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$69+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — MDW
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
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 June 18, 2025.

Round-trip from

$201
(Southwest)

One-way from

$69
(Southwest)

Popular in

January

Cheapest in

May

Average price

$392
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. 5% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 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 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 June 18, 2025.

This Southwest deal was found by Cheapflights users on 6/17. 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 7/266:05 amMEM - MDW
Nonstop1h 35mSouthwest
Sun 8/38:35 amMDW - MEM
Nonstop1h 40mSouthwest
Deal found 6/17$201
This Delta deal was found by Cheapflights users on 6/17. 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 6/306:30 amMEM - MDW
1 stop5h 59mDelta
Fri 7/46:00 amMDW - MEM
1 stop7h 17mDelta
Deal found 6/17$217
This Southwest deal was found by Cheapflights users on 6/16. 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 8/112:10 pmJAN - MDW
1 stop5h 40mSouthwest
Mon 8/185:45 amMDW - JAN
1 stop5h 35mSouthwest
Deal found 6/16$217
This Delta deal was found by Cheapflights users on 6/16. 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 8/29:16 amMOB - MDW
1 stop6h 21mDelta
Sat 8/94:22 pmMDW - MOB
1 stop7h 05mDelta
Deal found 6/16$255
This Delta deal was found by Cheapflights users on 6/16. 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 9/252:40 pmJAN - MDW
1 stop7h 04mDelta
Sun 9/286:00 amMDW - JAN
1 stop5h 22mDelta
Deal found 6/16$278
This Delta deal was found by Cheapflights users on 6/16. 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 8/23:30 pmGPT - MDW
1 stop6h 12mDelta
Sat 8/94:22 pmMDW - GPT
1 stop5h 41mDelta
Deal found 6/16$289
This Delta deal was found by Cheapflights users on 6/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/155:15 pmBTR - MDW
1 stop4h 27mDelta
Tue 7/226:00 amMDW - BTR
1 stop5h 35mDelta
Deal found 6/15$294
This Mytrip deal was found by Cheapflights users on 6/17. 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.
Sun 6/298:43 pmMEM - MDW
2 stops13h 01mAllegiant Air
Fri 7/410:31 amMDW - MEM
2 stops20h 51mAllegiant Air
Deal found 6/17$355
This Mytrip deal was found by Cheapflights users on 6/17. 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 7/314:02 pmMEM - MDW
3 stops21h 54mMultiple Airlines
Sun 8/38:14 pmMDW - MEM
3 stops27h 41mMultiple Airlines
Deal found 6/17$386
This Delta deal was found by Cheapflights users on 6/17. 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 7/26:00 amGTR - MDW
1 stop5h 59mDelta
Fri 7/49:24 amMDW - GTR
2 stops10h 05mDelta
Deal found 6/17$613

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 June 18, 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

Sat 7/26

6:05 am-7:40 am

Nonstop1h 35m

Chicago Midway

Sun 8/3

8:35 am-10:15 am

Nonstop1h 40m

$201

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Mon 6/30

6:30 am-12:29 pm

1 stop5h 59m

Chicago Midway

Fri 7/4

6:00 am-1:17 pm

1 stop7h 17m

$217

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Mon 8/11

2:10 pm-7:50 pm

1 stop5h 40m

Chicago Midway

Mon 8/18

5:45 am-11:20 am

1 stop5h 35m

$217

MobileChicago

MOB - MDW

MOBMDW

Mobile

Sat 8/2

9:16 am-3:37 pm

1 stop6h 21m

Chicago Midway

Sat 8/9

4:22 pm-11:27 pm

1 stop7h 05m

$255

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 8/2

3:30 pm-9:42 pm

1 stop6h 12m

Chicago Midway

Sat 8/9

4:22 pm-10:03 pm

1 stop5h 41m

$289

Baton RougeChicago

BTR - MDW

BTRMDW

Baton Rouge Ryan

Tue 7/15

5:15 pm-9:42 pm

1 stop4h 27m

Chicago Midway

Tue 7/22

6:00 am-11:35 am

1 stop5h 35m

$294

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 7/1

2:59 pm-9:45 pm

1 stop6h 46m

Chicago Midway

Tue 7/8

6:00 am-10:05 am

1 stop4h 05m

$323

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Sun 6/29

8:43 pm-9:44 am

2 stops13h 01m

Chicago Midway

Fri 7/4

10:31 am-7:22 am

2 stops20h 51m

$355

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Thu 7/31

4:02 pm-1:56 pm

3 stops21h 54m

Chicago Midway

Sun 8/3

8:14 pm-11:55 pm

3 stops27h 41m

$386

ColumbusChicago

GTR - MDW

GTRMDW

Columbus Golden Triangle Reg.

Wed 7/2

6:00 am-11:59 am

1 stop5h 59m

Chicago Midway

Fri 7/4

9:24 am-7:29 pm

2 stops10h 05m

$613

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 21 results
1
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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 June 18, 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.

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated June 18, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Allegiant Air from Mississippi to Chicago to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

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
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

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
7,964 reviews
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

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
722 reviews
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

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
5.9
Fair
3,299 reviews
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

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 Mississippi to Midway. 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 Mississippi to Chicago Midway Airport one-way?

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $69. However, be on the lookout for offers from Delta and Frontier, as they are both options that can get you from Mississippi to Chicago Midway Airport for a low price.

  • 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 Jackson-Evers Intl - Chicago Midway or Baton Rouge Ryan - 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 Mississippi?

Book flights to Mississippi if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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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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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$424FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$338Average$396FlexibilityNo cancel feeOn-time63%

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