MDW - MSY

$106 Find Cheap Flights from Chicago Midway Airport to New Orleans - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to New Orleans departing on 10/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Everything you should know

Cheapest round-trip
$217
Typical prices: $236-$389
Delta
Wed 8/19Thu 8/20
MDW - MSY • 1 stop
Cheapest non-stop
$221
Typical prices: $224-$357
Southwest
Fri 9/11Mon 9/14
MDW - MSY • Non-stop
Top airlines
Cheapest • from $217 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 12m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 80% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $441 (round-trip)
Shortest trip • 5h 01m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 42% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 25% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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We hope you love your trip to New Orleans!
Flight Deals
Booking Insights
Expert advice
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to New Orleans that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to New Orleans

Wed, Aug 19 - Thu, Aug 20
Delta Logo
10:54 am - 6:10 pm
MDW
-
MSY
7h 16m
1 stop
Delta Logo
5:12 am - 11:51 am
MSY
-
MDW
6h 39m
1 stop
$217Delta
Sat, Oct 17 - Wed, Oct 21
Delta Logo
9:29 am - 4:08 pm
MDW
-
MSY
6h 39m
1 stop
Delta Logo
6:25 am - 11:50 am
MSY
-
MDW
5h 25m
1 stop
$217Delta
Thu, Aug 20 - Sat, Aug 22
Southwest Logo
7:15 am - 9:25 am
MDW
-
MSY
2h 10mnonstop
Southwest Logo
3:20 pm - 7:20 pm
MSY
-
MDW
4h 00m
1 stop
$217Southwest
Sat, Dec 5 - Mon, Dec 7
Southwest Logo
6:15 pm - 8:40 pm
MDW
-
MSY
2h 25mnonstop
Southwest Logo
6:15 pm - 10:40 pm
MSY
-
MDW
4h 25m
1 stop
$217Southwest
Wed, Sep 16 - Sat, Sep 19
Southwest Logo
10:15 am - 4:50 pm
MDW
-
MSY
6h 35m
1 stop
Southwest Logo
3:20 pm - 7:20 pm
MSY
-
MDW
4h 00m
1 stop
$217Southwest
Sat, Oct 24 - Tue, Oct 27
Delta Logo
4:19 pm - 11:35 pm
MDW
-
MSY
7h 16m
1 stop
Delta Logo
6:02 pm - 10:33 pm
MSY
-
MDW
4h 31m
1 stop
$217Delta
Tue, Sep 29 - Sat, Oct 3
Delta Logo
5:11 pm - 11:37 pm
MDW
-
MSY
6h 26m
1 stop
Delta Logo
11:20 am - 6:22 pm
MSY
-
MDW
7h 02m
1 stop
$217Delta
Mon, Oct 12 - Sat, Oct 17
Frontier Logo
6:40 am - 4:07 pm
MDW
-
MSY
9h 27m
1 stop
Frontier Logo
5:02 pm - 9:58 pm
MSY
-
MDW
4h 56m
1 stop
$221Frontier
Mon, Nov 9 - Thu, Nov 12
Frontier Logo
7:25 am - 4:03 pm
MDW
-
MSY
8h 38m
1 stop
Frontier Logo
4:58 pm - 9:53 pm
MSY
-
MDW
4h 55m
1 stop
$222Frontier
Thu, Oct 22 - Tue, Oct 27
Frontier Logo
6:40 am - 4:07 pm
MDW
-
MSY
9h 27m
1 stop
Frontier Logo
4:58 pm - 9:53 pm
MSY
-
MDW
4h 55m
1 stop
$228Frontier
Booking Insights

KAYAK's insights & trends for Midway to New Orleans flights

Get data-powered insights and trends into flights from Midway to New Orleans to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago Midway Airport to New Orleans?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to New Orleans departing in September.

Flight prices are below average for this route right now.

Flights to New Orleans from Chicago Midway Airport usually cost between $236 and $389 in September.
The lowest price found in the past 5 days was $217 on Southwest (Sep 5-Sep 8).

What’s the cheapest day of the week to fly from Chicago Midway Airport to New Orleans?

The average price of all round-trip flights from Chicago Midway Airport to New Orleans clicked on KAYAK for each day over the last 12 months.

When flying from Chicago Midway Airport to New Orleans, you should consider leaving on a Tuesday and avoid Thursdays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Tuesdays and the most expensive ones on Mondays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to New Orleans, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to New Orleans is January, where tickets cost $257 (return) on average. On the other hand, the most expensive months are July and April, where the average cost of round-trip tickets is $441 and $412 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to New Orleans?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $317, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to New Orleans, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to New Orleans, you should book around 3 weeks before departure, which saves you about 42% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Expert advice

Expert advice for your flight from Midway to New Orleans

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Daniel Scheffler

Daniel Scheffler

Expert on MSY

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Good to know

Low season

August

Cheapest flight

$106
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Chicago Midway Airport to New Orleans

When to book flights from Midway to New Orleans

Are your dates flexible? Find out the best times to travel from Midway to New Orleans based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to New Orleans flights

  • What is the cheapest flight from Chicago Midway Airport to New Orleans?

    In the last 5 days, the lowest price for a flight from Chicago Midway Airport to New Orleans was $106 for a one-way ticket and $217 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and New Orleans?

    No

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to New Orleans?

    American Airlines, JetBlue, and Delta offer inflight Wi-Fi service on the Chicago Midway Airport to New Orleans flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to New Orleans?

    The Embraer 175 is the aircraft model that flies most regularly on the Chicago Midway Airport to New Orleans flight route.

  • On which days can I fly direct from Chicago Midway Airport to New Orleans?

    There are nonstop flights from Chicago Midway Airport to New Orleans on a daily basis.

  • Which is the best airline for flights from Chicago to New Orleans, Southwest or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to New Orleans are Southwest and Frontier. With an average price for the route of $394 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $264 and an overall rating of 5.6.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to New Orleans?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to New Orleans.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to New Orleans?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to New Orleans from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to New Orleans?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to New Orleans with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and MSY can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to New Orleans?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to New Orleans from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to New Orleans

  • Looking for a cheap flight? 25% of our users found flights on this route for $176 or less one-way and $265 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to New Orleans?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to New Orleans Louis Armstrong.
Find which airlines fly direct from Chicago Midway Airport to New Orleans Louis Armstrong Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to New Orleans Louis Armstrong

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

New Orleans Louis Armstrong to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airlines flying from Midway to New Orleans

 
See real verified KAYAK customer reviews for airlines flying from Chicago to New Orleans. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to New Orleans? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4230 reviews
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

Exceptional crew! Friendly and professional. Pleasant attitude and treated everyone with respect.

I like the boarding procedure. A bumpy ride, but it couldn't be helped. Please make sure the exit seats are clearly indicated.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

On both our outgoing flight and our return flight, Frontier split up our seats. We were two adults and two small children, one an infant. Both flights were only about half full with full rows of empty seats. Yet, the airline split us up. No, we did not spend the extra $40 per person each way to purchase seat assignments ahead of time. But should we have to do this? If so, then the advertised ticket price was $40 off. What makes this even more egregious is that the plane was not full. So, there was no reason for Frontier to split up our group other than to extract an extra $320. A stewardess even had the nerve to tell me “if you want your family to sit together, I recommend that you purchase seat assignments next time.” On a half empty flight? Ridiculous. We will not be flying Frontier again.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Everything you need to know for your flight from Midway to New Orleans

Information on your arrival and departure airports