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$84+ 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MSY
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to New Orleans Louis Armstrong are usually found in June or July, booked 64 days in advance, depart on a Tuesday or Monday and return on a Thursday

Cheap 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 August 14, 2025.

Round-trip from

$144
(Priceline)

One-way from

$84
(FlightHub)

Popular in

February

Cheapest in

June

Average price

$347

Good round-trip deal

$173 or less

Good one-way deal

$148 or less
From Chicago Midway to New Orleans Louis Armstrong
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One-way flight from Chicago Midway to New Orleans Louis Armstrong
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Highest demand for flights based on searches. 11% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago Midway to New Orleans Louis Armstrong.
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Price to beat on a one-way flight from Chicago Midway to New Orleans Louis Armstrong.
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Find 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 August 14, 2025.

This Priceline deal was found by Cheapflights users on 8/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/116:20 amMDW - MSY
1 stop9h 30mFrontier
Thu 9/184:51 pmMSY - MDW
1 stop6h 29mFrontier
Deal found 8/14$144
This Priceline deal was found by Cheapflights users on 8/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/56:20 amMDW - MSY
1 stop9h 37mFrontier
Sun 9/79:07 pmMSY - MDW
1 stop10h 04mFrontier
Deal found 8/14$147
This Southwest deal was found by Cheapflights users on 8/13. 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.
Mon 9/228:00 pmMDW - MSY
Nonstop2h 10mSouthwest
Thu 9/256:30 amMSY - MDW
Nonstop2h 15mSouthwest
Deal found 8/13$149
This Frontier deal was found by Cheapflights users on 8/14. 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.
Mon 9/158:15 amMDW - MSY
1 stop10h 42mFrontier
Mon 9/224:52 pmMSY - MDW
1 stop6h 28mFrontier
Deal found 8/14$156
This Southwest deal was found by Cheapflights users on 8/14. 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 9/107:20 pmMDW - MSY
Nonstop2h 10mSouthwest
Sat 9/136:25 amMSY - MDW
Nonstop2h 15mSouthwest
Deal found 8/14$159
This FlightHub deal was found by Cheapflights users on 8/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/58:15 amMDW - MSY
1 stop10h 42mFrontier
Thu 9/114:51 pmMSY - MDW
1 stop23h 09mFrontier
Deal found 8/14$163
This Southwest deal was found by Cheapflights users on 8/14. 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 9/41:20 pmMDW - MSY
Nonstop2h 15mSouthwest
Sun 9/76:40 amMSY - MDW
Nonstop2h 15mSouthwest
Deal found 8/14$169
This FlightHub deal was found by Cheapflights users on 8/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/79:15 amMDW - MSY
1 stop6h 09mFrontier
Sun 11/97:19 pmMSY - MDW
1 stop19h 14mFrontier
Deal found 8/14$172
This Priceline deal was found by Cheapflights users on 8/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/139:44 amMDW - MSY
1 stop6h 53mFrontier
Fri 10/175:22 pmMSY - MDW
1 stop6h 03mFrontier
Deal found 8/14$173
This Frontier deal was found by Cheapflights users on 8/14. 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.
Fri 10/38:15 amMDW - MSY
1 stop10h 42mFrontier
Sun 10/54:51 pmMSY - MDW
1 stop6h 29mFrontier
Deal found 8/14$175
This Frontier deal was found by Cheapflights users on 8/14. 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.
Sun 9/286:20 amMDW - MSY
1 stop9h 30mFrontier
Sun 10/59:07 pmMSY - MDW
1 stop10h 04mFrontier
Deal found 8/14$176
This Southwest deal was found by Cheapflights users on 8/14. 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 9/66:35 amMDW - MSY
1 stop6h 45mSouthwest
Mon 9/85:20 pmMSY - MDW
Nonstop2h 15mSouthwest
Deal found 8/14$179

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 August 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to New Orleans that are best for you.

Fly from

Midway

Fly to

New Orleans

Route

Depart

Return

Price

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Mon 9/8

6:20 am-3:57 pm

1 stop9h 37m

New Orleans Louis Armstrong

Fri 9/12

4:52 pm-11:20 pm

1 stop6h 28m

$144

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Thu 9/11

6:20 am-3:50 pm

1 stop9h 30m

New Orleans Louis Armstrong

Thu 9/18

4:51 pm-11:20 pm

1 stop6h 29m

$144

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Thu 9/11

6:20 am-3:50 pm

1 stop9h 30m

New Orleans Louis Armstrong

Fri 9/19

4:52 pm-11:20 pm

1 stop6h 28m

$144

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Fri 9/19

6:20 am-3:57 pm

1 stop9h 37m

New Orleans Louis Armstrong

Mon 9/22

4:52 pm-11:20 pm

1 stop6h 28m

$144

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Thu 9/11

6:20 am-3:50 pm

1 stop9h 30m

New Orleans Louis Armstrong

Mon 9/15

4:52 pm-11:20 pm

1 stop6h 28m

$144

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Thu 9/4

6:20 am-3:50 pm

1 stop9h 30m

New Orleans Louis Armstrong

Mon 9/8

4:52 pm-11:20 pm

1 stop6h 28m

$144

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Mon 9/22

6:20 am-3:57 pm

1 stop9h 37m

New Orleans Louis Armstrong

Fri 9/26

4:52 pm-11:20 pm

1 stop6h 28m

$144

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Thu 9/11

6:20 am-3:50 pm

1 stop9h 30m

New Orleans Louis Armstrong

Sun 9/14

9:07 pm-7:11 am

1 stop10h 04m

$147

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Fri 9/26

8:15 am-6:57 pm

1 stop10h 42m

New Orleans Louis Armstrong

Mon 9/29

4:52 pm-11:20 pm

1 stop6h 28m

$147

ChicagoNew Orleans

MDW - MSY

MDWMSY

Chicago Midway

Fri 9/12

6:20 am-3:57 pm

1 stop9h 37m

New Orleans Louis Armstrong

Sun 9/14

9:07 pm-7:11 am

1 stop10h 04m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 19 results
1
2

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

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to New Orleans trip
Airports
MDW

Use the airport’s mobile system to order food directly to your gate, saving time and ensuring you don't miss boarding.

Read more about MDWby Ramsey Qubein
MSY

For quick access to downtown, take the Regional Transit Authority express bus, which takes about 40 minutes from MSY.

Read more about MSYby Brandon Schultz
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

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

Brandon Schultz

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

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?

Use this chart to determine the optimal time to book a round-trip flight from Midway to New Orleans. Price data was last updated on August 8, 2025.

Booking 63 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 $256). Flying from Chicago Midway Airport to New Orleans in April is currently the most expensive (average of $343). 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 August 14, 2025.

It’s optimal to fly from Chicago Midway Airport to New Orleans in the afternoon. By choosing this option you can save up to 9% on the cost of your flight, compared to a flight at noon.

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 August 10, 2025.

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

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 August 14, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines 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
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 is 1 daily inbound flight from Chicago Midway from 3 different airlines.

  • 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 $178. Other airlines that can offer you cheap pricing are United Airlines, from $197, and Delta, from $216. Users have found that Southwest is 49% 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 $253, our data shows the cheapest flight currently is $78. When looking at the most popular route, (Chicago Midway - New Orleans Louis Armstrong), you can expect to pay $149 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 $256). Flying from Chicago Midway Airport to New Orleans in April is currently the most expensive (average of $343). 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
Slidell
Houma
Covington
Thibodaux
Gretna
Hammond
Gonzales

Browse thousands of different options on Cheapflights for your next trip

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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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$178Average$355FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$197Average$518FlexibilityNo cancel feeOn-time69%
DeltaCheapest$216Average$316FlexibilityNo cancel feeOn-timeN/A

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