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$90+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — MDW
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$208
(Booking.com)

One-way from

$90
(Booking.com)

Popular in

January

Cheapest in

October

Average price

$465
Provider with most accurate pricing for Jackson-Evers Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Jackson-Evers Intl-Chicago (CHI) flights.
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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 ($20 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 March 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 March 28, 2025.

This Booking.com deal was found by Cheapflights users on 3/27. 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 4/107:44 pmMEM - MDW
1 stop28h 37mFrontier
Sun 4/136:45 amMDW - MEM
1 stop11h 54mFrontier
Deal found 3/27$208
This Southwest deal was found by Cheapflights users on 3/28. 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.
Fri 4/185:05 amMEM - MDW
Nonstop1h 35mSouthwest
Sun 4/2010:55 pmMDW - MEM
Nonstop1h 45mSouthwest
Deal found 3/28$217
This Delta deal was found by Cheapflights users on 3/27. 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 4/2412:05 pmMEM - MDW
1 stop6h 15mDelta
Thu 5/13:02 pmMDW - MEM
1 stop6h 06mDelta
Deal found 3/27$237
This Delta deal was found by Cheapflights users on 3/27. 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 4/191:14 pmMOB - MDW
1 stop4h 45mDelta
Tue 4/2212:48 pmMDW - MOB
1 stop5h 58mDelta
Deal found 3/27$244
This Delta deal was found by Cheapflights users on 3/27. 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 7/55:00 pmBTR - MDW
1 stop4h 38mDelta
Sat 7/126:00 amMDW - BTR
1 stop6h 45mDelta
Deal found 3/27$249
This Delta deal was found by Cheapflights users on 3/26. 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 5/16:02 pmGPT - MDW
1 stop4h 20mDelta
Tue 5/612:48 pmMDW - GPT
1 stop4h 28mDelta
Deal found 3/26$249
This Delta deal was found by Cheapflights users on 3/26. 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 5/103:06 pmJAN - MDW
1 stop6h 08mDelta
Sat 5/1712:53 pmMDW - JAN
1 stop5h 39mDelta
Deal found 3/26$249
This Southwest deal was found by Cheapflights users on 3/26. 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 5/246:35 pmJAN - MDW
1 stop4h 55mSouthwest
Tue 5/276:50 amMDW - JAN
1 stop7h 00mSouthwest
Deal found 3/26$279
This Mytrip deal was found by Cheapflights users on 3/27. 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.
Wed 5/75:14 pmMEM - MDW
3 stops20h 15mMultiple Airlines
Thu 5/2911:03 amMDW - MEM
3 stops29h 16mMultiple Airlines
Deal found 3/27$597

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 March 28, 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 4/10

7:44 pm-12:21 am

1 stop28h 37m

Chicago Midway

Sun 4/13

6:45 am-6:39 pm

1 stop11h 54m

$208

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Fri 4/18

5:05 am-6:40 am

Nonstop1h 35m

Chicago Midway

Sun 4/20

10:55 pm-12:40 am

Nonstop1h 45m

$217

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Thu 4/24

12:05 pm-6:20 pm

1 stop6h 15m

Chicago Midway

Thu 5/1

3:02 pm-9:08 pm

1 stop6h 06m

$237

MobileChicago

MOB - MDW

MOBMDW

Mobile

Sat 4/19

1:14 pm-5:59 pm

1 stop4h 45m

Chicago Midway

Tue 4/22

12:48 pm-6:46 pm

1 stop5h 58m

$244

Baton RougeChicago

BTR - MDW

BTRMDW

Baton Rouge Ryan

Fri 5/2

5:45 pm-10:22 pm

1 stop4h 37m

Chicago Midway

Mon 5/5

12:48 pm-4:59 pm

1 stop4h 11m

$249

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 5/1

6:02 pm-10:22 pm

1 stop4h 20m

Chicago Midway

Tue 5/6

12:48 pm-5:16 pm

1 stop4h 28m

$249

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sat 5/10

3:06 pm-9:14 pm

1 stop6h 08m

Chicago Midway

Sat 5/17

12:53 pm-6:32 pm

1 stop5h 39m

$249

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Sat 5/24

6:35 pm-11:30 pm

1 stop4h 55m

Chicago Midway

Tue 5/27

6:50 am-1:50 pm

1 stop7h 00m

$279

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Wed 5/7

5:14 pm-1:29 pm

3 stops20h 15m

Chicago Midway

Thu 5/29

11:03 am-4:19 pm

3 stops29h 16m

$597

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Sun 4/27

4:04 pm-7:06 pm

1 stop27h 02m

$90

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/28

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 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.

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 March 28, 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 March 28, 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
8.1
Very good
4,274 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Food

7.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Food

7.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,897 reviews
Southwest
8.1
Very good
4,274 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Food

7.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.1
Very good
4,274 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Food

7.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,271 reviews
Southwest
8.1
Very good
4,274 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Food

7.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 Frontier, with whom users have recently found tickets for as low as $90. However, be on the lookout for offers from Southwest and Delta, 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 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 Mississippi?

Book flights to Mississippi if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Mississippi to Midway

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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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$258Average$456FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$338Average$396FlexibilityNo cancel feeOn-time63%
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