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$100+ 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAN
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$224
(Delta)

One-way from

$100
(Delta)

Popular in

April

Cheapest in

October

Average price

$416
Provider with most accurate pricing for Chicago (CHI)-Jackson-Evers Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Jackson-Evers Intl flights.
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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. 13% potential increase in price ($62 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 May 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 May 1, 2025.

This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 5/286:00 amMDW - BTR
1 stop7h 08mDelta
Wed 6/46:00 amBTR - MDW
1 stop5h 53mDelta
Deal found 4/30$224
This Southwest deal was found by Cheapflights users on 4/30. 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 5/248:10 amMDW - MEM
Nonstop1h 40mSouthwest
Sun 5/256:40 amMEM - MDW
Nonstop1h 35mSouthwest
Deal found 4/30$239
This Delta deal was found by Cheapflights users on 4/29. 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 8/146:00 amMDW - MOB
1 stop5h 28mDelta
Sun 8/175:55 amMOB - MDW
1 stop3h 56mDelta
Deal found 4/29$244
This Delta deal was found by Cheapflights users on 4/30. 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 5/2410:25 amMDW - MEM
1 stop5h 15mDelta
Sun 5/256:37 amMEM - MDW
1 stop5h 51mDelta
Deal found 4/30$247
This Delta deal was found by Cheapflights users on 4/30. 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 5/244:15 pmMDW - GPT
1 stop5h 21mDelta
Sat 5/315:03 pmGPT - MDW
1 stop4h 10mDelta
Deal found 4/30$254
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 5/286:00 amMDW - JAN
1 stop4h 19mDelta
Wed 6/47:40 amJAN - MDW
1 stop4h 13mDelta
Deal found 4/30$257
This Southwest deal was found by Cheapflights users on 4/30. 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 5/288:15 amMDW - JAN
1 stop5h 35mSouthwest
Wed 6/412:55 pmJAN - MDW
2 stops6h 15mSouthwest
Deal found 4/30$262
This Mytrip deal was found by Cheapflights users on 4/30. 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 6/68:36 pmMDW - MEM
2 stops19h 43mMultiple Airlines
Sun 6/88:15 amMEM - MDW
2 stops35h 31mMultiple Airlines
Deal found 4/30$332
This Delta deal was found by Cheapflights users on 4/30. 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 6/1410:26 amMDW - AEX
1 stop5h 45mDelta
Sat 6/216:09 amAEX - MDW
1 stop5h 50mDelta
Deal found 4/30$346

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 May 1, 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

ChicagoBaton Rouge

MDW - BTR

MDWBTR

Chicago Midway

Wed 5/28

6:00 am-1:08 pm

1 stop7h 08m

Baton Rouge Ryan

Wed 6/4

6:00 am-11:53 am

1 stop5h 53m

$224

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Sat 5/24

8:10 am-9:50 am

Nonstop1h 40m

Memphis

Sun 5/25

6:40 am-8:15 am

Nonstop1h 35m

$239

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Sat 5/24

10:25 am-3:40 pm

1 stop5h 15m

Memphis

Sun 5/25

6:37 am-12:28 pm

1 stop5h 51m

$247

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 5/24

4:15 pm-9:36 pm

1 stop5h 21m

Gulfport Biloxi Regional

Sat 5/31

5:03 pm-9:13 pm

1 stop4h 10m

$254

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Wed 5/28

6:00 am-10:19 am

1 stop4h 19m

Jackson-Evers Intl

Wed 6/4

7:40 am-11:53 am

1 stop4h 13m

$257

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Wed 5/28

8:15 am-1:50 pm

1 stop5h 35m

Jackson-Evers Intl

Wed 6/4

12:55 pm-7:10 pm

2 stops6h 15m

$262

ChicagoMobile

MDW - MOB

MDWMOB

Chicago Midway

Tue 7/29

6:00 am-12:00 pm

1 stop6h 00m

Mobile

Sun 8/3

12:45 pm-6:02 pm

1 stop5h 17m

$280

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Fri 6/6

8:36 pm-4:19 pm

2 stops19h 43m

Memphis

Sun 6/8

8:15 am-7:46 pm

2 stops35h 31m

$332

ChicagoAlexandria

MDW - AEX

MDWAEX

Chicago Midway

Sat 6/14

10:26 am-4:11 pm

1 stop5h 45m

Alexandria

Sat 6/21

6:09 am-11:59 am

1 stop5h 50m

$346

ChicagoBaton Rouge

MDW - BTR

MDWBTR

Chicago Midway

Sat 5/24

10:25 am-3:52 pm

1 stop5h 27m

$100

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 18 results
1
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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 $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 May 1, 2025.
To help decide which airline to fly from Chicago to Mississippi, see what other customers have to say about Southwest, Delta and Frontier. 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
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $100 on Delta. Other airlines that offer cheap prices include Frontier from $106 and Southwest from $114 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$253Average$464FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$316Average$436FlexibilityNo cancel feeOn-time63%

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