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 | $112 (Priceline) |
One-way from | $73 (Trip.com) |
Popular in | December |
Cheapest in | August |
Average price | $218 |
Good round-trip deal | $243 or less |
Good one-way deal | $158 or less |
Fly from
Fly to
Route
Depart
Return
Price
New OrleansChicago
MSY - MDW
MSYMDW
New Orleans Louis Armstrong
Thu 12/11
4:35 pm-10:12 pm
1 stop5h 37m
Chicago Midway
Mon 12/15
6:15 am-4:27 pm
1 stop10h 12m
New OrleansChicago
MSY - ORD
MSYORD
New Orleans Louis Armstrong
Thu 12/11
10:35 am-1:10 pm
Nonstop2h 35m
Chicago O'Hare Intl
Mon 12/15
7:45 pm-10:21 pm
Nonstop2h 36m
New OrleansChicago
MSY - MDW
MSYMDW
New Orleans Louis Armstrong
Sat 12/13
6:30 am-8:50 am
Nonstop2h 20m
Chicago Midway
Mon 12/15
8:20 pm-10:40 pm
Nonstop2h 20m
New OrleansChicago
MSY - MDW
MSYMDW
New Orleans Louis Armstrong
Thu 1/15
6:25 am-8:45 am
Nonstop2h 20m
Chicago Midway
Mon 1/19
7:40 am-10:05 am
Nonstop2h 25m
New OrleansChicago
MSY - MDW
MSYMDW
New Orleans Louis Armstrong
Thu 12/11
6:20 am-8:40 am
Nonstop2h 20m
Chicago Midway
Mon 12/15
8:20 pm-10:40 pm
Nonstop2h 20m
New OrleansChicago
MSY - ORD
MSYORD
New Orleans Louis Armstrong
Wed 11/26
9:48 am-12:08 pm
Nonstop2h 20m
Chicago O'Hare Intl
Mon 12/1
1:03 pm-3:24 pm
Nonstop2h 21m
New OrleansChicago
MSY - ORD
MSYORD
New Orleans Louis Armstrong
Mon 11/24
12:14 pm-5:32 am
1 stop17h 18m
Chicago O'Hare Intl
Wed 11/26
6:35 pm-10:15 am
1 stop15h 40m
New OrleansChicago
MSY - MDW
MSYMDW
New Orleans Louis Armstrong
Sat 12/13
5:15 am-9:54 am
1 stop4h 39m
Chicago Midway
Tue 12/16
12:50 pm-6:04 pm
1 stop5h 14m
New OrleansChicago
MSY - MDW
MSYMDW
New Orleans Louis Armstrong
Wed 12/10
9:24 am-4:34 pm
1 stop7h 10m
Chicago Midway
Sat 12/13
6:00 am-12:01 pm
1 stop6h 01m
New OrleansChicago
MSY - MDW
MSYMDW
New Orleans Louis Armstrong
Sat 2/28
11:18 am-6:34 pm
1 stop7h 16m
Chicago Midway
Tue 3/3
6:00 am-10:27 am
1 stop4h 27m
| 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 Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars |
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, March is the cheapest month in which you can book a flight from New Orleans to Chicago (average of $58). Flying from New Orleans to Chicago in January is currently the most expensive (average of $168). 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 62% 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.
Comfort
Entertainment
Food
Overall
Crew
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Entertainment
Food
Overall
Crew
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Entertainment
Food
Overall
Crew
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Entertainment
Food
Overall
Crew
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Entertainment
Food
Overall
Crew
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Entertainment
Food
Overall
Crew
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$67 | Average$185 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$140 | Average$303 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$163 | Average$282 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$185 | Average$285 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$216 | Average$287 | FlexibilityNo cancel fee | On-timeN/A |