MSY - MDW

$148 Find Cheap Flights from New Orleans to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$286
Typical prices: $275-$450
Frontier
Sat 11/17Thu 11/22
MSY - MDW • 1 stop
Cheapest non-stop
$288
Typical prices: $281-$456
Southwest
Mon 12/17Fri 12/21
MSY - MDW • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 19m
Direct flights
+1
Direct flights
+1
When to book
in advance
Our data shows that travelers who book at least 7 weeks in advance save around 42% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 32% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $280 (round-trip)
Shortest trip • 3h 50m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Expert advice
Flight Deals

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

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

Recent round-trip flight deals from New Orleans to Midway

Tue, Nov 17 - Sun, Nov 22
Frontier Logo
5:08 pm - 11:47 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
6h 39m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:42 pm - 6:20 pmMDW  Chicago Midway-MSY New Orleans Louis Armstrong
45h 38m2 stops Orlando Dallas/Fort Worth
$286Frontier
Mon, Dec 21 - Mon, Jan 4
Frontier Logo
9:30 am - 7:30 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
10h 00m1 stop Orlando
Frontier Logo
8:35 pm - 10:50 amMDW  Chicago Midway-MSY New Orleans Louis Armstrong
38h 15m2 stops Orlando Atlanta Hartsfield-Jackson
$286Frontier
Fri, Nov 20 - Mon, Nov 23
Frontier Logo
6:55 pm - 7:47 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
24h 52m1 stop Orlando
Frontier Logo
8:42 pm - 6:00 pmMDW  Chicago Midway-MSY New Orleans Louis Armstrong
21h 18m1 stop Orlando
$287Frontier
Thu, Dec 17 - Mon, Dec 21
Southwest Logo
6:00 pm - 8:20 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
10:25 pm - 12:45 amMDW  Chicago Midway-MSY New Orleans Louis Armstrong
2h 20mnonstop
$288Southwest
Sun, Dec 20 - Mon, Dec 28
Frontier Logo
10:28 am - 12:03 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
25h 35m1 stop Dallas/Fort Worth
Frontier Logo
1:11 pm - 8:40 amMDW  Chicago Midway-MSY New Orleans Louis Armstrong
19h 29m1 stop Atlanta Hartsfield-Jackson
$288Frontier
Tue, Nov 24 - Fri, Nov 27
Southwest Logo
7:15 pm - 11:00 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
3h 45m1 stop Lambert-St Louis
Southwest Logo
9:20 pm - 11:50 pmMDW  Chicago Midway-MSY New Orleans Louis Armstrong
2h 30mnonstop
$289Southwest
Mon, Nov 23 - Thu, Nov 26
Frontier Logo
7:44 am - 12:21 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
4h 37m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
1:16 pm - 10:10 amMDW  Chicago Midway-MSY New Orleans Louis Armstrong
20h 54m2 stops Atlanta Hartsfield-Jackson Denver Intl
$289Frontier
Fri, Nov 20 - Mon, Nov 23
Frontier Logo
6:55 pm - 7:47 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
24h 52m1 stop Orlando
Frontier Logo
8:42 pm - 6:00 pmMDW  Chicago Midway-MSY New Orleans Louis Armstrong
21h 18m1 stop Orlando
$289Frontier
Fri, Nov 20 - Sun, Nov 22
Frontier Logo
6:55 pm - 7:47 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
24h 52m1 stop Orlando
Frontier Logo
8:42 pm - 6:00 pmMDW  Chicago Midway-MSY New Orleans Louis Armstrong
21h 18m1 stop Orlando
$289Frontier
Fri, Nov 27 - Tue, Dec 1
Southwest Logo
7:10 pm - 10:45 pmMSY  New Orleans Louis Armstrong-MDW Chicago Midway
3h 35m1 stop Lambert-St Louis
Southwest Logo
8:40 pm - 11:00 pmMDW  Chicago Midway-MSY New Orleans Louis Armstrong
2h 20mnonstop
$289Southwest
Booking Insights

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

Round-trip flights from New Orleans to Chicago Midway Airport typically range from $275 to $450. The lowest price found in the past 5 days was $286, on Frontier.

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

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from New Orleans to Chicago Midway Airport. It’s 17% cheaper than the average day, while Monday is the most expensive, with prices 34% higher.

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

•February is the cheapest month to fly from New Orleans to Chicago Midway Airport at $247 round-trip.
•June ($431) and November ($417) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 74% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

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

Flights from New Orleans to Chicago Midway Airport are cheapest 7 weeks before departure. Booking in this window typically costs about 42% 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 New Orleans to Midway

 
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 New Orleans to Chicago Midway Airport flights

Low season

January

Cheapest flight

$148
Beat the crowds with an average 59% drop in travelers.
The most popular month to fly with an average 76% increase in travelers.
One-way 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

Your New Orleans to Chicago Midway Airport 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 New Orleans to Chicago Midway Airport?

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

    • Earliest: departs at 5:05 am and lands at 7:24 am
    • Latest: departs at 6:10 pm and lands at 8:29 pm.

    The flight takes about 2h 19m.

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

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

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

    A nonstop flight from New Orleans to Chicago Midway Airport takes 2h 19m, covering 827 miles.

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

    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 New Orleans to Chicago Midway Airport flight?

    Round-trip flights from New Orleans to Chicago Midway Airport range from $275 to $450, with an average of $361 over the past 12 months. Anything below $275 counts as a good deal.

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

    Last-minute fares on this route (booked within two weeks of departure) run 35% above the $361 route average. Book 7 weeks before departure for the lowest fares.

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

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $280 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $366 for nonstop.

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

    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 New Orleans to Chicago Midway Airport?

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

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

    Morning is the busiest departure period on New Orleans to Chicago Midway Airport flights, with 50% of flights leaving in that window. Afternoon departures account for 50%, evening flights for 0%, and night flights for 0%.

  • Have flight prices from New Orleans to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $286 to $2,050. That means the highest observed fare was about 7x higher than the lowest one.

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

    One-way fares from New Orleans to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $151, which is 33% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

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

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

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

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

    • Atlanta Hartsfield-Jackson (ATL) - 91% of one-stop connections
    • Nashville Intl (BNA) - 4% of one-stop connections
    • Dallas Love Field (DAL) - 4% of one-stop connections

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

    Yes. Flexible dates can save you up to 39% on flights from New Orleans to Chicago Midway Airport. Tuesday is the cheapest departure day at $300 round-trip on average, while Monday is the most expensive at $486, a difference of $186.

    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 New Orleans to Chicago Midway Airport?

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

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

    Flying via Nashville Intl (BNA) gives the shortest average 1-stop total travel time at 3h 50m, compared with 5h 04m via Dallas Love Field (DAL) and 5h 51m via Atlanta Hartsfield-Jackson (ATL).

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

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

    Among airlines operating New Orleans to Chicago Midway Airport 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 New Orleans to Chicago Midway Airport 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

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

Your guide to booking New Orleans to Chicago Midway Airport 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 Tuesday departure and avoid flying on Monday. On this route, Tuesday flights average $300, about $186 less than Monday fares (38% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 7 weeks before you fly. On this route, that window historically saves about 42% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your New Orleans to Chicago Midway Airport trip for February. Fares historically average $247 round-trip in that month - typically $184 less than the most expensive month, which is June (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Atlanta Hartsfield-Jackson Airport (ATL) can be cheaper than flying direct. The cheapest layover option averages $280 round-trip on this route - about $85 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport

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

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

Direct returns

Chicago Midway to New Orleans Louis Armstrong

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

More options for your flight from New Orleans to Midway

Complete your trip to Chicago with a hotel stay or car rental