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$64+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAN
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$164
(Southwest)

One-way from

$64
(Southwest)

Popular in

April

Cheapest in

October

Average price

$336
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. 10% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/10. 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.
Thu 7/3110:55 pmMDW - MEM
Nonstop1h 40mSouthwest
Mon 8/45:00 amMEM - MDW
Nonstop1h 35mSouthwest
Deal found 6/10$164
This Delta deal was found by Cheapflights users on 6/11. 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 7/316:00 amMDW - MEM
1 stop5h 38mDelta
Mon 8/44:56 pmMEM - MDW
1 stop4h 46mDelta
Deal found 6/11$199
This Delta deal was found by Cheapflights users on 6/12. 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 7/56:00 amMDW - MOB
1 stop6h 11mDelta
Sat 7/126:09 amMOB - MDW
1 stop5h 49mDelta
Deal found 6/12$230
This Delta deal was found by Cheapflights users on 6/11. 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 7/264:22 pmMDW - BTR
1 stop5h 36mDelta
Sat 8/25:18 pmBTR - MDW
1 stop4h 24mDelta
Deal found 6/11$249
This Southwest deal was found by Cheapflights users on 6/10. 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.
Thu 10/25:30 amMDW - JAN
1 stop5h 50mSouthwest
Mon 10/68:05 pmJAN - MDW
1 stop4h 40mSouthwest
Deal found 6/10$257
This Delta deal was found by Cheapflights users on 6/11. 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 7/264:22 pmMDW - GPT
1 stop5h 41mDelta
Sat 8/23:30 pmGPT - MDW
1 stop6h 12mDelta
Deal found 6/11$279
This Delta deal was found by Cheapflights users on 6/10. 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 8/212:43 pmMDW - JAN
1 stop6h 50mDelta
Wed 8/65:50 amJAN - MDW
1 stop3h 55mDelta
Deal found 6/10$287
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/11:11 pmMDW - MEM
2 stops31h 02mMultiple Airlines
Sun 8/312:12 pmMEM - MDW
2 stops24h 09mMultiple Airlines
Deal found 6/11$302
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2510:31 amMDW - MEM
2 stops20h 51mAllegiant Air
Sun 7/278:42 pmMEM - MDW
2 stops12h 59mAllegiant Air
Deal found 6/11$350
This Frontier deal was found by Cheapflights users on 6/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/147:40 amMDW - MEM
2 stops11h 08mFrontier
Sun 8/177:48 pmMEM - MDW
2 stops19h 18mFrontier
Deal found 6/10$414
This Delta deal was found by Cheapflights users on 6/10. 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 7/810:30 amMDW - AEX
1 stop5h 40mDelta
Tue 7/156:09 amAEX - MDW
1 stop5h 49mDelta
Deal found 6/10$436

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 June 12, 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

Thu 7/31

10:55 pm-12:35 am

Nonstop1h 40m

Memphis

Mon 8/4

5:00 am-6:35 am

Nonstop1h 35m

$164

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Thu 7/31

6:00 am-11:38 am

1 stop5h 38m

Memphis

Mon 8/4

4:56 pm-9:42 pm

1 stop4h 46m

$199

ChicagoMobile

MDW - MOB

MDWMOB

Chicago Midway

Sat 7/5

6:00 am-12:11 pm

1 stop6h 11m

Mobile

Sat 7/12

6:09 am-11:58 am

1 stop5h 49m

$230

ChicagoBaton Rouge

MDW - BTR

MDWBTR

Chicago Midway

Sat 7/26

4:22 pm-9:58 pm

1 stop5h 36m

Baton Rouge Ryan

Sat 8/2

5:18 pm-9:42 pm

1 stop4h 24m

$249

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Thu 10/2

5:30 am-11:20 am

1 stop5h 50m

Jackson-Evers Intl

Mon 10/6

8:05 pm-12:45 am

1 stop4h 40m

$257

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 7/26

4:22 pm-10:03 pm

1 stop5h 41m

Gulfport Biloxi Regional

Sat 8/2

3:30 pm-9:42 pm

1 stop6h 12m

$279

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 8/2

12:43 pm-7:33 pm

1 stop6h 50m

Jackson-Evers Intl

Wed 8/6

5:50 am-9:45 am

1 stop3h 55m

$287

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Fri 8/1

1:11 pm-8:13 pm

2 stops31h 02m

Memphis

Sun 8/3

12:12 pm-12:21 pm

2 stops24h 09m

$302

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Fri 7/25

10:31 am-7:22 am

2 stops20h 51m

Memphis

Sun 7/27

8:42 pm-9:41 am

2 stops12h 59m

$350

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Thu 8/14

7:40 am-6:48 pm

2 stops11h 08m

Memphis

Sun 8/17

7:48 pm-3:06 pm

2 stops19h 18m

$414

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 20 results
1
2

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 $448). 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.

Rainfall in Mississippi by month

Plan your trip to Mississippi by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Mississippi ranges from 2.2 - 5.6 inches per month. December is typically the wettest month, when rainfall can reach 5.6 in. October is typically the driest time to visit Mississippi when rainfall is around 2.2 in.

Temperature in Mississippi by month

Plan your trip to Mississippi by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Mississippi, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 48.2 F).

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 June 12, 2025.
To help decide which airline to fly from Chicago to Mississippi, see what other customers have to say about Southwest, Delta and Allegiant Air. 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
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
6.0
Okay
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Mississippi one-way?

    One-way options have recently been found by users for as low as $64 on Southwest. Other airlines that offer cheap prices include Delta from $89 and Allegiant Air from $149 one-way.

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

    Most travelers choose Chicago Midway - Memphis, Chicago Midway - Jackson-Evers Intl or Chicago Midway - Baton Rouge Ryan 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 $448). 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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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$449FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$316Average$436FlexibilityNo cancel feeOn-time63%

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