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$79+ Cheap flights from New Orleans (MSY) 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
MSY — MDW
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from New Orleans to Midway

Cheapest flights from New Orleans to Midway
Explore the most affordable flight options available from New Orleans to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This Expedia deal was found by Cheapflights users on 1/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:35 pm
MSY
-
MDW
1 stop18h 51m
Frontier
Sat 2/216:00 am
MDW
-
MSY
1 stop11h 02m
Frontier
Deal found 1/20$160
This Southwest deal was found by Cheapflights users on 1/21. 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 2/282:55 pm
MSY
-
MDW
Nonstop2h 20m
Southwest
Tue 3/38:25 am
MDW
-
MSY
Nonstop2h 30m
Southwest
Deal found 1/21$168
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/126:00 am
MSY
-
MDW
1 stop16h 34m
Frontier
Thu 2/193:00 pm
MDW
-
MSY
1 stop22h 03m
Frontier
Deal found 1/19$171
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/66:55 pm
MSY
-
MDW
1 stop13h 48m
Frontier
Sun 2/86:20 am
MDW
-
MSY
1 stop11h 40m
Frontier
Deal found 1/20$175
This Southwest deal was found by Cheapflights users on 1/20. 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 3/46:45 am
MSY
-
MDW
Nonstop2h 20m
Southwest
Sun 3/85:35 pm
MDW
-
MSY
Nonstop2h 20m
Southwest
Deal found 1/20$177
This Expedia deal was found by Cheapflights users on 1/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/2610:01 am
MSY
-
MDW
1 stop9h 57m
Frontier
Mon 2/26:20 am
MDW
-
MSY
1 stop11h 40m
Frontier
Deal found 1/19$181
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 2/206:10 am
MSY
-
MDW
1 stop16h 15m
Frontier
Sun 2/229:04 pm
MDW
-
MSY
1 stop21h 00m
Frontier
Deal found 1/19$183
This Southwest deal was found by Cheapflights users on 1/21. 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.
Tue 2/244:45 pm
MSY
-
MDW
Nonstop2h 20m
Southwest
Thu 2/267:20 pm
MDW
-
MSY
1 stop5h 05m
Southwest
Deal found 1/21$187
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Sat 2/76:05 am
MSY
-
MDW
2 stops29h 40m
Multiple Airlines
Mon 2/96:20 am
MDW
-
MSY
1 stop11h 40m
Multiple Airlines
Deal found 1/19$189

Find flight deals from New Orleans to Midway

Discover tips and strategies to find the most affordable flight options for your journey from New Orleans (MSY) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$160
(Expedia)

One-way from

$79
(Southwest)

Popular in

January

Cheapest in

February

Average price

$377

Good round-trip deal

$221 or less

Good one-way deal

$173 or less
Provider with most accurate pricing for New Orleans Louis Armstrong-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for New Orleans Louis Armstrong-Chicago Midway flights.
Search Deals
From New Orleans Louis Armstrong to Chicago Midway
Search Deals
One-way flight from New Orleans Louis Armstrong to Chicago Midway
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from New Orleans Louis Armstrong to Chicago Midway.
Search Deals
Price to beat on a one-way flight from New Orleans Louis Armstrong to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from New Orleans 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 January 21, 2026.
Use the filters below to find and compare flights from New Orleans to Chicago Midway Airport that are best for you.

Fly from

New Orleans

Fly to

Midway

Route

Depart

Return

Price

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Tue 2/24

4:45 pm-7:05 pm

Nonstop2h 20m

Chicago Midway

Thu 2/26

7:20 pm-12:25 am

1 stop5h 05m

$187

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Sat 2/28

5:25 am-10:21 am

1 stop4h 56m

Chicago Midway

Tue 3/3

6:00 am-1:19 pm

1 stop7h 19m

$197

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Thu 3/5

6:30 pm-8:50 pm

Nonstop2h 20m

Chicago Midway

Mon 3/9

5:00 pm-11:00 pm

1 stop6h 00m

$207

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Sat 2/28

5:25 am-10:21 am

1 stop4h 56m

Chicago Midway

Sun 3/1

9:34 am-4:09 pm

1 stop6h 35m

$207

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Wed 3/4

2:55 pm-8:40 pm

1 stop5h 45m

Chicago Midway

Sun 3/8

5:35 pm-7:55 pm

Nonstop2h 20m

$207

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Thu 2/26

5:34 pm-10:31 pm

1 stop4h 57m

Chicago Midway

Sat 2/28

6:00 am-1:14 pm

1 stop7h 14m

$207

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Sat 2/28

5:00 am-10:25 am

1 stop5h 25m

Chicago Midway

Tue 3/3

10:15 am-4:30 pm

2 stops6h 15m

$222

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Wed 4/1

7:49 am-12:02 pm

1 stop4h 13m

Chicago Midway

Sun 4/5

12:47 pm-8:15 pm

1 stop7h 28m

$227

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Wed 3/4

6:45 am-9:05 am

Nonstop2h 20m

$79

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Tue 2/24

6:45 am-9:05 am

Nonstop2h 20m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/18

Showing 1-10 of 18 results
1
2

Compare providers for flights from New Orleans to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from New Orleans to Midway in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on New Orleans-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Orleans-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Orleans-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Orleans-Chicago Midway Airport flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New Orleans-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from New Orleans to Midway

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

What is the cheapest month to book a flight from New Orleans to Chicago Midway Airport?

Currently, February is the cheapest month in which you can book a flight from New Orleans to Chicago Midway Airport (average of $104). Flying from New Orleans to Chicago Midway Airport in January is currently the most expensive (average of $254). 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 MSY to MDW?

Find hourly flight availability from New Orleans 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 January 21, 2026.

One of the essential ways to save on airfare from New Orleans to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 33% on airfare.

The best insider tips for New Orleans to Chicago Midway Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your New Orleans to Chicago Midway Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Brandon Schultz

Brandon Schultz

Expert on MSY

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

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 January 21, 2026.
See what other customers who have flown with Southwest and Spirit Airlines from New Orleans to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,364 reviews
Southwest
8.0
Very good
4,266 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from New Orleans to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from New Orleans to Chicago Midway?

    For a flight from New Orleans to Chicago Midway, you will be flying from Louis Armstrong. New Orleans Louis Armstrong (MSY) is just 11.4 mi from the center of the city. Louis Armstrong is the only New Orleans airport and it handles 2 outbound flights to Chicago Midway per day. 2 airlines have flights to Chicago Midway from New Orleans Louis Armstrong on a regular basis.

  • How long is the flight from New Orleans to Chicago Midway Airport?

    A quick flight from New Orleans to Chicago Midway Airport can take about 2h 20m. Southwest provides one of the quickest options available for as low as $187. New Orleans and Chicago Midway Airport are separated by a distance of 827 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from New Orleans to Chicago Midway Airport round-trip?

    According to our current data, Spirit Airlines ($100), and Southwest ($172) offers the cheapest pricing from New Orleans to Chicago Midway Airport. Spirit Airlines is priced at 62% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest flights from New Orleans to Chicago Midway Airport?

    While on average a flight from New Orleans to Chicago Midway Airport is generally $318, our data shows the cheapest flight currently is $98. When looking at the most popular route, (New Orleans Louis Armstrong - Chicago Midway), you can expect to pay $189 for that flight.

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

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

  • How can I find direct flights from New Orleans to Midway?

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

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

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

    Currently, February is the cheapest month in which you can book a flight from New Orleans to Chicago Midway Airport (average of $104). Flying from New Orleans to Chicago Midway Airport in January is currently the most expensive (average of $254). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from New Orleans to Midway

Discover the top 2 airlines that operate flights from New Orleans 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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$100Average$121FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$172Average$267FlexibilityNo cancel feeOn-time63%

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