MSY - CHI

$79 Find Cheap Southwest Flights from New Orleans to Chicago

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Cheap Southwest Flight Deals from New Orleans to Chicago

 
Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from New Orleans to Chicago 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 Southwest flight deals from New Orleans to Chicago

Wed, Nov 12 - Sat, Nov 15
Southwest Logo
6:20 am - 8:40 amMSY-MDW
2h 20mnonstop
Southwest Logo
4:30 pm - 6:50 pmMDW-MSY
2h 20mnonstop
$157Southwest
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Fri, Dec 12 - Tue, Dec 16
Southwest Logo
6:25 pm - 8:40 pmMSY-MDW
2h 15mnonstop
Southwest Logo
8:20 pm - 10:40 pmMDW-MSY
2h 20mnonstop
$163Southwest
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Fri, Nov 14 - Sun, Nov 16
Southwest Logo
6:25 pm - 8:40 pmMSY-MDW
2h 15mnonstop
Southwest Logo
4:15 pm - 6:35 pmMDW-MSY
2h 20mnonstop
$169Southwest
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Sat, Nov 8 - Sun, Nov 9
Southwest Logo
6:30 am - 8:50 amMSY-MDW
2h 20mnonstop
Southwest Logo
9:30 pm - 11:50 pmMDW-MSY
2h 20mnonstop
$173Southwest
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Thu, Oct 30 - Mon, Nov 3
Southwest Logo
10:40 am - 1:00 pmMSY-MDW
2h 20mnonstop
Southwest Logo
8:20 pm - 10:40 pmMDW-MSY
2h 20mnonstop
$179Southwest
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Thu, Oct 30 - Tue, Nov 4
Southwest Logo
2:30 pm - 7:40 pmMSY-MDW
5h 10m1 stop
Southwest Logo
8:20 pm - 10:40 pmMDW-MSY
2h 20mnonstop
$183Southwest
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Wed, Oct 29 - Sun, Nov 2
Southwest Logo
6:40 am - 9:00 amMSY-MDW
2h 20mnonstop
Southwest Logo
8:00 am - 10:25 amMDW-MSY
2h 25mnonstop
$184Southwest
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Thu, Oct 30 - Mon, Nov 3
Southwest Logo
6:05 am - 8:25 amMSY-MDW
2h 20mnonstop
Southwest Logo
8:20 pm - 10:40 pmMDW-MSY
2h 20mnonstop
$189Southwest
Find Deal
Sat, Nov 1 - Mon, Nov 3
Southwest Logo
2:20 pm - 4:40 pmMSY-MDW
2h 20mnonstop
Southwest Logo
3:30 pm - 9:20 pmMDW-MSY
5h 50m1 stop
$194Southwest
Find Deal
Wed, Oct 29 - Sun, Nov 2
Southwest Logo
5:00 pm - 10:00 pmMSY-MDW
5h 00m1 stop
Southwest Logo
8:00 am - 10:25 amMDW-MSY
2h 25mnonstop
$195Southwest
Find Deal
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Good to know

Low seasonJanuary
Cheapest flight$79
Average price round-trip$214
Good deal one-way$168
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from New Orleans to Chicago Midway Airport
(avg. price over the last 2 weeks)
or less

When to Book Flights with Southwest from New Orleans to Chicago

Average price per month
Flight prices as travel date approaches

FAQs for flying to Chicago with Southwest

  • How far in advance should I book tickets for a flight with Southwest from New Orleans to Chicago?

    Generally, when trying to get a below average price for your ticket, try to book around 7 days before departure. For the cheapest possible price, our data suggests booking 63 days before departure.

  • Is Southwest the cheapest airline to fly with from New Orleans to Chicago?

    With an average price of $287 return, Southwest is not the cheapest airline to fly from New Orleans to Chicago with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $186 on average.

  • What is the cheapest Southwest flight from New Orleans to Chicago?

    In the last 3 days, the lowest price for a flight with Southwest from New Orleans to Chicago was $109 for a return flight and $65 for a one-way flight.

  • Does Southwest fly direct to Chicago from New Orleans?

    Yes, Southwest does offer direct flights for the route, with around 19 flights per week.

  • What’s the cheapest day of the week to fly from New Orleans to Chicago with Southwest?

    On average, the cheapest day of the week to fly from New Orleans to Chicago with Southwest is Tuesday, when prices are around $74. The most expensive day is generally Saturday, where the average price is around $118.

  • What’s the cheapest month to fly from New Orleans to Chicago with Southwest?

    The cheapest month for Southwest flights to Chicago from New Orleans is generally August, where plane tickets cost $163 on average. If possible, try to avoid the most expensive months of January and February, where tickets cost $416 and $428 respectively.

Southwest Customer Reviews

8.0
Very good4,235 verified ratings
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Pros +
Cons -
Show reviews that mention
Traveler rating:
Sort by:
A
8.0 Very good
MCI-LGA
Good non stop is always good
G
10.0 Wonderful
DEN-SMF
Connecting flight is on time and boarding was a breeze!
G
10.0 Wonderful
LGA-DEN
Easy boarding process. No delays!
M
10.0 Wonderful
MDW-DTW
Excellent
M
10.0 Wonderful
MSY-MDW
Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience
R
10.0 Wonderful
RNO-LAS
As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.
A
4.0 Mediocre
PHX-OGG
Southwest airlines boarding process is the worst. Period.
V
8.0 Very good
LAS-DTW
Good
V
10.0 Wonderful
CLT-BWI
Always liked SW
L
10.0 Wonderful
MDW-OKC
Clear communication

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

Cabin class types available on flights to Chicago

Cabin classes available on flights to New Orleans. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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