$87 Find Cheap Flights from Chicago to Mississippi

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 8/5. 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$339
Gulfport
Gulfport1 stop$291
Memphis
Memphisnonstop$177
Jackson
Jackson1 stop$339
Gulfport
Gulfport1 stop$291
Memphis
Memphisnonstop$177

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, Jun 2 - Tue, Jun 9
Southwest Logo
10:05 am - 11:45 am
MDW
-
MEM
1h 40mnonstop
Southwest Logo
3:35 pm - 5:10 pm
MEM
-
MDW
1h 35mnonstop
$177Southwest
Wed, Jun 10 - Wed, Jun 17
American Airlines Logo
8:08 am - 10:02 am
ORD
-
MEM
1h 54mnonstop
American Airlines Logo
6:10 am - 8:18 am
MEM
-
ORD
2h 08mnonstop
$177American Airlines
Tue, Jun 2 - Tue, Jun 9
Southwest Logo
6:30 am - 2:20 pm
MDW
-
MEM
7h 50m
1 stop
Southwest Logo
5:20 am - 6:55 am
MEM
-
MDW
1h 35mnonstop
$187Southwest
Tue, Jun 2 - Tue, Jun 9
Frontier Logo
6:00 am - 10:59 am
MDW
-
MEM
4h 59m
1 stop
Frontier Logo
12:09 pm - 10:11 pm
MEM
-
MDW
10h 02m
1 stop
$190Frontier
Wed, Jun 10 - Wed, Jun 24
Delta Logo
5:30 am - 10:37 am
ORD
-
MEM
5h 07m
1 stop
Delta Logo
2:43 pm - 8:32 pm
MEM
-
ORD
5h 49m
1 stop
$197Delta
Tue, Jun 2 - Sat, Jun 6
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
$208United Airlines
Thu, Jun 25 - Tue, Jun 30
Frontier Logo
6:00 am - 10:55 am
MDW
-
MEM
4h 55m
1 stop
Frontier Logo
11:51 am - 10:11 pm
MEM
-
MDW
10h 20m
1 stop
$210Frontier
Wed, Jun 10 - Wed, Jun 17
American Airlines Logo
5:59 am - 11:09 am
ORD
-
MEM
5h 10m
1 stop
American Airlines Logo
6:10 am - 8:18 am
MEM
-
ORD
2h 08mnonstop
$218American Airlines
Wed, Jun 24 - Thu, Jul 9
Delta Logo
3:55 pm - 10:21 pm
ORD
-
MEM
6h 26m
1 stop
Delta Logo
6:32 am - 1:03 pm
MEM
-
ORD
6h 31m
1 stop
$228Delta
Sat, Aug 29 - Wed, Sep 2
United Airlines Logo
6:30 am - 8:00 pm
ORD
-
AEX
13h 30m
1 stop
United Airlines Logo
4:08 pm - 12:59 am
AEX
-
ORD
8h 51m
1 stop
$471United 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 February, when the average cost of round-trip tickets is $366 and $268 respectively.

Good to know

Low seasonJanuary
Cheapest flight$87
Best time to beat the crowds with an average 15% 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.
8.0
SouthwestOverall score based on 4295 reviews
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

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

2.0 MediocreAnonymous, May 2026
MCO - MDW
Read more Southwest reviews

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

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

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.

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

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.