$114 Find Cheap Flights from Chicago Midway Airport 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 Midway to Mississippi departing on 6/10. 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.
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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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Flights Deals

Best Mississippi Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Jackson
Jackson1 stop$257
Gulfport
Gulfport1 stop$279
Memphis
Memphisnonstop$227
Jackson
Jackson1 stop$257
Gulfport
Gulfport1 stop$279
Memphis
Memphisnonstop$227

Cheap Flight Deals from Midway to Mississippi (MDW-USMS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway 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.

Recent round-trip flight deals from Midway to Mississippi

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Mississippi.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
8:10 am - 9:50 amMDW-MEM
1h 40mnonstop
Southwest Logo
6:40 am - 8:15 amMEM-MDW
1h 35mnonstop
$227Southwest
Find Deal
Sat, May 24 - Sun, May 25
Southwest Logo
8:10 am - 9:50 amMDW-MEM
1h 40mnonstop
Southwest Logo
6:40 am - 8:15 amMEM-MDW
1h 35mnonstop
$239Southwest
Find Deal
Sat, May 24 - Sun, May 25
Southwest Logo
9:50 pm - 11:30 pmMDW-MEM
1h 40mnonstop
Southwest Logo
6:40 am - 8:15 amMEM-MDW
1h 35mnonstop
$241Southwest
Find Deal
Thu, May 22 - Sun, May 25
Southwest Logo
5:30 am - 1:40 pmMDW-MEM
8h 10m1 stop
Southwest Logo
6:40 am - 8:15 amMEM-MDW
1h 35mnonstop
$243Southwest
Find Deal
Wed, May 21 - Sun, May 25
Delta Logo
6:00 am - 11:28 amMDW-MOB
5h 28m1 stop
Delta Logo
5:55 am - 9:51 amMOB-MDW
3h 56m1 stop
$244Delta
Find Deal
Thu, Aug 14 - Sun, Aug 17
Delta Logo
10:25 am - 3:40 pmMDW-MEM
5h 15m1 stop
Delta Logo
6:37 am - 12:28 pmMEM-MDW
5h 51m1 stop
$247Delta
Find Deal
Sat, May 24 - Sun, May 25
Southwest Logo
7:00 pm - 8:40 pmMDW-MEM
1h 40mnonstop
Southwest Logo
3:10 pm - 12:05 amMEM-MDW
8h 55m1 stop
$249Southwest
Find Deal
Sun, May 25 - Thu, May 29
Delta Logo
6:00 am - 11:46 amMDW-BTR
5h 46m1 stop
Delta Logo
6:00 am - 11:59 amBTR-MDW
5h 59m1 stop
$249Delta
Find Deal
Sat, Jun 7 - Wed, Jun 11
Southwest Logo
10:55 pm - 12:35 amMDW-MEM
1h 40mnonstop
Southwest Logo
6:05 am - 7:40 amMEM-MDW
1h 35mnonstop
$253Southwest
Find Deal
Thu, Jun 5 - Sat, Jun 7
Southwest Logo
9:35 am - 11:15 amMDW-MEM
1h 40mnonstop
Southwest Logo
2:45 pm - 10:00 pmMEM-MDW
7h 15m2 stops
$254Southwest
Find Deal
Sun, May 25 - Thu, May 29
Useful Info

KAYAK's insights & trends for Midway to Mississippi flights

Get data-powered insights and trends into flights from Midway to Mississippi to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago Midway Airport to Mississippi?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport 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 Midway Airport to Mississippi is May, when tickets cost $316 (return) on average. On the other hand, the most expensive months are September and August, when the average cost of round-trip tickets is $586 and $507 respectively.

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

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

If your flying dates are flexible, you should consider flying to Mississippi on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Chicago Midway Airport to Mississippi. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.


Good to know

Low seasonAugust
High seasonNovember
Cheapest flight$114
Best time to beat the crowds but there is an average 15% increase in price.
Most popular time to fly and prices are also 22% lower on average.
Flight from Chicago Midway Airport to Memphis

FAQs - booking Mississippi flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport 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 Midway Airport to Mississippi.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Mississippi?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway Airport 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 $442 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. The most expensive time of day to fly to Mississippi is generally in the morning, which is peak travel time and where the average cost of a ticket is $442.

Top airlines flying from Midway 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 Midway 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 4294 reviews
8.2Boarding
7.1Food
8.0Comfort
7.6Entertainment
8.6Crew
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Everything you need to know for your flight from Midway to Mississippi

Information on your arrival and departure airports

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