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$55+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAN
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$124
(Frontier)

One-way from

$55
(Priceline)

Popular in

April

Cheapest in

June

Average price

$482
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. 6% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 2025.

This Frontier deal was found by Cheapflights users on 10/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/46:15 amMDW - MEM
1 stop5h 51mFrontier
Sun 12/711:56 amMEM - MDW
1 stop10h 16mFrontier
Deal found 10/30$124
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/15:47 pmMDW - MEM
1 stop15h 15mMultiple Airlines
Sun 12/78:07 pmMEM - MDW
1 stop15h 01mMultiple Airlines
Deal found 10/28$167
This Priceline deal was found by Cheapflights users on 10/28. 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 11/276:05 amMDW - MEM
1 stop8h 27mFrontier
Thu 12/41:11 pmMEM - MDW
1 stop4h 57mFrontier
Deal found 10/28$190
This Mytrip deal was found by Cheapflights users on 10/30. 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.
Thu 11/612:30 pmMDW - MEM
1 stop6h 52mFrontier
Thu 11/138:10 pmMEM - MDW
1 stop15h 20mFrontier
Deal found 10/30$199
This Frontier deal was found by Cheapflights users on 10/28. 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 11/612:30 pmMDW - MEM
1 stop6h 52mFrontier
Thu 11/203:27 pmMEM - MDW
1 stop7h 16mFrontier
Deal found 10/28$202
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/265:30 pmMDW - MEM
1 stop16h 33mMultiple Airlines
Tue 12/210:07 amMEM - MDW
2 stops22h 39mMultiple Airlines
Deal found 10/30$210
This Frontier deal was found by Cheapflights users on 10/28. 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.
Sun 11/212:30 pmMDW - MEM
1 stop7h 05mFrontier
Thu 11/203:27 pmMEM - MDW
1 stop7h 16mFrontier
Deal found 10/28$228
This Southwest deal was found by Cheapflights users on 10/28. 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 12/48:10 amMDW - MEM
Nonstop1h 45mSouthwest
Mon 12/83:00 pmMEM - MDW
Nonstop1h 35mSouthwest
Deal found 10/28$231
This Booking.com deal was found by Cheapflights users on 10/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/612:30 pmMDW - MEM
1 stop6h 52mFrontier
Sun 11/98:00 pmMEM - MDW
1 stop15h 30mFrontier
Deal found 10/30$234
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1310:12 amMDW - GPT
1 stop9h 03mMultiple Airlines
Mon 11/176:51 pmGPT - MDW
1 stop5h 39mMultiple Airlines
Deal found 10/28$241
This Delta deal was found by Cheapflights users on 10/28. 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 11/1810:47 amMDW - GPT
1 stop6h 26mDelta
Tue 11/256:03 pmGPT - MDW
1 stop5h 37mDelta
Deal found 10/28$249
This Delta deal was found by Cheapflights users on 10/28. 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 11/1112:47 pmMDW - BTR
1 stop7h 10mDelta
Sat 11/1510:34 amBTR - MDW
1 stop5h 09mDelta
Deal found 10/28$259

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 October 30, 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

Mon 12/1

5:47 pm-9:02 am

1 stop15h 15m

Memphis

Sun 12/7

5:14 pm-10:12 pm

2 stops28h 58m

$205

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Thu 12/4

10:50 am-4:05 pm

1 stop5h 15m

Memphis

Mon 12/8

3:00 pm-4:35 pm

Nonstop1h 35m

$241

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Thu 11/13

10:12 am-7:15 pm

1 stop9h 03m

Gulfport Biloxi Regional

Mon 11/17

6:51 pm-12:30 am

1 stop5h 39m

$241

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Tue 12/2

10:15 am-8:10 pm

1 stop9h 55m

Memphis

Thu 12/4

7:30 am-9:05 am

Nonstop1h 35m

$247

ChicagoBaton Rouge

MDW - BTR

MDWBTR

Chicago Midway

Fri 1/23

6:00 am-12:50 pm

1 stop6h 50m

Baton Rouge Ryan

Mon 1/26

4:02 pm-10:26 pm

1 stop6h 24m

$249

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Sat 12/13

4:29 pm-10:03 pm

1 stop5h 34m

Gulfport Biloxi Regional

Thu 12/25

5:21 pm-10:22 pm

1 stop5h 01m

$249

ChicagoGulfport

MDW - GPT

MDWGPT

Chicago Midway

Tue 11/18

10:47 am-5:13 pm

1 stop6h 26m

Gulfport Biloxi Regional

Tue 11/25

6:03 pm-11:40 pm

1 stop5h 37m

$249

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Tue 12/2

12:50 pm-6:31 pm

1 stop5h 41m

Memphis

Thu 12/4

10:32 am-4:18 pm

1 stop5h 46m

$251

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Thu 11/27

5:30 am-2:40 pm

1 stop9h 10m

Memphis

Thu 12/4

7:30 am-9:05 am

Nonstop1h 35m

$252

ChicagoBaton Rouge

MDW - BTR

MDWBTR

Chicago Midway

Tue 11/11

12:47 pm-7:57 pm

1 stop7h 10m

Baton Rouge Ryan

Sat 11/15

10:34 am-3:43 pm

1 stop5h 09m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

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
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 October 30, 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
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

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
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Crew

8.6

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 5h 15m. 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 - Jackson-Evers Intl 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

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$428FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$316Average$466FlexibilityNo cancel feeOn-time63%

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