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

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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Mississippi to Midway

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

Round-trip from

$193
(Southwest)

One-way from

$59
(Southwest)

Popular in

January

Cheapest in

September

Average price

$301
From Mississippi to Chicago Midway
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One-way flight from Mississippi to Chicago Midway
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Highest demand for flights based on searches. 7% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 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 Mississippi to Midway

Cheapest flights from Mississippi to Midway
Explore the most affordable flight options available from Mississippi to Midway. 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 9/12. 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.
Thu 11/64:50 pmMEM - MDW
Nonstop1h 40mSouthwest
Mon 11/105:05 amMDW - MEM
1 stop6h 45mSouthwest
Deal found 9/12$193
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.
Wed 10/11:50 pmMEM - MDW
Nonstop1h 40mSouthwest
Fri 10/38:55 pmMDW - MEM
Nonstop1h 40mSouthwest
Deal found 9/12$194
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.
Wed 10/153:20 pmMEM - MDW
Nonstop1h 35mSouthwest
Wed 10/227:45 amMDW - MEM
Nonstop1h 35mSouthwest
Deal found 9/13$197
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/68:10 pmMEM - MDW
2 stops18h 12mFrontier
Mon 11/1012:30 pmMDW - MEM
1 stop6h 52mFrontier
Deal found 9/12$203
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.
Mon 10/276:55 amMEM - MDW
Nonstop1h 40mSouthwest
Wed 11/58:40 pmMDW - MEM
Nonstop1h 45mSouthwest
Deal found 9/14$207
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 11/15:43 amMOB - MDW
1 stop4h 02mDelta
Sat 11/84:23 pmMDW - MOB
1 stop6h 25mDelta
Deal found 9/14$211
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/166:48 pmMEM - MDW
1 stop16h 28mMultiple Airlines
Mon 10/205:28 pmMDW - MEM
1 stop26h 17mMultiple Airlines
Deal found 9/15$214
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.
Mon 12/86:03 pmJAN - MDW
1 stop5h 29mDelta
Tue 12/96:00 amMDW - JAN
1 stop4h 13mDelta
Deal found 9/13$217
This Southwest deal was found by Cheapflights users on 9/15. 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 10/273:05 pmMEM - MDW
Nonstop1h 35mSouthwest
Wed 10/297:55 amMDW - MEM
1 stop6h 40mSouthwest
Deal found 9/15$217
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/318:09 pmMEM - MDW
1 stop14h 17mMultiple Airlines
Mon 11/312:30 pmMDW - MEM
1 stop6h 52mMultiple Airlines
Deal found 9/14$218
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 11/186:50 pmBTR - MDW
1 stop4h 42mDelta
Mon 11/245:34 pmMDW - BTR
1 stop4h 18mDelta
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.
Sat 9/274:39 pmBTR - MDW
1 stop4h 31mDelta
Sat 10/44:25 pmMDW - BTR
1 stop5h 47mDelta
Deal found 9/13$254

Cheapflights Fare Finder

 
Customize your flight search to find flights from Mississippi to Midway 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 Mississippi to Chicago Midway Airport that are best for you.

Fly from

Mississippi

Fly to

Midway

Route

Depart

Return

Price

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Wed 10/15

3:20 pm-4:55 pm

Nonstop1h 35m

Chicago Midway

Wed 10/22

7:45 am-9:20 am

Nonstop1h 35m

$197

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Thu 11/6

2:20 pm-11:00 pm

2 stops8h 40m

Chicago Midway

Mon 11/10

8:00 am-9:45 am

Nonstop1h 45m

$198

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Wed 10/1

1:50 pm-3:30 pm

Nonstop1h 40m

Chicago Midway

Fri 10/3

6:25 pm-12:10 am

1 stop5h 45m

$204

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Mon 10/20

6:55 am-8:35 am

Nonstop1h 40m

Chicago Midway

Tue 10/21

7:45 am-9:20 am

Nonstop1h 35m

$207

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Wed 12/17

7:30 am-9:05 am

Nonstop1h 35m

Chicago Midway

Mon 12/22

10:20 pm-12:05 am

Nonstop1h 45m

$207

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Mon 10/27

6:55 am-8:35 am

Nonstop1h 40m

Chicago Midway

Wed 10/29

8:40 pm-10:15 pm

Nonstop1h 35m

$207

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Mon 10/27

6:55 am-8:35 am

Nonstop1h 40m

Chicago Midway

Tue 10/28

8:40 pm-10:15 pm

Nonstop1h 35m

$207

MobileChicago

MOB - MDW

MOBMDW

Mobile

Sat 11/1

5:43 am-9:45 am

1 stop4h 02m

Chicago Midway

Sat 11/8

4:23 pm-10:48 pm

1 stop6h 25m

$211

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Tue 10/28

2:07 pm-6:25 pm

1 stop4h 18m

Chicago Midway

Wed 11/5

5:09 pm-10:56 pm

1 stop5h 47m

$217

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Wed 10/29

10:40 am-4:09 pm

1 stop5h 29m

Chicago Midway

Tue 11/4

10:40 am-5:01 pm

1 stop6h 21m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 55 results
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Best time to book a flight from Mississippi to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Mississippi 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 Mississippi to Chicago Midway Airport

What is the cheapest time of day to fly from MS to MDW?

Find hourly flight availability from Mississippi to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Mississippi to Chicago Midway Airport as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Mississippi to Midway. 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 Mississippi to Chicago Midway Airport?

    Departing from Mississippi to Chicago Midway Airport will take you 1h 35m. There are 481 mi between Mississippi and Chicago Midway Airport. This flight may include one or multiple stops.

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

    The most popular route from Mississippi to Chicago Midway Airport is Memphis - Chicago Midway. You may also consider Baton Rouge Ryan - Chicago Midway or Jackson-Evers Intl - Chicago Midway.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Mississippi to Midway 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 Mississippi to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Mississippi to Chicago Midway Airport (average of $160). Flying from Mississippi to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Mississippi to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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John F Kennedy Intl to Midway flights
Ontario to O'Hare Intl flights
LaGuardia to Midway flights
Newark to Midway flights
Atlanta to Midway flights
Los Angeles to Midway flights
Santa Ana to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Austin to O'Hare Intl flights
Dulles Intl to Midway flights
Baltimore to Midway flights
Hobby to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Philadelphia to Midway flights
Charlotte to O'Hare Intl flights
Minneapolis to Midway flights
Minneapolis to O'Hare Intl flights
Portland to O'Hare Intl flights
San Diego to O'Hare Intl flights
Tampa to O'Hare Intl flights
Love Field to O'Hare Intl flights
San Francisco to Midway flights
Burbank to O'Hare Intl flights
Miami to O'Hare Intl flights
Hartford to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Orlando to O'Hare Intl flights
San Jose to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Hobby to Midway flights
Love Field to Midway flights
Denver to Midway flights
Seattle to Midway flights
Providence to O'Hare Intl flights
Reagan-National to Midway flights

Top 2 airlines flying from Mississippi to Midway

Discover the top 2 airlines that operate flights from Mississippi to Midway. 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$116Average$382FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$234Average$392FlexibilityNo cancel feeOn-time63%

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