MSY - MDW

$79 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 8/4. 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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Flights 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

Thu, Aug 7 - Tue, Aug 12
Southwest Logo
5:20 pm - 7:35 pmMSY-MDW
2h 15mnonstop
Southwest Logo
7:20 pm - 9:30 pmMDW-MSY
2h 10mnonstop
$157Southwest
Find Deal
Sat, Aug 9 - Mon, Aug 11
Southwest Logo
6:25 am - 8:40 amMSY-MDW
2h 15mnonstop
Southwest Logo
8:00 pm - 10:10 pmMDW-MSY
2h 10mnonstop
$160Southwest
Find Deal
Tue, Oct 21 - Wed, Oct 22
Southwest Logo
5:00 pm - 10:00 pmMSY-MDW
5h 00m1 stop
Southwest Logo
12:35 pm - 2:50 pmMDW-MSY
2h 15mnonstop
$163Southwest
Find Deal
Thu, Aug 7 - Tue, Aug 12
Southwest Logo
6:30 am - 8:45 amMSY-MDW
2h 15mnonstop
Southwest Logo
9:00 am - 3:40 pmMDW-MSY
6h 40m1 stop
$167Southwest
Find Deal
Sat, Jul 26 - Tue, Jul 29
Delta Logo
5:25 am - 9:45 amMSY-MDW
4h 20m1 stop
Delta Logo
9:25 am - 4:36 pmMDW-MSY
7h 11m1 stop
$217Delta
Find Deal
Mon, Sep 8 - Fri, Sep 12
Frontier Logo
4:51 pm - 11:25 pmMSY-MDW
6h 34m1 stop
Frontier Logo
8:15 am - 8:33 pmMDW-MSY
12h 18m1 stop
$218Frontier
Find Deal
Thu, Sep 4 - Thu, Sep 11
Frontier Logo
4:51 pm - 11:25 pmMSY-MDW
6h 34m1 stop
Frontier Logo
6:15 am - 3:56 pmMDW-MSY
9h 41m1 stop
$226Frontier
Find Deal
Tue, Jul 1 - Tue, Jul 15
Delta Logo
2:54 pm - 9:45 pmMSY-MDW
6h 51m1 stop
Delta Logo
9:24 am - 3:21 pmMDW-MSY
5h 57m1 stop
$233Delta
Find Deal
Thu, Jul 31 - Mon, Aug 4
 Logo
8:15 pm - 1:56 pmMSY-MDW
17h 41m2 stops
 Logo
1:11 pm - 11:43 amMDW-MSY
22h 32m2 stops
Thu, Jun 26 - Mon, Jun 30
 Logo
6:21 am - 2:03 pmMSY-MDW
31h 42m3 stops
 Logo
10:34 am - 6:09 amMDW-MSY
19h 35m2 stops
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
Useful Info

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.

Good to know

Low seasonJanuary
High seasonJune
Cheapest flight$79
Best time to beat the crowds with an average 0% drop 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 $79 for a one-way ticket and $157 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, Delta, and JetBlue 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 $291 and an overall rating of 8.0.

  • 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 $138 or less one-way and $211 or less round-trip.

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

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
See more direct flights

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 4287 reviews
8.6Crew
8.2Boarding
8.0Comfort
7.1Food
7.6Entertainment
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

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

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

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.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

The flight was rescheduled several times without a reason for the schedule changes. I had to be in New Orleans at a certain time and it was just easier to drive at a certain point. I don’t know if the flight ever left. This is my first experience with Spirit Airlines and is also the last.

In a word, it was horrible. The flight crew timed out and this, apparently was not accounted for by management. This meant that our 10:15 departure turned into a 1:30am departure the next DAY!!! And some brainchild decided to email us 12$ food vouchers set to expire the 9th, but they sent them after EVERY VENDOR WAS CLOSED in the Miami airport and obviously none would be open in New Orleans. I found this to be another sterling example of, at best, shitty management…at worst an absolute lack of empathy for your customers. Triplt Pro: Check-in may be avail for NK222 dep MIA 4/8/2025 10:16pm. Conf#RGSUMI. https://tripit.com/t/. e106fd644e0a; Today 6:16 PM TripIt Pro: NK222 ON TIME. MIA dep 10:16pm term C, gate F5. MSY arr 11:38pm. Today 8:59 PM Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 2:18am. Alternate flights: https:// www.tripit.com/t/b2903869f438 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/834d176c630b Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/0441e41a9dd3 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:// www.tripit.com/t/92ac2157ef54 The sender is not in your contact

My only complaint is that the standing recline. I wasn’t aware of that when I booked the ticket.

A passenger got into a verbal altercation with the flight attendant, who neither de-escalated nor acted professionally. Because of this, we had to go back to the gate for the person to be kicked off the flight. It delayed us 75 minutes.

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

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