$89 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 7/7. 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 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Mississippi

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Jackson
Jackson1 stop$287
Gulfport
Gulfport1 stop$281
Memphis
Memphisnonstop$240
Jackson
Jackson1 stop$287
Gulfport
Gulfport1 stop$281
Memphis
Memphisnonstop$240

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, Nov 3 - Thu, Nov 5
Southwest Logo
8:45 pm - 10:30 pm
MDW
-
MEM
1h 45mnonstop
Southwest Logo
4:15 pm - 8:50 pm
MEM
-
MDW
4h 35m
1 stop
$240Southwest
Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
4:53 pm - 10:50 pm
ORD
-
MEM
5h 57m
1 stop
American Airlines Logo
6:32 am - 8:45 am
MEM
-
ORD
2h 13mnonstop
$241American Airlines
Tue, Aug 4 - Mon, Aug 10
Southwest Logo
8:45 pm - 10:25 pm
MDW
-
MEM
1h 40mnonstop
Southwest Logo
4:55 pm - 11:20 pm
MEM
-
MDW
6h 25m
1 stop
$241Southwest
Wed, Jul 22 - Wed, Jul 29
Frontier Logo
5:13 pm - 6:25 pm
ORD
-
MEM
25h 12m
1 stop
Frontier Logo
7:48 pm - 8:52 pm
MEM
-
ORD
25h 04m
1 stop
$242Frontier
Tue, Jul 28 - Wed, Jul 29
United Airlines Logo
9:20 pm - 11:21 pm
ORD
-
MEM
2h 01mnonstop
United Airlines Logo
7:25 am - 9:30 am
MEM
-
ORD
2h 05mnonstop
$243United Airlines
Thu, Aug 13 - Mon, Aug 24
American Airlines Logo
9:20 pm - 11:16 pm
ORD
-
MEM
1h 56mnonstop
American Airlines Logo
3:59 pm - 6:10 pm
MEM
-
ORD
2h 11mnonstop
$245American Airlines
Thu, Aug 13 - Mon, Aug 24
Southwest Logo
8:45 pm - 10:25 pm
MDW
-
MEM
1h 40mnonstop
Southwest Logo
5:15 am - 6:50 am
MEM
-
MDW
1h 35mnonstop
$245Southwest
Tue, Nov 3 - Thu, Nov 5
Delta Logo
11:30 am - 4:54 pm
ORD
-
MEM
5h 24m
1 stop
Delta Logo
6:10 am - 12:37 pm
MEM
-
ORD
6h 27m
1 stop
$250Delta
Thu, Aug 6 - Mon, Aug 10
Delta Logo
6:05 am - 12:43 pm
MDW
-
MEM
6h 38m
1 stop
Delta Logo
5:00 pm - 10:36 pm
MEM
-
MDW
5h 36m
1 stop
$251Delta
Tue, Oct 27 - Wed, Oct 28
United Airlines Logo
8:10 pm - 9:53 pm
ORD
-
MEM
1h 43mnonstop
United Airlines Logo
7:30 am - 9:25 am
MEM
-
ORD
1h 55mnonstop
$261United 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 August.

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$89
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Chicago O'Hare 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
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
8.6Crew
Airline reviews

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!

10.0 ExcellentAnonymous, Jun 2026
OKC - LAS
Read more Southwest reviews

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

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

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

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

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

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

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.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

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.