MDW - MSY

$144 Find Cheap Flights from Chicago Midway Airport to New Orleans - Compare and Save

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Everything you should know

Cheapest round-trip
$280
Typical prices: $305-$488
Frontier
Mon 11/19Fri 11/23
MDW - MSY • 1 stop
Cheapest non-stop
$285
Typical prices: $313-$492
Southwest
Wed 12/12Wed 12/19
MDW - MSY • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 22m
Direct flights
+1
Direct flights
+1
Avoid delays
Most punctual • 80% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 9 weeks in advance save around 43% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 26% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $268 (round-trip)
Shortest trip • 4h 16m (one-way)
Insights
Insights
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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)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to New Orleans

Thu, Nov 19 - Mon, Nov 23
Frontier Logo
6:08 am - 5:14 pmMDW  Chicago Midway-MSY New Orleans Louis Armstrong
11h 06m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:55 pm - 7:47 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
24h 52m1 stop Orlando
$280Frontier
Wed, Nov 11 - Fri, Nov 13
Frontier Logo
6:08 am - 3:47 pmMDW  Chicago Midway-MSY New Orleans Louis Armstrong
9h 39m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
4:42 pm - 11:47 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
7h 05m1 stop Atlanta Hartsfield-Jackson
$280Frontier
Thu, Dec 3 - Mon, Dec 7
Frontier Logo
5:02 pm - 8:38 amMDW  Chicago Midway-MSY New Orleans Louis Armstrong
15h 36m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:05 pm - 11:33 amMSY  New Orleans Louis Armstrong-MDW Chicago Midway
41h 28m2 stops Orlando Atlanta Hartsfield-Jackson
$280Frontier
Thu, Jan 7 - Sun, Jan 10
Frontier Logo
8:30 pm - 4:49 pmMDW  Chicago Midway-MSY New Orleans Louis Armstrong
20h 19m1 stop Orlando
Frontier Logo
11:35 am - 4:26 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
4h 51m1 stop Atlanta Hartsfield-Jackson
$281Frontier
Sat, Dec 12 - Mon, Dec 14
Southwest Logo
7:55 am - 3:15 pmMDW  Chicago Midway-MSY New Orleans Louis Armstrong
7h 20m2 stops Louisville Intl Orlando
Southwest Logo
6:00 am - 12:15 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
6h 15m1 stop Denver Intl
$284Southwest
Sat, Dec 5 - Wed, Dec 9
Southwest Logo
8:00 am - 3:25 pmMDW  Chicago Midway-MSY New Orleans Louis Armstrong
7h 25m2 stops Detroit Metropolitan Wayne County Nashville Intl
Southwest Logo
6:00 am - 12:15 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
6h 15m1 stop Denver Intl
$284Southwest
Sat, Dec 12 - Mon, Dec 14
Southwest Logo
8:00 am - 3:25 pmMDW  Chicago Midway-MSY New Orleans Louis Armstrong
7h 25m2 stops Detroit Metropolitan Wayne County Nashville Intl
Southwest Logo
7:20 am - 12:20 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
5h 00m1 stop Dallas Love Field
$284Southwest
Tue, Nov 10 - Sat, Nov 14
Multiple Airlines Logo
6:42 pm - 3:47 pmMDW  Chicago Midway-MSY New Orleans Louis Armstrong
21h 05m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
9:10 am - 11:47 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
14h 37m2 stops Raleigh-Durham Atlanta Hartsfield-Jackson
$285Multiple Airlines
Wed, Jan 13 - Mon, Jan 18
Multiple Airlines Logo
6:01 am - 9:03 amMDW  Chicago Midway-MSY New Orleans Louis Armstrong
27h 02m1 stop Dallas/Fort Worth
Multiple Airlines Logo
2:35 pm - 11:46 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
9h 11m2 stops Orlando Atlanta Hartsfield-Jackson
$293Multiple Airlines
Wed, Jan 13 - Mon, Jan 18
Multiple Airlines Logo
6:01 am - 9:03 amMDW  Chicago Midway-MSY New Orleans Louis Armstrong
27h 02m1 stop Dallas/Fort Worth
Multiple Airlines Logo
2:35 pm - 11:46 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
9h 11m2 stops Orlando Atlanta Hartsfield-Jackson
$294Multiple Airlines
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to New Orleans flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

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

Round-trip flights from Chicago Midway Airport to New Orleans typically range from $305 to $488. The lowest price found in the past 5 days was $280, on Frontier.

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

Based on deals KAYAK users found in the last 12 months, Monday is the cheapest day of the week to fly from Chicago Midway Airport to New Orleans. It’s 12% cheaper than the average day, while Thursday is the most expensive, with prices 11% higher.

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

•January is the cheapest month to fly from Chicago Midway Airport to New Orleans at $290 round-trip.
•April ($438) and November ($437) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 51% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago Midway Airport to New Orleans the cheapest?

Flights from Chicago Midway Airport to New Orleans are cheapest 9 weeks before departure. Booking in this window typically costs about 43% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Midway to New Orleans

 
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.

Key details for Chicago Midway Airport to New Orleans flights

Low season

August

Cheapest flight

$145
Beat the crowds with an average 39% drop in travelers.
The most popular month to fly with an average 34% increase in travelers.
One-way 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

Your Chicago Midway Airport to New Orleans flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Chicago Midway Airport to New Orleans?

    These are the earliest and latest flight times available from Chicago Midway Airport to New Orleans:

    • Earliest: departs at 5:00 am and lands at 7:22 am
    • Latest: departs at 10:25 pm and lands at 12:47 am.

    The flight takes about 2h 22m.

  • What cabin classes can I book on flights from Chicago Midway Airport to New Orleans?

    Only Economy Class is available on flights from Chicago Midway Airport to New Orleans.

  • How long is a flight from Chicago Midway Airport to New Orleans?

    A nonstop flight from Chicago Midway Airport to New Orleans takes 2h 22m, covering 827 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Chicago Midway Airport to New Orleans flight?

    Round-trip flights from Chicago Midway Airport to New Orleans range from $305 to $488, with an average of $394 over the past 12 months. Anything below $305 counts as a good deal.

  • How expensive are last-minute Chicago Midway Airport to New Orleans flights?

    Last-minute fares on this route (booked within two weeks of departure) run 41% above the $394 route average. Book 9 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Chicago Midway Airport to New Orleans?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $268 round-trip via Denver Intl (DEN), compared to $397 for nonstop.

  • How does on-time performance compare across airlines flying from Chicago Midway Airport to New Orleans?

    Southwest is the only airline operating Chicago Midway Airport to New Orleans flights. 80% of its flights are on time.

  • What is the standard checked-bag allowance on flights from Chicago Midway Airport to New Orleans?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Chicago Midway Airport to New Orleans?

    The Airbus A320-100/200 family is used most often on this route, operated mainly by United Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

  • How are flight departures from Chicago Midway Airport to New Orleans spread across the day?

    Morning is the busiest departure period on Chicago Midway Airport to New Orleans flights, with 34% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 33%, and night flights for 0%.

  • Which airlines offer Wi-Fi on Chicago Midway Airport to New Orleans flights?

    JetBlue is the only airline on the Chicago Midway Airport to New Orleans route offering in-flight Wi-Fi. Pricing depends on fare class.

  • How are flight prices from Chicago Midway Airport to New Orleans looking right now?

    One-way fares from Chicago Midway Airport to New Orleans are currently lower than usual. Average one-way flight prices are about $153, which is 26% below the typical average for this route.

  • What car rental options are available at New Orleans Louis Armstrong Airport (MSY)?

    New Orleans Louis Armstrong Airport (MSY) hosts 5 major car rental companies, with daily rates averaging $62 for economy cars. Top options include:

    • Dollar
    • Hertz
    • Priceless
    • Thrifty
    • Budget

  • Which airports can I use when flying from Chicago Midway Airport to New Orleans?

    Flights from Chicago Midway Airport to New Orleans usually depart from Chicago Midway (MDW) and arrive at New Orleans Louis Armstrong (MSY).

  • What time of day has the fewest delays on flights from Chicago Midway Airport to New Orleans?

    Morning flights have the fewest delays on this route, while night departures tend to have the most.

  • At what point is a flight considered delayed from Chicago Midway Airport to New Orleans?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago Midway Airport to New Orleans route, 20% of flights were delayed in the past 3 months, with delays averaging 1h 57m.

  • Which airports do connecting flights from Chicago Midway Airport to New Orleans pass through?

    One-stop flights from Chicago Midway Airport to New Orleans most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 58% of one-stop connections
    • Houston Hobby (HOU) - 23% of one-stop connections
    • Lambert-St Louis (STL) - 13% of one-stop connections
    • Denver Intl (DEN) - 3% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to New Orleans?

    Yes. Flexible dates can save you up to 21% on flights from Chicago Midway Airport to New Orleans. Monday is the cheapest departure day at $349 round-trip on average, while Thursday is the most expensive at $438, a difference of $89.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Chicago Midway Airport to New Orleans?

    Only Southwest operates flights between Chicago Midway Airport and New Orleans.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to New Orleans?

    Flying via Lambert-St Louis (STL) gives the shortest average 1-stop total travel time at 4h 16m, compared with 4h 45m via Houston Hobby (HOU) and 6h 02m via Denver Intl (DEN).

  • What popular places can I visit in New Orleans?

    Some of the most popular sights in New Orleans are New Orleans Morial Convention Center, Caesars Superdome and Canal Street. These are among the most viewed places in New Orleans on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Chicago Midway Airport to New Orleans flights?

    Among airlines operating Chicago Midway Airport to New Orleans flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Chicago Midway Airport to New Orleans flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Chicago Midway Airport to New Orleans flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Monday departure and avoid flying on Thursday. On this route, Monday flights average $349, about $89 less than Thursday fares (20% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 9 weeks before you fly. On this route, that window historically saves about 43% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to New Orleans trip for January. Fares historically average $290 round-trip in that month - typically $148 less than the most expensive month, which is April (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Denver Intl Airport (DEN) can be cheaper than flying direct. The cheapest layover option averages $268 round-trip on this route - about $129 less than direct flights (based on the last 12 months).

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

 
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

More options for your flight from Midway to New Orleans

Complete your trip to New Orleans with a hotel stay or car rental