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 Mississippi.

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

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

    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 from Chicago to Mississippi with an airline and back with another airline.

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

    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 from Chicago to Mississippi 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 Mississippi

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Mississippi. 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 Mississippi? 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 4243 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
Airline reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

2.0 MediocreIrene, Jun 2026
DEN - SFO
Read more Southwest reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

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.

Very good flight. Crew was great. No issues and we even arrived early.

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

We sat on the runway for over an hour before departure. That was unwelcome.

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

From checking to boarding, it was a seamless experience. The service agents were so helpful. The flight crew was so pleasant.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

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

Cabin class types available on flights to Mississippi

Cabin classes available on flights to Mississippi. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.