$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 9/30. 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$281
Memphis
Memphisnonstop$157
Jackson
Jackson1 stop$303
Gulfport
Gulfport1 stop$281
Memphis
Memphisnonstop$157

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

Tue, Jul 28 - Wed, Jul 29
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
Tue, Jul 28 - Wed, Jul 29
United Airlines Logo
9:20 pm - 11:21 pm
ORD
-
MEM
2h 01mnonstop
United Airlines Logo
6:35 pm - 8:40 pm
MEM
-
ORD
2h 05mnonstop
$157United Airlines
Tue, Jul 28 - Wed, Jul 29
American Airlines Logo
10:30 pm - 12:18 am
ORD
-
MEM
1h 48mnonstop
American Airlines Logo
6:20 am - 8:29 am
MEM
-
ORD
2h 09mnonstop
$158American Airlines
Tue, Jul 28 - Wed, Jul 29
Southwest Logo
9:40 pm - 11:25 pm
MDW
-
MEM
1h 45mnonstop
Southwest Logo
4:15 pm - 9:10 pm
MEM
-
MDW
4h 55m
1 stop
$167Southwest
Wed, Jul 15 - Sat, Jul 18
United Airlines Logo
9:00 am - 11:05 am
ORD
-
MEM
2h 05mnonstop
United Airlines Logo
2:22 pm - 4:29 pm
MEM
-
ORD
2h 07mnonstop
$167United Airlines
Tue, Jul 28 - Wed, Jul 29
Southwest Logo
7:50 am - 3:00 pm
MDW
-
MEM
7h 10m
2 stops
Southwest Logo
3:35 pm - 5:10 pm
MEM
-
MDW
1h 35mnonstop
$172Southwest
Wed, Jul 15 - Tue, Jul 21
Delta Logo
5:30 am - 10:32 am
ORD
-
MEM
5h 02m
1 stop
Delta Logo
11:38 am - 6:45 pm
MEM
-
ORD
7h 07m
1 stop
$177Delta
Wed, Jul 15 - Sat, Jul 18
Southwest Logo
9:40 pm - 11:25 pm
MDW
-
MEM
1h 45mnonstop
Southwest Logo
5:30 pm - 11:45 pm
MEM
-
MDW
6h 15m
1 stop
$177Southwest
Wed, Jul 15 - Sat, Jul 18
Delta Logo
5:30 am - 9:27 am
ORD
-
MEM
3h 57m
1 stop
Delta Logo
3:54 pm - 8:33 pm
MEM
-
ORD
4h 39m
1 stop
$187Delta
Tue, Aug 4 - Tue, Aug 4
American Airlines Logo
5:07 am - 9:52 am
ORD
-
MEM
4h 45m
1 stop
American Airlines Logo
2:39 pm - 4:43 pm
MEM
-
ORD
2h 04mnonstop
$211American 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 21% drop in price.
Most popular time to fly with an average 10% 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 4235 reviews
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

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

4.0 OkaySteven, Jun 2026
ONT - LAS
Read more Southwest reviews

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.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

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.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

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.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

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.