MSY - MDW

$67 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 10/21. 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

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
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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

Fri, Oct 24 - Sun, Oct 26
Frontier Logo
6:06 pm - 11:46 pmMSY-MDW
5h 40m1 stop
Frontier Logo
6:20 am - 4:37 pmMDW-MSY
10h 17m1 stop
$119Frontier
Find Deal
Thu, Oct 2 - Mon, Oct 6
Frontier Logo
4:51 pm - 11:41 pmMSY-MDW
6h 50m1 stop
Frontier Logo
6:20 am - 3:57 pmMDW-MSY
9h 37m1 stop
$122Frontier
Find Deal
Thu, Oct 2 - Sat, Oct 11
 Logo
4:51 pm - 11:41 pmMSY-MDW
6h 50m1 stop
 Logo
10:00 am - 9:12 pmMDW-MSY
11h 12m1 stop
Sat, Oct 4 - Mon, Oct 6
 Logo
10:01 pm - 12:46 pmMSY-MDW
14h 45m1 stop
 Logo
6:20 am - 3:57 pmMDW-MSY
9h 37m1 stop
Mon, Oct 27 - Thu, Oct 30
 Logo
6:05 pm - 11:38 amMSY-MDW
17h 33m1 stop
 Logo
6:20 am - 6:59 pmMDW-MSY
12h 39m1 stop
Fri, Oct 24 - Fri, Oct 31
Frontier Logo
6:06 pm - 11:46 pmMSY-MDW
5h 40m1 stop
Frontier Logo
9:15 am - 3:19 pmMDW-MSY
6h 04m1 stop
$138Frontier
Find Deal
Sat, Nov 1 - Tue, Nov 4
Southwest Logo
6:30 am - 8:50 amMSY-MDW
2h 20mnonstop
Southwest Logo
8:20 pm - 10:40 pmMDW-MSY
2h 20mnonstop
$145Southwest
Find Deal
Sat, Oct 11 - Sun, Oct 12
Southwest Logo
11:10 am - 1:30 pmMSY-MDW
2h 20mnonstop
Southwest Logo
10:40 pm - 12:55 amMDW-MSY
2h 15mnonstop
$149Southwest
Find Deal
Thu, Dec 4 - Tue, Dec 9
Southwest Logo
6:20 am - 8:40 amMSY-MDW
2h 20mnonstop
Southwest Logo
8:20 pm - 10:40 pmMDW-MSY
2h 20mnonstop
$151Southwest
Find Deal
Fri, Nov 14 - Mon, Nov 17
Southwest Logo
6:20 am - 8:40 amMSY-MDW
2h 20mnonstop
Southwest Logo
8:40 am - 11:05 amMDW-MSY
2h 25mnonstop
$156Southwest
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
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
Frontier
Cheapest • from $119 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 56% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 30% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$119
Overall average: $310
Frontier
Fri 10/24Sun 10/26
MSY - MDW • 1 stop
Cheapest non-stop
$133
Typical prices: $300-564
Southwest
Sat 11/1Tue 11/4
MSY - MDW • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Expert advice

Expert advice for your flight from New Orleans to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-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.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
MSY

MSY offers free Wi-Fi throughout the airport, making it easy to stay connected before your flight.

Read more about MSYby Daniel Scheffler
MDW

Take the CTA Orange Line from MDW to downtown Chicago in about 25-30 minutes, avoiding traffic hassles.

Read more about MDWby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

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.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on MSY

Daniel Scheffler

Daniel Scheffler

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.

Read more
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.

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, Tuesday is the cheapest day to fly and Thursday 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 February, where tickets cost $198 (return) on average. On the other hand, the most expensive months are December and August, where the average cost of round-trip tickets is $359 and $323 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from New Orleans to Chicago Midway Airport, you should book around 3 weeks before departure, which saves you about 56% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$67
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 20% 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 $67 for a one-way ticket and $119 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, Delta, Hawaiian Airlines, and Alaska 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 737-800 Passenger/BBJ2 (winglets) 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.

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

    The two airlines most popular with KAYAK users for flights from New Orleans to Chicago are Southwest and Delta. With an average price for the route of $289 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $287 and an overall rating of 7.9.

  • 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 $148 or less one-way and $207 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 3 airlines serving 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 4248 reviews
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

Flight was 2hours late they had no crew or the pilot.

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

Information on your arrival and departure airports

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