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$67+ Cheap flights from New Orleans (MSY) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
MSY — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from New Orleans Louis Armstrong to Chicago are usually found in September or August, booked 76 days in advance, depart on a Friday or Thursday and return on a Monday

Cheap flight deals from New Orleans to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from New Orleans (MSY) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$117
(Cheapflightsfares)

One-way from

$67
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$170

Good round-trip deal

$185 or less

Good one-way deal

$135 or less
From New Orleans Louis Armstrong to Chicago (CHI)
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One-way flight from New Orleans Louis Armstrong to Chicago (CHI)
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Highest demand for flights based on searches. 15% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from New Orleans Louis Armstrong to Chicago (CHI).
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Price to beat on a one-way flight from New Orleans Louis Armstrong to Chicago (CHI).
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Find flight deals from New Orleans to Chicago

Cheapest flights from New Orleans to Chicago
Explore the most affordable flight options available from New Orleans to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/75:18 pmMSY - ORD
Nonstop2h 32mSpirit Airlines
Fri 10/109:48 amORD - MSY
Nonstop2h 26mSpirit Airlines
Deal found 9/10$117
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/68:38 pmMSY - ORD
Nonstop2h 27mSpirit Airlines
Sun 11/92:47 pmORD - MSY
Nonstop2h 23mSpirit Airlines
Deal found 9/10$119
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:06 pmMSY - MDW
1 stop5h 40mFrontier
Sun 10/266:20 amMDW - MSY
1 stop10h 17mFrontier
Deal found 9/9$119
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/168:00 pmMSY - ORD
Nonstop2h 26mSpirit Airlines
Tue 10/219:30 amORD - MSY
Nonstop2h 20mSpirit Airlines
Deal found 9/11$120
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/31:44 pmMSY - ORD
Nonstop2h 34mSpirit Airlines
Tue 10/149:30 amORD - MSY
Nonstop2h 20mSpirit Airlines
Deal found 9/9$121
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/24:51 pmMSY - MDW
1 stop6h 50mFrontier
Mon 10/66:20 amMDW - MSY
1 stop9h 37mFrontier
Deal found 9/9$122
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/145:18 pmMSY - ORD
Nonstop2h 32mSpirit Airlines
Mon 10/207:25 amORD - MSY
Nonstop2h 20mSpirit Airlines
Deal found 9/11$124
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/24:51 pmMSY - MDW
1 stop6h 50mMultiple Airlines
Sat 10/1110:00 amMDW - MSY
1 stop11h 12mMultiple Airlines
Deal found 9/9$124
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/115:18 pmMSY - ORD
Nonstop2h 32mSpirit Airlines
Thu 10/169:48 amORD - MSY
Nonstop2h 26mSpirit Airlines
Deal found 9/11$125
This Gotogate deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/115:18 pmMSY - ORD
Nonstop2h 32mMultiple Airlines
Sun 10/126:50 amORD - MSY
1 stop6h 26mMultiple Airlines
Deal found 9/10$127
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/21:44 pmMSY - ORD
Nonstop2h 34mSpirit Airlines
Thu 10/99:48 amORD - MSY
Nonstop2h 26mSpirit Airlines
Deal found 9/10$128
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/251:44 pmMSY - ORD
Nonstop2h 34mSpirit Airlines
Sun 9/2810:23 amORD - MSY
Nonstop2h 16mSpirit Airlines
Deal found 9/10$129

Cheapflights Fare Finder

 
Customize your flight search to find flights from New Orleans to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from New Orleans to Chicago that are best for you.

Fly from

New Orleans

Fly to

Chicago

Route

Depart

Return

Price

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Fri 11/14

6:20 am-8:40 am

Nonstop2h 20m

Chicago Midway

Mon 11/17

8:40 am-11:05 am

Nonstop2h 25m

$156

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Sat 10/11

11:10 am-1:30 pm

Nonstop2h 20m

Chicago Midway

Sun 10/12

10:40 pm-12:55 am

Nonstop2h 15m

$157

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Sat 10/4

6:30 am-8:50 am

Nonstop2h 20m

Chicago Midway

Tue 10/7

8:30 pm-10:45 pm

Nonstop2h 15m

$167

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Fri 10/24

6:05 am-8:25 am

Nonstop2h 20m

Chicago Midway

Sun 10/26

10:40 pm-12:55 am

Nonstop2h 15m

$189

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Sat 10/4

2:20 pm-4:40 pm

Nonstop2h 20m

Chicago Midway

Mon 10/6

5:25 am-9:55 am

1 stop4h 30m

$195

New OrleansChicago

MSY - MDW

MSYMDW

New Orleans Louis Armstrong

Thu 10/23

6:05 am-8:25 am

Nonstop2h 20m

Chicago Midway

Fri 10/24

9:25 pm-11:40 pm

Nonstop2h 15m

$198

New OrleansChicago

MSY - ORD

MSYORD

New Orleans Louis Armstrong

Wed 10/1

10:28 am-1:07 pm

Nonstop2h 39m

Chicago O'Hare Intl

Sun 10/5

7:10 am-9:38 am

Nonstop2h 28m

$206

New OrleansChicago

MSY - ORD

MSYORD

New Orleans Louis Armstrong

Sat 9/27

3:58 pm-6:38 pm

Nonstop2h 40m

Chicago O'Hare Intl

Tue 9/30

5:50 pm-11:15 pm

1 stop5h 25m

$207

New OrleansChicago

MSY - ORD

MSYORD

New Orleans Louis Armstrong

Sat 9/27

7:00 am-9:40 am

Nonstop2h 40m

Chicago O'Hare Intl

Sat 10/4

2:20 pm-7:57 pm

1 stop5h 37m

$207

New OrleansChicago

MSY - ORD

MSYORD

New Orleans Louis Armstrong

Sat 10/11

4:52 pm-11:58 pm

1 stop7h 06m

Chicago O'Hare Intl

Sat 10/18

10:30 am-4:04 pm

1 stop5h 34m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 49 results
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The best insider tips for New Orleans to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your New Orleans to Chicago trip
Airlines
Southwest

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.

Read more about Southwestby Marisa Garcia
Spirit Airlines

Spirit's Big Front Seats offer 11 inches more legroom, ideal for comfort on short flights.


Use Spirit's self-service bag drop for quick check-in; print boarding pass to avoid fees.

Read more about Spirit Airlinesby Daniel Scheffler
United Airlines

United's Economy Plus offers extra legroom, ideal for comfort on domestic routes.


Prepay for checked bags on United to save fees; free for premium cabin or members.

Read more about United Airlinesby Harriet Baskas
Airports
MSY

MSY's TSA security checkpoint averages a 15-minute wait, making it efficient for early morning flights to Chicago.

Read more about MSYby Brandon Schultz
ORD

Use the 'L' train from ORD for a quick, reliable trip to downtown Chicago, avoiding traffic delays.

Read more about ORDby Ramsey Qubein
MDW

The Orange Line train from MDW takes less than 30 minutes to reach downtown Chicago, offering a convenient city connection.

Read more about MDWby Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

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.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Brandon Schultz

Brandon Schultz

Expert on MSY

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

Best time to book a flight from New Orleans to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from New Orleans with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from New Orleans to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from New Orleans to Chicago. Price data was last updated on August 29, 2025.

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 73 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from New Orleans to Chicago?

Currently, August is the cheapest month in which you can book a flight from New Orleans to Chicago (average of $245). Flying from New Orleans to Chicago in March is currently the most expensive (average of $321). 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.

What is the cheapest time of day to fly from MSY to CHI?

Find hourly flight availability from New Orleans to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

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 70% versus a flight at noon.

What is the cheapest day to fly from New Orleans to Chicago?

Use this chart to determine the cheapest time to fly round-trip from New Orleans to Chicago. Price data was last updated on September 7, 2025.

Travelers seeking maximum savings on their New Orleans to Chicago flight should consider departing on Saturday 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.

Weekly flight availability from New Orleans to Chicago

Explore weekly flight availability from New Orleans to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 11, 2025.

The most flights from MSY to CHI are scheduled on a Thursday (30 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (15 on average).

How much does it cost to fly round-trip from New Orleans to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 11, 2025.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from New Orleans to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from New Orleans to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from New Orleans to Chicago?

    New Orleans Louis Armstrong (MSY) is the airport you will fly out of if you book a flight from New Orleans to Chicago. You should not have trouble finding flights to Chicago from Louis Armstrong; the airport handles an average of 24 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 5 airlines have flights from the New Orleans airport to Chicago. It is only a 11.4 mi journey to Louis Armstrong (MSY) from New Orleans’s city center.

  • How long is the flight from New Orleans to Chicago?

    A quick flight from New Orleans to Chicago can take about 2h 20m. Southwest provides one of the quickest options available for as low as $156. Airlines will cover a distance of 827 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from New Orleans to Chicago round-trip?

    Our cheapest airline available from New Orleans to Chicago is Spirit Airlines. Our recent data shows that you can find tickets from as low as $62 on this airline. Additional options worth looking into are United Airlines and American Airlines, starting at $135 and $151 round-trip. Users have found that Spirit Airlines is 74% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from New Orleans to Chicago one-way?

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $67. However, be on the lookout for offers from Southwest and Frontier, as they are both options that can get you from New Orleans to Chicago for a low price.

  • What are the most popular routes from New Orleans to Chicago?

    Most travelers choose New Orleans Louis Armstrong - Chicago O'Hare Intl, New Orleans Louis Armstrong - Chicago Midway or New Orleans Louis Armstrong - Chicago Greater Rockford when deciding on the best route from New Orleans to Chicago.

  • What are the most reliable airlines from New Orleans to Chicago?

    No one likes to see their flight delayed. When booking a flight from New Orleans to Chicago consider choosing Turkish Airlines (92%), Japan Airlines (89%) or Envoy Air (88%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from New Orleans to Chicago?

    Looking for the cheapest flight from New Orleans to Chicago? While on average our users pay $851, our data indicates the cheapest price to be $58. The most popular route (New Orleans Louis Armstrong - Chicago O'Hare Intl), is priced around $86.

  • Can I find deals for flights from New Orleans to Chicago that include hotel bookings?

    Yes. In addition to deals on New Orleans to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from New Orleans to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New Orleans to Chicago.

  • Can I find deals for business class flights from New Orleans to Chicago?

    Yes. Cheapflights offers flight deals from New Orleans to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New Orleans to Chicago?

    Currently, August is the cheapest month in which you can book a flight from New Orleans to Chicago (average of $245). Flying from New Orleans to Chicago in March is currently the most expensive (average of $321). 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for New Orleans to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from New Orleans to Chicago

Discover the top 5 airlines that operate flights from New Orleans to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$62Average$186FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$135Average$334FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$151Average$288FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$189Average$289FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$287FlexibilityNo cancel feeOn-timeN/A

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