MSY - MDW

$101 Find Cheap Flights from New Orleans to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New Orleans to Midway departing on 5/13. 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.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New Orleans to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New Orleans to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$201
Typical prices: $420-$292
Multiple Airlines
Wed 5/13Sat 5/16
MSY - MDW • 2 stops
Cheapest non-stop
$257
Typical prices: $386-$288
Southwest
Thu 5/28Thu 5/28
MSY - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
MSY offers free Wi-Fi throughout the airport.
Take the CTA Orange Line from MDW to downtown Chicago.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $206 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with Southwest. Average duration is 2h 20m
Direct flights
Direct flights
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Direct flights
Direct flights
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When to travel
Cheapest • 21% price drop
Most popular
Good to know
Good to know
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
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Expert advice
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New Orleans to Midway 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 New Orleans to Midway

Wed, May 13 - Sat, May 16
Multiple Airlines Logo
7:00 am - 10:02 pm
MSY
-
MDW
15h 02m
2 stops
Multiple Airlines Logo
3:07 pm - 5:12 pm
MDW
-
MSY
26h 05m
1 stop
$201Multiple Airlines
Sat, May 30 - Wed, Jun 3
Frontier Logo
5:21 pm - 11:12 am
MSY
-
MDW
17h 51m
1 stop
Frontier Logo
6:00 am - 4:21 pm
MDW
-
MSY
10h 21m
1 stop
$206Frontier
Mon, Jun 1 - Wed, Jun 3
Frontier Logo
9:55 pm - 2:12 pm
MSY
-
MDW
16h 17m
2 stops
Frontier Logo
6:00 am - 4:21 pm
MDW
-
MSY
10h 21m
1 stop
$208Frontier
Thu, May 14 - Sat, May 16
Frontier Logo
4:25 pm - 3:57 pm
MSY
-
MDW
23h 32m
1 stop
Frontier Logo
6:00 am - 4:21 pm
MDW
-
MSY
10h 21m
1 stop
$212Frontier
Fri, May 22 - Tue, May 26
Frontier Logo
5:21 pm - 10:02 pm
MSY
-
MDW
28h 41m
1 stop
Frontier Logo
6:00 am - 4:21 pm
MDW
-
MSY
10h 21m
1 stop
$213Frontier
Sat, May 30 - Mon, Jun 1
Frontier Logo
5:21 pm - 11:12 am
MSY
-
MDW
17h 51m
1 stop
Frontier Logo
6:00 am - 4:21 pm
MDW
-
MSY
10h 21m
1 stop
$216Frontier
Wed, May 27 - Sun, May 31
Frontier Logo
5:21 pm - 11:12 am
MSY
-
MDW
17h 51m
1 stop
Frontier Logo
6:00 am - 4:21 pm
MDW
-
MSY
10h 21m
1 stop
$220Frontier
Fri, May 22 - Tue, May 26
Multiple Airlines Logo
5:29 pm - 10:02 pm
MSY
-
MDW
28h 33m
2 stops
Multiple Airlines Logo
6:00 am - 4:21 pm
MDW
-
MSY
10h 21m
1 stop
$222Multiple Airlines
Tue, May 26 - Sat, May 30
Frontier Logo
5:21 pm - 11:09 am
MSY
-
MDW
17h 48m
1 stop
Frontier Logo
6:00 am - 4:21 pm
MDW
-
MSY
10h 21m
1 stop
$223Frontier
Thu, May 14 - Sun, May 17
Frontier Logo
4:25 pm - 3:57 pm
MSY
-
MDW
23h 32m
1 stop
Frontier Logo
6:00 am - 4:26 pm
MDW
-
MSY
10h 26m
1 stop
$224Frontier
Booking Insights

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

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

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

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

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

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

If you are looking for a flight deal from New Orleans to Chicago Midway Airport, look for departures on Thursdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Saturday is the cheapest day to fly and Friday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from New Orleans to Chicago Midway Airport, 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 New Orleans to Chicago Midway Airport is June, where tickets cost $227 (return) on average. On the other hand, the most expensive months are May and July, where the average cost of round-trip tickets is $372 and $358 respectively.

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

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $247 on average.

Expert advice

Expert advice for your flight from New Orleans to Midway

 
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 seasonJanuary
Cheapest flight$99
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 21% lower on average.
Flight from New Orleans to Chicago Midway Airport

When to book flights from New Orleans to Midway

Are your dates flexible? Find out the best times to travel from New Orleans to Midway 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 New Orleans to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from New Orleans to Chicago Midway Airport was $99 for a one-way ticket and $201 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

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

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

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the New Orleans to Chicago Midway Airport flight route.

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

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

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

    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 New Orleans to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from New Orleans 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 New Orleans to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to New Orleans with another airline. Booking your flights between New Orleans and MDW 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 New Orleans to Chicago Midway Airport?

    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 Chicago Midway Airport from New Orleans 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 New Orleans to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $179 or less one-way and $292 or less round-trip.

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

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

Direct departures

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

Direct returns

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

Reviews of the top airline flying from New Orleans to Midway

 
See real verified KAYAK customer reviews for airlines flying from New Orleans to Chicago. 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 New Orleans to Midway? 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 4314 reviews
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

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

Information on your arrival and departure airports