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$82+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
MSY — MDW
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheapflights Tip: The best prices from New Orleans Louis Armstrong to Chicago Midway are usually found in February or September, booked 50 days in advance, depart on a Thursday or Saturday and return on a Tuesday

Cheap 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 July 29, 2025.

Round-trip from

$149
(Southwest)

One-way from

$82
(Trip.com)

Popular in

December

Cheapest in

February

Average price

$287

Good round-trip deal

$208 or less

Good one-way deal

$138 or less
From New Orleans Louis Armstrong to Chicago Midway
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One-way flight from New Orleans Louis Armstrong to Chicago Midway
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Highest demand for flights based on searches. 11% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from New Orleans Louis Armstrong to Chicago Midway.
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Price to beat on a one-way flight from New Orleans Louis Armstrong to Chicago Midway.
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Find 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 July 29, 2025.

This Southwest deal was found by Cheapflights users on 7/28. 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.
Thu 9/45:20 pmMSY - MDW
Nonstop2h 15mSouthwest
Mon 9/157:45 amMDW - MSY
Nonstop2h 10mSouthwest
Deal found 7/28$149
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/74:50 pmMSY - MDW
1 stop6h 27mFrontier
Sat 8/99:12 pmMDW - MSY
1 stop22h 10mFrontier
Deal found 7/29$215
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 10/175:52 pmMSY - MDW
1 stop4h 22mDelta
Sun 10/196:00 amMDW - MSY
1 stop6h 10mDelta
Deal found 7/29$217

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 July 29, 2025.
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

Thu 9/4

5:20 pm-7:35 pm

Nonstop2h 15m

Chicago Midway

Mon 9/15

7:45 am-9:55 am

Nonstop2h 10m

$149

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Thu 8/7

4:50 pm-11:17 pm

1 stop6h 27m

Chicago Midway

Sat 8/9

2:44 pm-5:04 pm

1 stop26h 20m

$215

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Fri 10/17

5:52 pm-10:14 pm

1 stop4h 22m

Chicago Midway

Mon 10/20

6:00 am-11:05 am

1 stop5h 05m

$217

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Thu 10/16

4:51 pm-11:25 pm

1 stop6h 34m

$82

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Tue 11/11

12:30 pm-4:55 pm

1 stop4h 25m

$85

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Fri 10/24

4:52 pm-10:14 pm

1 stop5h 22m

$109

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Thu 10/30

8:22 pm-5:02 pm

2 stops20h 40m

$142

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

The best insider tips for New Orleans to Chicago Midway Airport 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 New Orleans to Chicago Midway Airport trip
Airports
MSY

Average TSA security wait times at MSY are around 15 minutes, making it efficient for early morning flights to MDW.

Read more about MSYby Brandon Schultz
MDW

Use the Orange Line train from MDW to reach downtown Chicago in under 30 minutes, a convenient option for arriving travelers.

Read more about MDWby Ramsey Qubein
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 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

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

Use this chart to determine the optimal time to book a round-trip flight from New Orleans to Midway. Price data was last updated on July 25, 2025.

The best time to book flights from New Orleans to Chicago Midway Airport is 50 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, April is the cheapest month in which you can book a flight from New Orleans to Chicago Midway Airport (average of $160). Flying from New Orleans 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 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 July 29, 2025.

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 17% on airfare.

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 July 29, 2025.
See what other customers who have flown with Southwest, Delta, and Frontier 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
4,238 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 3 outbound flights to Chicago Midway per day. 3 airlines have flights to Chicago Midway from New Orleans Louis Armstrong on a regular basis.

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

    According to our current data, Southwest ($149), Frontier ($215), and Delta ($217) offers the cheapest pricing from New Orleans to Chicago Midway Airport. Southwest is priced at 46% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from New Orleans to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $82. Southwest flights start at $85 while deals on Delta start at $109 one-way.

  • 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 $253, our data shows the cheapest flight currently is $77. When looking at the most popular route, (New Orleans Louis Armstrong - Chicago Midway), you can expect to pay $149 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, April is the cheapest month in which you can book a flight from New Orleans to Chicago Midway Airport (average of $160). Flying from New Orleans 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Top 3 airlines flying from New Orleans to Midway

Discover the top 3 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$69Average$206FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$183Average$289FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$287FlexibilityNo cancel feeOn-timeN/A

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