$59 Cheap Flights from New Orleans (MSY) to Chicago (MDW)

View $59 flight on Thu, Jan 29, 2026Opens in a new window

Popular airlines from Louis Armstrong New Orleans Intl. Airport (MSY) to Chicago Midway Airport (MDW)

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

Prices were available within the past 7 days and start at $59 for one-way flights and $118 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, Jan 6 - Sat, Jan 10
MSY
New Orleans
MDW
Chicago
$118 Roundtrip, found 9 hours ago
$118
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Tue, Jan 6 from New Orleans to Chicago, returning Sat, Jan 10, priced at $118 found 9 hours ago
Southwest Airlines
Wed, Dec 31 - Tue, Jan 6
MSY
New Orleans
MDW
Chicago
$138 Roundtrip, found 12 hours ago
$138
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Wed, Dec 31 from New Orleans to Chicago, returning Tue, Jan 6, priced at $138 found 12 hours ago
Frontier Airlines
Fri, Oct 24 - Mon, Oct 27
MSY
New Orleans
MDW
Chicago
$139 Roundtrip, found 10 hours ago
$139
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Fri, Oct 24 from New Orleans to Chicago, returning Mon, Oct 27, priced at $139 found 10 hours ago
Southwest Airlines
Wed, Dec 31 - Tue, Jan 6
MSY
New Orleans
MDW
Chicago
$148 Roundtrip, found 12 hours ago
$148
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Wed, Dec 31 from New Orleans to Chicago, returning Tue, Jan 6, priced at $148 found 12 hours ago
Southwest Airlines
Thu, Dec 11 - Sat, Jan 10
MSY
New Orleans
MDW
Chicago
$150 Roundtrip, found 12 hours ago
$150
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Thu, Dec 11 from New Orleans to Chicago, returning Sat, Jan 10, priced at $150 found 12 hours ago
Frontier Airlines
Thu, Oct 16 - Thu, Oct 30
MSY
New Orleans
MDW
Chicago
$154 Roundtrip, found 1 hour ago
$154
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Oct 16 from New Orleans to Chicago, returning Thu, Oct 30, priced at $154 found 1 hour ago
Southwest Airlines
Sat, Nov 8 - Tue, Nov 11
MSY
New Orleans
MDW
Chicago
$157 Roundtrip, found 1 hour ago
$157
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sat, Nov 8 from New Orleans to Chicago, returning Tue, Nov 11, priced at $157 found 1 hour ago
Frontier Airlines
Fri, Oct 31 - Sun, Nov 9
MSY
New Orleans
MDW
Chicago
$160 Roundtrip, found 12 hours ago
$160
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Fri, Oct 31 from New Orleans to Chicago, returning Sun, Nov 9, priced at $160 found 12 hours ago
Southwest Airlines
Thu, Nov 13 - Tue, Nov 18
MSY
New Orleans
MDW
Chicago
$163 Roundtrip, just found
$163
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Nov 13 from New Orleans to Chicago, returning Tue, Nov 18, priced at $163 just found
Delta
Thu, Dec 11 - Sat, Jan 10
MSY
New Orleans
MDW
Chicago
$173 Roundtrip, found 12 hours ago
$173
Roundtrip
found 12 hours ago
Select Delta flight, departing Thu, Dec 11 from New Orleans to Chicago, returning Sat, Jan 10, priced at $173 found 12 hours ago

Find the cheapest month to fly from New Orleans (MSY) to Chicago (MDW)

January is typically the cheapest month to fly

From $128 - $748 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $119
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $119
Flights from New Orleans (MSY) to Chicago (MDW)
Origin airport
Louis Armstrong New Orleans Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$118
Distance
827 mi
Average flight time
2 hours 46 mins

New Orleans to Chicago Flights

The cheapest times to fly from New Orleans to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from New Orleans to Chicago are during the month of January. You can find some of the cheapest flights from New Orleans to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from New Orleans to Chicago

Sunday is one of the best days to book for cheap flights from New Orleans to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from New Orleans to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from New Orleans to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $59 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap New Orleans to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your New Orleans to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Louis Armstrong New Orleans Intl. Airport (MSY) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $59 or cheap return flight from $118 from Louis Armstrong New Orleans Intl. Airport (MSY) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Louis Armstrong New Orleans Intl. Airport (MSY) to Midway Intl. Airport (MDW)?
The cheapest month to fly from MSY to MDW is January, when demand is low. Off-peak months are generally when better flight deals are available between these airports.
Which airlines fly direct from Louis Armstrong New Orleans Intl. Airport (MSY) to Midway Intl. Airport (MDW)?
Hop on a nonstop flight with Southwest Airlines and go straight from Louis Armstrong New Orleans Intl. Airport (MSY) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from Louis Armstrong New Orleans Intl. Airport (MSY) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from MSY to MDW, use Expedia's filter tool. Customize your search based on what's important to you, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from Louis Armstrong New Orleans Intl. Airport (MSY) to Midway Intl. Airport (MDW)?
Each day, an average of 2 direct flights operate from Louis Armstrong New Orleans Intl. Airport (MSY) to Midway Intl. Airport (MDW). Select the departure time that best suits your travel plans.
What are the most popular departure times for flights from Louis Armstrong New Orleans Intl. Airport (MSY) to Midway Intl. Airport (MDW)?
The 3 PM departures from MSY to MDW are typically the busiest. Greater demand means you'll likely pay more for these departures. If you want to save on your fare, pick a less crowded time to fly.
What day of the week has the most flights from MSY to MDW?
Depart on a Friday if you're after the best selection of flights from Louis Armstrong New Orleans Intl. Airport (MSY) to Midway Intl. Airport (MDW).
What is the earliest flight from Louis Armstrong New Orleans Intl. Airport (MSY) to Midway Intl. Airport (MDW)?
The earliest flight leaving from Louis Armstrong New Orleans Intl. Airport (MSY) is at around 6:40AM UTC-6. Board this flight and you'll reach Midway Intl. Airport (MDW) at approximately 9:00AM UTC-6. The total time in the air is 2h 20m.
How long does it take to fly from Louis Armstrong New Orleans Intl. Airport (MSY) to Midway Intl. Airport (MDW)?
Flights from MSY to MDW have an average travel time of 2 hours and 18 minutes. The total distance between the two is 830 mi.
What is the best time to fly from Louis Armstrong New Orleans Intl. Airport (MSY) to Midway Intl. Airport (MDW)?
Opt for a flight from Louis Armstrong New Orleans Intl. Airport (MSY) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the likelihood of delays and cancellations. Departures after this time have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Louis Armstrong New Orleans Intl. Airport (MSY)?
Take a direct flight from Louis Armstrong New Orleans Intl. Airport (MSY) to Chicago and touch down at O'Hare Intl. Airport (ORD). Another gateway to this city is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Louis Armstrong New Orleans Intl. Airport (MSY) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from MSY to MDW just before your getaway is generally more expensive. But if you're flexible with your departure times and dates, you could bag a cheap last-minute fare.
Is it cheaper to book a MSY to MDW flight and hotel package?
You'll generally save money by booking a MSY to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. Once you've chosen your ideal flights and accommodations, consider adding extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Louis Armstrong New Orleans Intl. Airport (MSY) to Midway Intl. Airport (MDW)?
Typically, you can cancel or modify your MSY to MDW flight. However, additional fees may apply, especially if you made your booking more than 24 hours ago. Double-check your itinerary for the airline's guidelines and fees on flight changes, or if you need further details, go to our Customer Service portal.

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*Available to One Key members.