$59 Cheap Flights from Chicago (MDW) to New Orleans (MSY)

View $59 flight on Mon, Nov 10, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY)

Cheap Flights from Chicago to New Orleans (MDW-MSY)

Prices were available within the past 7 days and start at $59 for one-way flights and $139 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Nov 15 - Tue, Nov 18
MDW
Chicago
MSY
New Orleans
$139 Roundtrip, found 15 hours ago
$139
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Chicago to New Orleans, returning Tue, Nov 18, priced at $139 found 15 hours ago
Frontier Airlines
Mon, Oct 27 - Fri, Oct 31
MDW
Chicago
MSY
New Orleans
$139 Roundtrip, found 23 hours ago
$139
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Mon, Oct 27 from Chicago to New Orleans, returning Fri, Oct 31, priced at $139 found 23 hours ago
Frontier Airlines
Mon, Nov 3 - Wed, Nov 5
MDW
Chicago
MSY
New Orleans
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Nov 3 from Chicago to New Orleans, returning Wed, Nov 5, priced at $149 found 1 day ago
Frontier Airlines
Mon, Oct 27 - Thu, Nov 13
MDW
Chicago
MSY
New Orleans
$154 Roundtrip, found 23 hours ago
$154
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Mon, Oct 27 from Chicago to New Orleans, returning Thu, Nov 13, priced at $154 found 23 hours ago
Southwest Airlines
Sat, Nov 15 - Wed, Nov 19
MDW
Chicago
MSY
New Orleans
$157 Roundtrip, found 1 hour ago
$157
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sat, Nov 15 from Chicago to New Orleans, returning Wed, Nov 19, priced at $157 found 1 hour ago
Southwest Airlines
Tue, Dec 2 - Sat, Dec 6
MDW
Chicago
MSY
New Orleans
$158 Roundtrip, found 22 hours ago
$158
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Tue, Dec 2 from Chicago to New Orleans, returning Sat, Dec 6, priced at $158 found 22 hours ago
Frontier Airlines
Sun, Nov 2 - Fri, Nov 14
MDW
Chicago
MSY
New Orleans
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Nov 2 from Chicago to New Orleans, returning Fri, Nov 14, priced at $160 found 1 day ago
Southwest Airlines
Mon, Nov 17 - Wed, Nov 19
MDW
Chicago
MSY
New Orleans
$163 Roundtrip, found 5 hours ago
$163
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Mon, Nov 17 from Chicago to New Orleans, returning Wed, Nov 19, priced at $163 found 5 hours ago
Southwest Airlines
Tue, Dec 2 - Fri, Dec 5
MDW
Chicago
MSY
New Orleans
$164 Roundtrip, found 2 days ago
$164
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Dec 2 from Chicago to New Orleans, returning Fri, Dec 5, priced at $164 found 2 days ago
Southwest Airlines
Wed, Feb 18 - Wed, Feb 25
MDW
Chicago
MSY
New Orleans
$167 Roundtrip, found 4 hours ago
$167
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Wed, Feb 18 from Chicago to New Orleans, returning Wed, Feb 25, priced at $167 found 4 hours ago

Find the cheapest month to fly from Chicago (MDW) to New Orleans (MSY)

September is typically the cheapest month to fly

From $125 - $301 per traveler.

Alternative airports near New Orleans

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Louis Armstrong New Orleans Intl. MSY. Cheapest option available. Average driving time to city center is 20 minutes. Flights from $244
MSY
Louis Armstrong New Orleans Intl.
Cheapest
Average driving time to city center20 min
Flights from $244

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY) cost?
Lock in a cheap one-way flight from $59 or cheap return flight from $139 from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY)?
The cheapest month to fly from MDW to MSY is November, when there's less demand. Off-peak months are typically when airlines offer better prices between these airports.
Which airlines fly direct from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY)?
Fly nonstop from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY) on a Southwest Airlines flight.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find the carrier with the cheapest MDW to MSY flight.
How many flights per day from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY)?
Every day, an average of 2 direct flights take off from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY). Select the departure time that best fits your itinerary.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY)?
More passengers fly between MDW and MSY at 9 AM than at any other time of day. Rather go when it's quieter? Consider flying outside peak hours and it's possible you'll save on your ticket as well.
What day of the week has the most flights from MDW to MSY?
If you depart on a Friday, you'll get the greatest range of choices for flights from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY).
What is the earliest flight from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY)?
Take the earliest flight at around 8:35AM UTC-6, heading out of Midway Intl. Airport (MDW). You'll be in the air for approximately 2h 25m, arriving at Louis Armstrong New Orleans Intl. Airport (MSY) at approximately 11:00AM UTC-6.
How long does it take to fly from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY)?
Flights from MDW to MSY have an average travel time of 2 hours and 23 minutes. The total distance between these two airports is 830 mi.
What airline has the least delays from MDW to MSY?
Southwest Airlines has the strongest track record for on-time direct flights from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY), with an on-time score of 81%. Use the Expedia App to check your journey status before you leave and get immediate updates about any changes.
What is the best time to fly from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY)?
Opt for a flight from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY) that leaves before 3 PM to reduce the risk of cancellations. Departures after this hour have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for New Orleans from Midway Intl. Airport (MDW)?
Louis Armstrong New Orleans Intl. Airport (MSY) is the only airport in New Orleans with direct flights from Midway Intl. Airport (MDW). Check out the options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY) last-minute?
Booking your ticket from MDW to MSY just before your getaway is usually more expensive. However, if you're flexible with your travel dates and times, you could grab a cheap last-minute fare.
Is it cheaper to book a MDW to MSY flight and hotel package?
You'll typically save money by securing a MDW to MSY flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. After choosing your ideal flights and accommodations, you can add extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Louis Armstrong New Orleans Intl. Airport (MSY)?
Usually, it's possible to reschedule or cancel your MDW to MSY flight. However, if it's been more than 24 hours since booking, additional charges may apply. Check your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Louis Armstrong New Orleans Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$118
Distance
827 mi
Average flight time
2 hours 15 mins

Book with confidence

Chicago to New Orleans Flights

The cheapest times to fly from Chicago to New Orleans

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to New Orleans are during the month of November. You can find some of the cheapest flights from Chicago to New Orleans with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to New Orleans

Sunday is one of the best days to book for cheap flights from Chicago to New Orleans: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to New Orleans

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to New Orleans in 2025. You can also book with separate airlines for your outbound and return journeys, from $59 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to New Orleans flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to New Orleans airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to New Orleans Flights

Explore a world of travel with Expedia

*Available to One Key members.