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Midway

$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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — MDW
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$203
(Southwest)

One-way from

$69
(Southwest)

Popular in

January

Cheapest in

May

Average price

$464
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. 4% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Southwest deal was found by Cheapflights users on 7/1. 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 8/143:35 pmMEM - MDW
1 stop6h 25mSouthwest
Sun 8/179:00 amMDW - MEM
1 stop4h 20mSouthwest
Deal found 7/1$203
This Delta deal was found by Cheapflights users on 7/1. 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 7/2912:06 pmMEM - MDW
1 stop5h 33mDelta
Tue 8/59:25 amMDW - MEM
1 stop3h 58mDelta
Deal found 7/1$214
This Delta deal was found by Cheapflights users on 6/30. 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.
Tue 8/127:43 amJAN - MDW
1 stop4h 05mDelta
Tue 8/196:04 amMDW - JAN
1 stop4h 42mDelta
Deal found 6/30$237
This Delta deal was found by Cheapflights users on 7/2. 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 8/164:31 pmMOB - MDW
1 stop4h 41mDelta
Sat 8/236:04 amMDW - MOB
1 stop5h 23mDelta
Deal found 7/2$245
This Delta deal was found by Cheapflights users on 7/2. 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 8/216:00 amBTR - MDW
1 stop5h 48mDelta
Fri 8/296:00 amMDW - BTR
1 stop5h 00mDelta
Deal found 7/2$249
This Delta deal was found by Cheapflights users on 7/2. 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 8/233:45 pmGPT - MDW
1 stop5h 27mDelta
Tue 8/264:25 pmMDW - GPT
1 stop5h 13mDelta
Deal found 7/2$249
This Southwest deal was found by Cheapflights users on 7/3. 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 8/207:05 amJAN - MDW
2 stops7h 20mSouthwest
Sun 8/247:10 amMDW - JAN
1 stop7h 15mSouthwest
Deal found 7/3$277
This Mytrip deal was found by Cheapflights users on 7/2. 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 7/2712:12 pmMEM - MDW
2 stops21h 29mAllegiant Air
Fri 8/11:11 pmMDW - MEM
2 stops18h 11mAllegiant Air
Deal found 7/2$310
This Delta deal was found by Cheapflights users on 7/2. 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 7/52:34 pmGTR - MDW
1 stop7h 11mDelta
Sat 7/124:22 pmMDW - GTR
1 stop5h 13mDelta
Deal found 7/2$546

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 July 3, 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

Thu 8/14

3:35 pm-10:00 pm

1 stop6h 25m

Chicago Midway

Sun 8/17

9:00 am-1:20 pm

1 stop4h 20m

$203

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Tue 9/2

2:21 pm-9:26 pm

1 stop7h 05m

Chicago Midway

Wed 9/10

6:00 am-10:25 am

1 stop4h 25m

$213

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Tue 8/12

7:43 am-11:48 am

1 stop4h 05m

Chicago Midway

Tue 8/19

6:04 am-10:46 am

1 stop4h 42m

$237

MobileChicago

MOB - MDW

MOBMDW

Mobile

Sat 8/16

4:31 pm-9:12 pm

1 stop4h 41m

Chicago Midway

Sat 8/23

6:04 am-11:27 am

1 stop5h 23m

$245

Baton RougeChicago

BTR - MDW

BTRMDW

Baton Rouge Ryan

Thu 8/21

6:00 am-11:48 am

1 stop5h 48m

Chicago Midway

Fri 8/29

6:00 am-11:00 am

1 stop5h 00m

$249

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 8/23

3:45 pm-9:12 pm

1 stop5h 27m

Chicago Midway

Tue 8/26

4:25 pm-9:38 pm

1 stop5h 13m

$249

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Wed 8/20

7:05 am-2:25 pm

2 stops7h 20m

Chicago Midway

Sun 8/24

7:10 am-2:25 pm

1 stop7h 15m

$277

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Sun 7/27

12:12 pm-9:41 am

2 stops21h 29m

Chicago Midway

Fri 8/1

1:11 pm-7:22 am

2 stops18h 11m

$310

ColumbusChicago

GTR - MDW

GTRMDW

Columbus Golden Triangle Reg.

Fri 7/18

6:00 am-11:58 am

1 stop5h 58m

Chicago Midway

Tue 7/22

1:09 pm-9:35 pm

2 stops8h 26m

$803

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Tue 9/9

1:50 pm-3:30 pm

Nonstop1h 40m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 20 results
1
2

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 July 3, 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.

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 July 3, 2025.
Read through reviews of airlines operating flights from Mississippi to Chicago Midway Airport, such as Southwest, Delta, and Allegiant Air. 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
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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
708 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

7.6

Food

7.0

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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$396FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$338Average$392FlexibilityNo cancel feeOn-time63%

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