$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 7/21. 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$297
Gulfport
Gulfport1 stop$259
Memphis
Memphisnonstop$157
Jackson
Jackson1 stop$297
Gulfport
Gulfport1 stop$259
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

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
Sat, Aug 8 - Sat, Aug 22
Southwest Logo
6:15 pm - 7:55 pm
MDW
-
MEM
1h 40mnonstop
Southwest Logo
5:10 am - 6:45 am
MEM
-
MDW
1h 35mnonstop
$157Southwest
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
$158American Airlines
Sat, Aug 8 - Sat, Aug 22
Southwest Logo
2:25 pm - 7:05 pm
MDW
-
MEM
4h 40m
1 stop
Southwest Logo
12:40 pm - 2:15 pm
MEM
-
MDW
1h 35mnonstop
$167Southwest
Sat, Aug 8 - Sat, Aug 22
Southwest Logo
6:45 am - 7:05 pm
MDW
-
MEM
12h 20m
2 stops
Southwest Logo
5:10 am - 6:45 am
MEM
-
MDW
1h 35mnonstop
$172Southwest
Wed, Sep 9 - Sat, Sep 19
Delta Logo
1:55 pm - 6:49 pm
ORD
-
MEM
4h 54m
1 stop
Delta Logo
12:10 pm - 4:14 pm
MEM
-
ORD
4h 04m
1 stop
$177Delta
Sat, Sep 12 - Sat, Sep 19
Delta Logo
6:05 am - 10:47 am
MDW
-
MEM
4h 42m
1 stop
Delta Logo
10:30 am - 3:25 pm
MEM
-
MDW
4h 55m
1 stop
$177Delta
Sat, Aug 8 - Mon, Aug 10
American Airlines Logo
8:03 am - 9:54 am
ORD
-
MEM
1h 51mnonstop
American Airlines Logo
5:44 pm - 8:08 pm
MEM
-
ORD
2h 24mnonstop
$191American Airlines
Sat, Aug 8 - Mon, Aug 10
Multiple Airlines Logo
8:05 am - 7:44 am
ORD
-
MEM
23h 39m
1 stop
Multiple Airlines Logo
5:04 pm - 12:15 pm
MEM
-
ORD
19h 11m
1 stop
$214Multiple Airlines
Wed, Jul 29 - Mon, Aug 3
Multiple Airlines Logo
5:13 pm - 6:45 pm
ORD
-
GPT
25h 32m
1 stop
Multiple Airlines Logo
5:31 pm - 12:15 pm
GPT
-
ORD
18h 44m
2 stops
$259Multiple 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$79
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 12% 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 4246 reviews
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

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.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

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.

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.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

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.

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.