$90 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 11/6. 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

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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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$277
Gulfport
Gulfport1 stop$249
Memphis
Memphis1 stop$189
Jackson
Jackson1 stop$277
Gulfport
Gulfport1 stop$249
Memphis
Memphis1 stop$189

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

Fri, Oct 24 - Sun, Oct 26
Frontier Logo
12:11 pm - 7:27 pmMDW-MEM
7h 16m1 stop
Frontier Logo
8:10 pm - 11:16 amMEM-MDW
15h 06m1 stop
$189Frontier
Find Deal
Thu, Oct 2 - Mon, Oct 6
Frontier Logo
5:35 am - 5:48 pmORD-MEM
12h 13m1 stop
Frontier Logo
6:22 pm - 1:47 pmMEM-ORD
19h 25m2 stops
$193Frontier
Find Deal
Mon, Oct 6 - Wed, Oct 15
Multiple Airlines Logo
6:10 am - 5:27 pmORD-MEM
11h 17m1 stop
Multiple Airlines Logo
7:00 am - 9:33 pmMEM-ORD
14h 33m1 stop
$196Multiple Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 22
Southwest Logo
7:45 am - 9:20 amMDW-MEM
1h 35mnonstop
Southwest Logo
7:00 am - 8:40 amMEM-MDW
1h 40mnonstop
$197Southwest
Find Deal
Mon, Oct 6 - Tue, Oct 14
Multiple Airlines Logo
6:10 am - 5:27 pmORD-MEM
11h 17m1 stop
Multiple Airlines Logo
7:00 am - 5:53 pmMEM-ORD
10h 53m1 stop
$203Multiple Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 22
Southwest Logo
8:40 pm - 10:15 pmMDW-MEM
1h 35mnonstop
Southwest Logo
2:45 pm - 7:40 pmMEM-MDW
4h 55m1 stop
$207Southwest
Find Deal
Sat, Oct 18 - Tue, Oct 21
Delta Logo
6:45 am - 12:32 pmORD-MOB
5h 47m1 stop
Delta Logo
6:59 pm - 11:58 pmMOB-ORD
4h 59m1 stop
$211Delta
Find Deal
Tue, Oct 7 - Tue, Oct 14
Delta Logo
5:20 am - 9:28 amORD-MEM
4h 08m1 stop
Delta Logo
12:37 pm - 6:49 pmMEM-ORD
6h 12m1 stop
$217Delta
Find Deal
Tue, Oct 7 - Sat, Oct 11
American Airlines Logo
8:02 am - 9:49 amORD-MEM
1h 47mnonstop
American Airlines Logo
6:56 pm - 11:53 pmMEM-ORD
4h 57m1 stop
$224American Airlines
Find Deal
Sat, Jan 17 - Sun, Jan 18
American Airlines Logo
1:12 pm - 6:08 pmORD-BTR
4h 56m1 stop
American Airlines Logo
7:13 am - 2:15 pmBTR-ORD
7h 02m1 stop
$224American Airlines
Find Deal
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?

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 October, when tickets cost $286 (return) on average. On the other hand, the most expensive months are April and February, when the average cost of round-trip tickets is $502 and $501 respectively.

What’s the cheapest day of the week to fly from Chicago to Mississippi?

The average price of all round-trip flights from Chicago to Mississippi clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Mississippi on a Wednesday and more expensive on a Sunday. On your return trip to Chicago, you should consider flying back on a Saturday, and avoid Sundays for better deals.

Good to know

Low seasonJuly
Cheapest flight$90
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 6% 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.

  • What is the cheapest time of day to fly to Mississippi?

    The cheapest time of day to fly to Mississippi is generally in the evening, when round-trip flights cost $372 on average. Morning departures are around 6% more expensive than evening flights, on average. The most expensive time of day to fly to Mississippi is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $410.

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 4242 reviews
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

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.

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