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$59+ Cheap flights from Midway (MDW) to Mississippi

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAN
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Midway to Mississippi

Keep the following information in mind while searching for Midway to Mississippi flight deals. Data was last updated September 15, 2025.

Round-trip from

$207
(Southwest)

One-way from

$59
(Southwest)

Popular in

April

Cheapest in

October

Average price

$346
From Chicago Midway to Mississippi
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One-way flight from Chicago Midway to Mississippi
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Highest demand for flights based on searches. 9% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Mississippi

Cheapest flights from Midway to Mississippi
Explore the most affordable flight options available from Midway to Mississippi. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/157:45 amMDW - MEM
Nonstop1h 35mSouthwest
Mon 10/203:05 pmMEM - MDW
Nonstop1h 35mSouthwest
Deal found 9/14$207
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/185:15 amMDW - MEM
1 stop7h 55mSouthwest
Mon 10/206:55 amMEM - MDW
Nonstop1h 40mSouthwest
Deal found 9/13$227
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/178:55 pmMDW - MEM
Nonstop1h 40mSouthwest
Mon 10/203:05 pmMEM - MDW
Nonstop1h 35mSouthwest
Deal found 9/13$231
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/79:40 pmMDW - MEM
Nonstop1h 45mSouthwest
Sat 11/810:40 amMEM - MDW
1 stop11h 35mSouthwest
Deal found 9/13$247
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2512:47 pmMDW - BTR
1 stop7h 10mDelta
Wed 12/37:39 amBTR - MDW
1 stop4h 16mDelta
Deal found 9/13$249
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/231:08 pmMDW - MEM
1 stop3h 53mDelta
Fri 10/246:06 pmMEM - MDW
1 stop4h 08mDelta
Deal found 9/13$251
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2711:00 amMDW - MOB
1 stop4h 46mDelta
Tue 9/304:43 pmMOB - MDW
1 stop4h 53mDelta
Deal found 9/14$259
This Southwest deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/148:40 amMDW - JAN
1 stop6h 45mSouthwest
Sat 10/183:20 pmJAN - MDW
1 stop7h 05mSouthwest
Deal found 9/12$263
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1810:49 amMDW - BTR
1 stop7h 08mDelta
Fri 12/266:00 amBTR - MDW
1 stop5h 57mDelta
Deal found 9/13$274
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2711:00 amMDW - MOB
1 stop4h 46mDelta
Wed 10/16:00 amMOB - MDW
1 stop3h 51mDelta
Deal found 9/14$274
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/314:23 pmMDW - MOB
1 stop6h 25mDelta
Sun 11/25:43 amMOB - MDW
1 stop4h 02mDelta
Deal found 9/14$283
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/274:25 pmMDW - GPT
1 stop5h 14mDelta
Wed 10/16:08 amGPT - MDW
1 stop5h 40mDelta
Deal found 9/12$284

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Mississippi that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Mississippi that are best for you.

Fly from

Midway

Fly to

Mississippi

Route

Depart

Return

Price

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Tue 10/28

5:04 pm-10:56 pm

1 stop5h 52m

Memphis

Tue 11/4

2:07 pm-6:25 pm

1 stop4h 18m

$217

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Wed 10/15

7:45 am-9:20 am

Nonstop1h 35m

Memphis

Mon 10/20

1:55 pm-8:35 pm

1 stop6h 40m

$217

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Fri 11/7

9:40 pm-11:25 pm

Nonstop1h 45m

Memphis

Sat 11/8

7:15 am-8:50 am

Nonstop1h 35m

$231

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Fri 10/17

8:55 pm-10:35 pm

Nonstop1h 40m

Memphis

Mon 10/20

10:55 am-3:10 pm

1 stop4h 15m

$241

ChicagoBaton Rouge

MDW - BTR

MDWBTR

Chicago Midway

Tue 11/18

5:34 pm-9:52 pm

1 stop4h 18m

Baton Rouge Ryan

Mon 11/24

6:50 pm-11:32 pm

1 stop4h 42m

$249

ChicagoBaton Rouge

MDW - BTR

MDWBTR

Chicago Midway

Tue 11/25

12:47 pm-7:57 pm

1 stop7h 10m

Baton Rouge Ryan

Wed 12/3

7:39 am-11:55 am

1 stop4h 16m

$249

ChicagoBaton Rouge

MDW - BTR

MDWBTR

Chicago Midway

Wed 11/26

5:34 pm-9:52 pm

1 stop4h 18m

Baton Rouge Ryan

Wed 12/3

6:50 pm-11:32 pm

1 stop4h 42m

$249

ChicagoBaton Rouge

MDW - BTR

MDWBTR

Chicago Midway

Mon 11/17

5:34 pm-9:52 pm

1 stop4h 18m

Baton Rouge Ryan

Mon 11/24

6:50 pm-11:32 pm

1 stop4h 42m

$249

ChicagoBaton Rouge

MDW - BTR

MDWBTR

Chicago Midway

Wed 11/26

5:34 pm-9:52 pm

1 stop4h 18m

Baton Rouge Ryan

Tue 12/2

7:39 am-11:55 am

1 stop4h 16m

$249

ChicagoBaton Rouge

MDW - BTR

MDWBTR

Chicago Midway

Tue 11/25

5:34 pm-9:52 pm

1 stop4h 18m

Baton Rouge Ryan

Tue 12/2

7:39 am-11:55 am

1 stop4h 16m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 60 results
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Best time to book a flight from Midway to Mississippi

Have a flexible travel schedule? Discover the best time to fly to Mississippi from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Mississippi

What is the cheapest month to book a flight from Chicago Midway Airport to Mississippi?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Mississippi (average of $371). Flying from Chicago Midway Airport to Mississippi in March is currently the most expensive (average of $447). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Mississippi

Get insights into the airlines that provide service to Mississippi. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Mississippi. Reviews last updated September 15, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Mississippi, such as Southwest and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to Mississippi. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Mississippi?

    Departing from Chicago Midway Airport to Mississippi will take you 1h 35m. Airlines will cover a distance of 481 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Chicago Midway Airport to Mississippi?

    Most travelers choose Chicago Midway - Memphis, Chicago Midway - Baton Rouge Ryan or Chicago Midway - Jackson-Evers Intl when deciding on the best route from Chicago Midway Airport to Mississippi.

  • Can I find deals for flights from Midway to Mississippi that include hotel bookings?

    Yes. In addition to deals on Midway to Mississippi flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Mississippi?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Mississippi.

  • Can I find deals for business class flights from Midway to Mississippi?

    Yes. Cheapflights offers flight deals from Midway to Mississippi by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Mississippi?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Mississippi (average of $371). Flying from Chicago Midway Airport to Mississippi in March is currently the most expensive (average of $447). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midway to Mississippi

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Baltimore flights

Top 2 airlines flying from Midway to Mississippi

Discover the top 2 airlines that operate flights from Midway to Mississippi. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$444FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$316Average$466FlexibilityNo cancel feeOn-time63%

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