Southwest offers free messaging and affordable Wi-Fi for a connected flight experience.
Southwest's open seating policy allows flexible seat choice, enhancing boarding efficiency.

Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $114 (Kiwi.com) |
One-way from | $81 (Expedia) |
Popular in | December |
Cheapest in | August |
Average price | $296 |
Good round-trip deal | $296 or less |
Good one-way deal | $177 or less |
Fly from
Fly to
Route
Depart
Return
Price
New OrleansChicago
MSY - ORD
MSYORD
New Orleans Louis Armstrong
Fri 1/16
9:17 am-11:47 am
Nonstop2h 30m
Chicago O'Hare Intl
Mon 1/19
8:43 pm-8:21 am
1 stop11h 38m
New OrleansChicago
MSY - ORD
MSYORD
New Orleans Louis Armstrong
Fri 1/16
4:14 pm-12:08 pm
1 stop19h 54m
Chicago O'Hare Intl
Mon 1/19
8:43 pm-9:29 pm
1 stop24h 46m
New OrleansChicago
MSY - ORD
MSYORD
New Orleans Louis Armstrong
Fri 1/16
4:14 pm-12:08 pm
1 stop19h 54m
Chicago O'Hare Intl
Sun 1/18
8:43 pm-8:21 am
1 stop11h 38m
New OrleansChicago
MSY - ORD
MSYORD
New Orleans Louis Armstrong
Tue 4/21
11:06 am-11:12 pm
1 stop12h 06m
Chicago O'Hare Intl
Wed 4/22
7:35 pm-10:08 pm
Nonstop2h 33m
New OrleansChicago
MSY - ORD
MSYORD
New Orleans Louis Armstrong
Wed 1/7
6:40 am-7:02 pm
2 stops12h 22m
Chicago O'Hare Intl
Fri 1/9
8:43 pm-8:21 am
1 stop11h 38m
New OrleansChicago
MSY - ORD
MSYORD
New Orleans Louis Armstrong
Thu 1/15
8:36 pm-11:22 am
2 stops14h 46m
Chicago O'Hare Intl
Mon 1/19
8:43 pm-9:29 pm
1 stop24h 46m
New OrleansChicago
MSY - MDW
MSYMDW
New Orleans Louis Armstrong
Wed 1/14
3:31 pm-10:07 pm
1 stop6h 36m
Chicago Midway
Tue 1/20
10:48 am-4:20 pm
1 stop5h 32m
New OrleansChicago
MSY - MDW
MSYMDW
New Orleans Louis Armstrong
Thu 1/15
6:35 am-8:55 am
Nonstop2h 20m
Chicago Midway
Mon 1/19
8:40 pm-11:05 pm
Nonstop2h 25m
New OrleansChicago
MSY - MDW
MSYMDW
New Orleans Louis Armstrong
Sun 1/25
6:35 am-8:55 am
Nonstop2h 20m
Chicago Midway
Tue 1/27
7:50 pm-10:15 pm
Nonstop2h 25m
New OrleansChicago
MSY - MDW
MSYMDW
New Orleans Louis Armstrong
Thu 1/15
6:35 am-8:55 am
Nonstop2h 20m
Chicago Midway
Thu 1/22
7:50 pm-10:15 pm
Nonstop2h 25m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
The price you pay for your flight from New Orleans to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 71 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, February is the cheapest month in which you can book a flight from New Orleans to Chicago (average of $57). Flying from New Orleans to Chicago in January is currently the most expensive (average of $174). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
When flying from New Orleans to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 64% versus a flight at noon.
Travelers seeking maximum savings on their New Orleans to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Entertainment
Food
Boarding
Comfort
Crew
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Food
Boarding
Comfort
Crew
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Food
Boarding
Comfort
Crew
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Food
Boarding
Comfort
Crew
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Food
Boarding
Comfort
Crew
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Food
Boarding
Comfort
Crew
Overall
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$64 | Average$141 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$138 | Average$285 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$162 | Average$271 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$172 | Average$276 | FlexibilityNo cancel fee | On-time63% |