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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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAN
Jan 13 — Jan 201
Tue 1/13
Tue 1/20
1 adult, Economy
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Cheap 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 December 14, 2025.

This Southwest deal was found by Cheapflights users on 12/12. 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.
Wed 12/318:15 amMDW - MEM
Nonstop1h 45mSouthwest
Fri 1/25:30 pmMEM - MDW
Nonstop1h 40mSouthwest
Deal found 12/12$260
This Priceline deal was found by Cheapflights users on 12/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:12 amMDW - MEM
1 stop8h 56mFrontier
Sun 12/214:18 pmMEM - MDW
1 stop5h 54mFrontier
Deal found 12/13$313
This Southwest deal was found by Cheapflights users on 12/13. 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 12/276:05 pmMDW - MEM
1 stop6h 05mSouthwest
Thu 1/17:30 amMEM - MDW
Nonstop1h 35mSouthwest
Deal found 12/13$321
This Southwest deal was found by Cheapflights users on 12/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:35 pmMDW - MEM
1 stop5h 35mSouthwest
Mon 1/54:50 pmMEM - MDW
Nonstop1h 40mSouthwest
Deal found 12/11$330
This Southwest deal was found by Cheapflights users on 12/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:35 pmMDW - MEM
1 stop5h 35mSouthwest
Sun 12/285:00 amMEM - MDW
1 stop5h 55mSouthwest
Deal found 12/11$360
This Delta deal was found by Cheapflights users on 12/12. 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.
Fri 12/125:13 pmMDW - BTR
1 stop4h 40mDelta
Sun 12/146:59 pmBTR - MDW
1 stop4h 48mDelta
Deal found 12/12$369
This Delta deal was found by Cheapflights users on 12/11. 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 12/1810:49 amMDW - AEX
1 stop5h 27mDelta
Mon 12/226:00 amAEX - MDW
1 stop5h 58mDelta
Deal found 12/11$428
This Southwest deal was found by Cheapflights users on 12/13. 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.
Thu 12/258:50 amMDW - JAN
1 stop6h 15mSouthwest
Sun 1/46:05 pmJAN - MDW
1 stop5h 00mSouthwest
Deal found 12/13$436
This Southwest deal was found by Cheapflights users on 12/13. 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.
Thu 12/258:50 amMDW - JAN
1 stop6h 15mSouthwest
Mon 1/53:05 pmJAN - MDW
1 stop6h 10mSouthwest
Deal found 12/13$456
This Southwest deal was found by Cheapflights users on 12/14. 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.
Mon 12/295:00 amMDW - JAN
1 stop6h 05mSouthwest
Sun 1/46:05 pmJAN - MDW
1 stop5h 00mSouthwest
Deal found 12/14$463
This Southwest deal was found by Cheapflights users on 12/13. 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 12/277:30 amMDW - JAN
1 stop10h 25mSouthwest
Mon 12/298:25 pmJAN - MDW
1 stop4h 45mSouthwest
Deal found 12/13$488
This Southwest deal was found by Cheapflights users on 12/12. 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.
Wed 12/248:50 amMDW - JAN
1 stop6h 15mSouthwest
Mon 12/298:25 pmJAN - MDW
1 stop4h 45mSouthwest
Deal found 12/12$491

Find flight deals from Midway to Mississippi

Keep the following information in mind while searching for Midway to Mississippi flight deals. Data was last updated December 14, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$197
(Frontier)

One-way from

$64
(Priceline)

Popular in

December

Cheapest in

June

Average price

$696
Provider with most accurate pricing for Chicago (CHI)-Jackson-Evers Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Jackson-Evers Intl flights.
Search Deals
From Chicago Midway to Mississippi
Search Deals
One-way flight from Chicago Midway to Mississippi
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 14, 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

Sat 1/17

6:45 am-12:57 pm

1 stop6h 12m

Memphis

Sun 1/18

12:14 pm-5:34 pm

1 stop5h 20m

$209

ChicagoBaton Rouge

MDW - BTR

MDWBTR

Chicago Midway

Sat 1/17

11:21 am-5:09 pm

1 stop5h 48m

Baton Rouge Ryan

Sun 1/18

10:32 am-4:29 pm

1 stop5h 57m

$209

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Sat 1/17

8:20 am-10:10 am

Nonstop1h 50m

Memphis

Mon 1/19

7:05 am-8:50 am

Nonstop1h 45m

$214

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Sat 1/17

8:20 am-10:10 am

Nonstop1h 50m

Memphis

Sun 1/18

3:05 pm-4:45 pm

Nonstop1h 40m

$219

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Tue 1/6

8:10 am-9:55 am

Nonstop1h 45m

Memphis

Sat 1/10

7:05 am-8:50 am

Nonstop1h 45m

$231

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Sat 1/17

5:31 pm-11:18 pm

1 stop5h 47m

Memphis

Mon 1/19

5:22 pm-10:22 pm

1 stop5h 00m

$234

ChicagoAlexandria

MDW - AEX

MDWAEX

Chicago Midway

Tue 1/20

6:00 am-11:04 am

1 stop5h 04m

Alexandria

Wed 1/21

5:00 pm-10:22 pm

1 stop5h 22m

$239

ChicagoAlexandria

MDW - AEX

MDWAEX

Chicago Midway

Tue 1/20

10:48 am-4:09 pm

1 stop5h 21m

Alexandria

Tue 1/27

6:12 am-11:59 am

1 stop5h 47m

$239

ChicagoAlexandria

MDW - AEX

MDWAEX

Chicago Midway

Wed 1/21

6:00 am-11:04 am

1 stop5h 04m

Alexandria

Wed 1/21

5:00 pm-10:22 pm

1 stop5h 22m

$240

ChicagoJackson

MDW - JAN

MDWJAN

Chicago Midway

Sat 1/17

5:31 pm-9:50 pm

1 stop4h 19m

Jackson-Evers Intl

Sun 1/18

12:11 pm-4:29 pm

1 stop4h 18m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/12

Showing 1-10 of 54 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
No data available for this route at this time. Please check back soon.

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 December 14, 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
7.9
Good
4,251 reviews

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,251 reviews
Southwest
7.9
Good
4,251 reviews

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,007 reviews
Southwest
7.9
Good
4,251 reviews

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 50m. 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 - Mobile 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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 December 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$424FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$316Average$486FlexibilityNo cancel feeOn-time63%

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