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$114+ Cheap flights from Midway (MDW) to New Orleans (MSY)

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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MSY
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to New Orleans Louis Armstrong are usually found in August or September, booked 63 days in advance, depart on a Saturday or Monday and return on a Thursday

Cheap flight deals from Midway to New Orleans

Cheapest flights from Midway to New Orleans
Explore the most affordable flight options available from Midway to New Orleans. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 10, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Tue 6/26:00 am
MDW
-
MSY
1 stop10h 21m
Frontier
Tue 6/95:21 pm
MSY
-
MDW
1 stop17h 48m
Frontier
Deal found 5/5$201
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 5/286:00 am
MDW
-
MSY
1 stop10h 21m
Frontier
Mon 6/15:21 pm
MSY
-
MDW
1 stop28h 41m
Frontier
Deal found 5/8$204
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 5/286:00 am
MDW
-
MSY
1 stop10h 21m
Frontier
Tue 6/25:21 pm
MSY
-
MDW
1 stop28h 41m
Frontier
Deal found 5/8$205
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 5/276:00 am
MDW
-
MSY
1 stop10h 21m
Frontier
Fri 5/295:21 pm
MSY
-
MDW
1 stop28h 41m
Frontier
Deal found 5/9$207
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 5/286:00 am
MDW
-
MSY
1 stop10h 21m
Frontier
Sun 5/315:21 pm
MSY
-
MDW
1 stop17h 48m
Frontier
Deal found 5/5$210
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 5/286:00 am
MDW
-
MSY
2 stops15h 48m
Multiple Airlines
Mon 6/15:21 pm
MSY
-
MDW
1 stop17h 51m
Multiple Airlines
Deal found 5/5$226
This Frontier deal was found by Cheapflights users on 5/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:40 am
MDW
-
MSY
1 stop9h 27m
Frontier
Tue 10/274:58 pm
MSY
-
MDW
1 stop4h 55m
Frontier
Deal found 5/6$230
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/36:00 am
MDW
-
MSY
1 stop10h 21m
Frontier
Sat 6/65:21 pm
MSY
-
MDW
1 stop17h 51m
Frontier
Deal found 5/5$237

Find flight deals from Midway to New Orleans

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to New Orleans (MSY). 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 May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$201
(Kiwi.com)

One-way from

$114
(Kiwi.com)

Popular in

April

Cheapest in

August

Average price

$328

Good round-trip deal

$367 or less

Good one-way deal

$245 or less
Provider with most accurate pricing for Chicago Midway-New Orleans Louis Armstrong flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-New Orleans Louis Armstrong flights.
Search Deals
From Chicago Midway to New Orleans Louis Armstrong
Search Deals
One-way flight from Chicago Midway to New Orleans Louis Armstrong
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($65 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to New Orleans Louis Armstrong.
Search Deals
Price to beat on a one-way flight from Chicago Midway to New Orleans Louis Armstrong.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to New Orleans 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 May 10, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to New Orleans that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Fri 5/29

9:50 pm-12:10 am

Nonstop2h 20m

New Orleans Louis Armstrong

Tue 6/2

8:00 am-10:20 am

Nonstop2h 20m

$306

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Thu 5/28

5:40 pm-11:35 pm

2 stops5h 55m

New Orleans Louis Armstrong

Mon 6/1

5:10 am-7:30 am

Nonstop2h 20m

$333

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Fri 5/29

9:50 pm-12:10 am

Nonstop2h 20m

New Orleans Louis Armstrong

Sun 5/31

6:35 pm-8:55 pm

Nonstop2h 20m

$363

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Wed 6/3

8:35 pm-10:55 pm

Nonstop2h 20m

New Orleans Louis Armstrong

Tue 6/9

6:10 am-10:45 am

1 stop4h 35m

$365

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Wed 6/24

9:05 pm-11:20 pm

Nonstop2h 15m

New Orleans Louis Armstrong

Sat 6/27

5:45 am-8:05 am

Nonstop2h 20m

$367

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Tue 6/9

2:50 pm-5:05 pm

Nonstop2h 15m

New Orleans Louis Armstrong

Fri 6/12

5:15 pm-7:30 pm

Nonstop2h 15m

$367

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Fri 6/26

9:40 pm-11:55 pm

Nonstop2h 15m

New Orleans Louis Armstrong

Mon 6/29

5:40 am-8:00 am

Nonstop2h 20m

$379
Quickest round-trip

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Fri 8/7

3:00 pm-5:10 pm

Nonstop2h 10m

New Orleans Louis Armstrong

Mon 8/10

5:00 am-7:15 am

Nonstop2h 15m

$379

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Wed 6/24

9:54 am-3:25 pm

1 stop5h 31m

New Orleans Louis Armstrong

Mon 6/29

10:41 am-3:40 pm

1 stop4h 59m

$387

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Sat 6/6

9:23 am-3:20 pm

1 stop5h 57m

New Orleans Louis Armstrong

Tue 6/9

6:23 am-12:05 pm

1 stop5h 42m

$397

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/8

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Midway to New Orleans

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 Midway to New Orleans in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 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 Chicago Midway Airport-New Orleans flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-New Orleans flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-New Orleans flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-New Orleans flights, Cheapflights users trust FlightHub the most. FlightHub 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 Chicago Midway Airport-New Orleans 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 Midway to New Orleans

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

How far ahead should I book a flight from Chicago Midway Airport to New Orleans?

Booking 62 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago Midway Airport to New Orleans. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to New Orleans (average of $199). Flying from Chicago Midway Airport to New Orleans in April is currently the most expensive (average of $433). 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 MDW to MSY?

Find hourly flight availability from Midway to New Orleans. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 10, 2026.

It’s optimal to fly from Chicago Midway Airport to New Orleans in the evening. By choosing this option you can save up to 13% on the cost of your flight, compared to a flight in the afternoon.

What is the cheapest day to fly from Chicago Midway Airport to New Orleans?

Use this chart to determine the cheapest time to fly round-trip from Midway to New Orleans. Price data was last updated on May 9, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to New Orleans flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Chicago Midway Airport to New Orleans?

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

Get insights into the airlines that provide service to New Orleans. 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 New Orleans. Reviews last updated May 10, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andFrontier from Chicago Midway Airport to New Orleans by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,301 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,301 reviews
Southwest
7.9
Good
4,301 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,454 reviews
Southwest
7.9
Good
4,301 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.6
Fair
2,955 reviews
Southwest
7.9
Good
4,301 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Midway to New Orleans. 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 into for flights to New Orleans from Chicago Midway?

    Located just 11.4 mi from the city center, New Orleans Louis Armstrong is the airport most travelers will use when flying to New Orleans from Chicago Midway. Booking flights from Chicago Midway to Louis Armstrong (MSY) should be relatively easy as there are 2 daily inbound flights from Chicago Midway from 3 different airlines.

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

    A quick flight from Chicago Midway Airport to New Orleans can take about 2h 20m. Southwest provides one of the quickest options available for as low as $306. The distance between Chicago Midway Airport and New Orleans is about 827 mi. All flights are typically nonstop.

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

    Cheapflights users have booked flights from Chicago Midway Airport to New Orleans round-trip from $102. Other airlines that can offer you cheap pricing are Southwest, from $166, and Delta, from $197. Users have found that Frontier is 67% cheaper than the other options available to this destination.

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

    While on average a flight from Chicago Midway Airport to New Orleans is generally $344, our data shows the cheapest flight currently is $118. When looking at the most popular route, (Chicago Midway - New Orleans Louis Armstrong), you can expect to pay $257 for that flight.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to New Orleans (average of $199). Flying from Chicago Midway Airport to New Orleans in April is currently the most expensive (average of $433). 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 New Orleans?

Book flights to New Orleans if you plan to visit one of these locations
Metairie
Kenner
Gonzales
Houma
Covington
Gretna
Slidell
Thibodaux
Hammond

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Top 3 airlines flying from Midway to New Orleans

Discover the top 3 airlines that operate flights from Midway to New Orleans. 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 May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$102Average$247FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$166Average$337FlexibilityNo cancel feeOn-time63%
DeltaCheapest$197Average$383FlexibilityNo cancel feeOn-timeN/A

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