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

This Southwest deal was found by Cheapflights users on 10/29. 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 12/43:00 pmMEM - MDW
Nonstop1h 35mSouthwest
Mon 12/88:40 pmMDW - MEM
Nonstop1h 45mSouthwest
Deal found 10/29$231
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.
Sun 11/162:30 pmMEM - MDW
1 stop24h 52mMultiple Airlines
Wed 11/191:56 pmMDW - MEM
2 stops28h 35mMultiple Airlines
Deal found 10/30$243
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/201:41 pmMEM - MDW
1 stop23h 40mMultiple Airlines
Sat 11/226:15 pmMDW - MEM
2 stops19h 45mMultiple Airlines
Deal found 10/29$248
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 12/97:39 amBTR - MDW
1 stop4h 16mDelta
Sat 12/1311:05 amMDW - BTR
1 stop5h 21mDelta
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.
Wed 12/245:21 pmGPT - MDW
1 stop5h 01mDelta
Sat 12/276:00 amMDW - GPT
1 stop4h 40mDelta
Deal found 10/28$249
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.
Fri 11/212:30 pmMEM - MDW
2 stops10h 35mMultiple Airlines
Mon 11/245:47 pmMDW - MEM
1 stop15h 15mMultiple Airlines
Deal found 10/30$250
This Delta deal was found by Cheapflights users on 10/29. 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 12/117:21 pmMEM - MDW
1 stop4h 26mDelta
Sat 12/136:00 amMDW - MEM
1 stop5h 42mDelta
Deal found 10/29$251
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/201:41 pmMEM - MDW
1 stop23h 40mMultiple Airlines
Sun 11/235:30 amMDW - MEM
2 stops8h 30mMultiple Airlines
Deal found 10/29$254
This Delta deal was found by Cheapflights users on 10/27. 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.
Wed 12/107:17 pmMOB - MDW
1 stop4h 30mDelta
Sat 12/136:00 amMDW - MOB
1 stop6h 40mDelta
Deal found 10/27$255
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/199:33 pmMEM - MDW
2 stops24h 44mMultiple Airlines
Wed 11/265:30 pmMDW - MEM
1 stop16h 33mMultiple Airlines
Deal found 10/29$258
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/201:41 pmMEM - MDW
1 stop23h 40mMultiple Airlines
Tue 11/255:30 amMDW - MEM
2 stops27h 32mMultiple Airlines
Deal found 10/29$259
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/199:33 pmMEM - MDW
2 stops24h 44mMultiple Airlines
Mon 11/245:47 pmMDW - MEM
1 stop15h 15mMultiple Airlines
Deal found 10/29$261

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$231
(Southwest)

One-way from

$55
(Priceline)

Popular in

January

Cheapest in

September

Average price

$426
Provider with most accurate pricing for Jackson-Evers Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jackson-Evers Intl-Chicago (CHI) flights.
Search Deals
From Mississippi to Chicago Midway
Search Deals
One-way flight from Mississippi to Chicago Midway
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 30, 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 12/4

7:30 am-9:05 am

Nonstop1h 35m

Chicago Midway

Mon 12/8

8:10 am-9:55 am

Nonstop1h 45m

$231

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Fri 12/5

12:10 pm-1:59 pm

2 stops25h 49m

Chicago Midway

Sun 12/7

12:18 pm-7:12 pm

1 stop6h 54m

$241

Baton RougeChicago

BTR - MDW

BTRMDW

Baton Rouge Ryan

Tue 12/9

7:39 am-11:55 am

1 stop4h 16m

Chicago Midway

Sat 12/13

11:05 am-4:26 pm

1 stop5h 21m

$249

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 1/15

4:00 pm-10:09 pm

1 stop6h 09m

Chicago Midway

Mon 1/19

10:46 am-5:17 pm

1 stop6h 31m

$249

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 12/24

5:21 pm-10:22 pm

1 stop5h 01m

Chicago Midway

Sat 12/27

6:00 am-10:40 am

1 stop4h 40m

$249

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Thu 12/11

7:21 pm-11:47 pm

1 stop4h 26m

Chicago Midway

Sat 12/13

6:00 am-11:42 am

1 stop5h 42m

$251

MobileChicago

MOB - MDW

MOBMDW

Mobile

Wed 12/10

7:17 pm-11:47 pm

1 stop4h 30m

Chicago Midway

Sat 12/13

6:00 am-12:40 pm

1 stop6h 40m

$255

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Wed 11/19

9:33 pm-10:17 pm

2 stops24h 44m

Chicago Midway

Mon 11/24

5:47 pm-9:02 am

1 stop15h 15m

$261

Baton RougeChicago

BTR - MDW

BTRMDW

Baton Rouge Ryan

Wed 11/19

7:39 am-11:52 am

1 stop4h 13m

Chicago Midway

Sat 11/22

4:28 pm-9:52 pm

1 stop5h 24m

$274

MobileChicago

MOB - MDW

MOBMDW

Mobile

Fri 12/12

7:17 pm-11:47 pm

1 stop4h 30m

Chicago Midway

Sun 12/14

6:00 am-12:43 pm

1 stop6h 43m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 60 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 October 30, 2025.

One of the essential ways to save on airfare from Mississippi to Chicago Midway Airport is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 26% on airfare.

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 Jackson-Evers Intl - Chicago Midway or Mobile - 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.

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
Porter
Benton Harbor

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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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Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Seattle to O'Hare Intl flights
Denver to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Boston to O'Hare Intl flights
Atlanta to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Baltimore to Midway flights
Dallas/Fort Worth to Midway flights
Ontario to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Los Angeles to Midway flights
Hobby to Midway flights
Atlanta to Midway flights
LaGuardia to Midway flights
Newark to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Denver to Midway flights
Philadelphia to Midway flights
Charlotte to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
San Francisco to Midway flights
George Bush Intcntl to O'Hare Intl flights
Dulles Intl to Midway flights
Hobby to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Minneapolis to Midway flights
Raleigh to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Reagan-National to Midway flights
Austin to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Love Field to O'Hare Intl flights
Hartford to O'Hare Intl flights
Orlando to O'Hare Intl flights
San Diego to O'Hare Intl flights
Portland to O'Hare Intl flights
Boston to Midway flights
Providence to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Columbus to O'Hare Intl 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$379FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$234Average$406FlexibilityNo cancel feeOn-time63%

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