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$147+ Cheap flights from Fort Myers (RSW) 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — CHI
Aug 27 — Sep 31
Thu 8/27
Thu 9/3
1 adult, Economy
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Find cheap flights from Fort Myers to Chicago with Cheapflights

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Cheapflights Tip: The best prices from Fort Myers SW Florida Intl to Chicago are usually found in January or February, booked 29 days in advance, depart on a Thursday or Saturday and return on a Wednesday

Cheap flight deals from Fort Myers to Chicago

Cheapest flights from Fort Myers to Chicago
Explore the most affordable flight options available from Fort Myers to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 28, 2026.

This American Airlines deal was found by Cheapflights users on 7/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1311:27 am
RSW
-
ORD
Nonstop3h 23m
American Airlines
Mon 8/176:45 am
ORD
-
RSW
Nonstop2h 52m
American Airlines
Deal found 7/23$275
This Southwest deal was found by Cheapflights users on 7/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:10 am
RSW
-
MDW
Nonstop2h 45m
Southwest
Mon 8/241:00 pm
MDW
-
RSW
Nonstop2h 45m
Southwest
Deal found 7/23$275
This American Airlines deal was found by Cheapflights users on 7/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:07 am
RSW
-
ORD
Nonstop3h 23m
American Airlines
Wed 8/267:04 pm
ORD
-
RSW
Nonstop2h 55m
American Airlines
Deal found 7/23$281
This United Airlines deal was found by Cheapflights users on 7/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:15 am
RSW
-
ORD
Nonstop3h 14m
United Airlines
Mon 9/77:15 am
ORD
-
RSW
Nonstop3h 06m
United Airlines
Deal found 7/24$283
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:55 am
RSW
-
MDW
Nonstop2h 50m
Southwest
Sat 8/2211:00 am
MDW
-
RSW
Nonstop2h 40m
Southwest
Deal found 7/27$283
This United Airlines deal was found by Cheapflights users on 7/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:15 am
RSW
-
ORD
Nonstop3h 14m
United Airlines
Sat 9/197:15 am
ORD
-
RSW
Nonstop3h 06m
United Airlines
Deal found 7/25$284
This Southwest deal was found by Cheapflights users on 7/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:15 am
RSW
-
MDW
Nonstop2h 45m
Southwest
Wed 9/96:00 pm
MDW
-
RSW
Nonstop2h 50m
Southwest
Deal found 7/24$284
This United Airlines deal was found by Cheapflights users on 7/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:14 pm
RSW
-
ORD
1 stop7h 12m
United Airlines
Mon 8/175:51 pm
ORD
-
RSW
Nonstop3h 06m
United Airlines
Deal found 7/23$285
This Southwest deal was found by Cheapflights users on 7/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:20 am
RSW
-
MDW
1 stop5h 45m
Southwest
Sat 8/2211:00 am
MDW
-
RSW
Nonstop2h 40m
Southwest
Deal found 7/23$285
This Frontier deal was found by Cheapflights users on 7/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/103:53 pm
RSW
-
ORD
Nonstop3h 21m
Frontier
Sun 12/1310:52 am
ORD
-
RSW
Nonstop3h 06m
Frontier
Deal found 7/25$286
This JetBlue deal was found by Cheapflights users on 7/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/316:00 am
RSW
-
ORD
1 stop8h 20m
JetBlue
Mon 11/22:15 pm
ORD
-
RSW
1 stop8h 22m
JetBlue
Deal found 7/27$289
This American Airlines deal was found by Cheapflights users on 7/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:00 am
RSW
-
ORD
1 stop5h 15m
American Airlines
Thu 9/106:50 am
ORD
-
RSW
Nonstop3h 01m
American Airlines
Deal found 7/23$290

Find flight deals from Fort Myers to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Fort Myers (RSW) 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 July 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$275
(American Airlines)

One-way from

$147
(United Airlines)

Popular in

June

Cheapest in

January

Average price

$335
Provider with most accurate pricing for Fort Myers SW Florida Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Fort Myers SW Florida Intl-Chicago (CHI) flights.
Search Deals
From Fort Myers SW Florida Intl to Chicago (CHI)
Search Deals
One-way flight from Fort Myers SW Florida Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Fort Myers 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 July 28, 2026.
Use the filters below to find and compare flights from Fort Myers to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Mon 8/24

6:50 am-8:40 am

Nonstop2h 50m

Chicago Midway

Tue 9/1

6:00 pm-9:45 pm

Nonstop2h 45m

$283

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 8/13

7:20 am-12:25 pm

2 stops6h 05m

Chicago Midway

Mon 8/17

1:00 pm-4:45 pm

Nonstop2h 45m

$290

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Mon 8/17

4:40 pm-6:59 pm

Nonstop3h 19m

Chicago O'Hare Intl

Wed 8/19

6:30 am-3:55 pm

1 stop8h 25m

$293

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Mon 9/14

1:25 pm-7:45 pm

1 stop7h 20m

Chicago Midway

Wed 9/16

6:00 pm-9:50 pm

Nonstop2h 50m

$293

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 8/22

1:19 pm-6:59 pm

1 stop6h 40m

Chicago O'Hare Intl

Sat 8/29

6:40 am-12:13 pm

1 stop4h 33m

$295

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Wed 8/19

7:30 am-1:05 pm

2 stops6h 35m

Chicago Midway

Thu 8/20

1:00 pm-4:45 pm

Nonstop2h 45m

$298

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 8/15

6:25 am-1:05 pm

2 stops7h 40m

Chicago Midway

Mon 8/17

1:00 pm-4:45 pm

Nonstop2h 45m

$298

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Mon 8/24

3:30 pm-8:55 pm

1 stop6h 25m

Chicago O'Hare Intl

Tue 9/1

8:05 am-2:24 pm

1 stop5h 19m

$303

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Mon 8/24

6:25 pm-9:55 pm

1 stop4h 30m

Chicago Midway

Mon 8/31

1:20 pm-10:00 pm

2 stops7h 40m

$308

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 9/5

12:22 pm-4:59 pm

1 stop5h 37m

Chicago Midway

Thu 9/10

4:30 pm-12:35 am

1 stop7h 05m

$310

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 45 resultsSorted by cheapest first
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Compare providers for flights from Fort Myers to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Fort Myers to Chicago in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
JustAirTicketPrice Accuracy-Trust Score*1 star
Super.comPrice Accuracy-Trust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
MytripPrice Accuracy2 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Fort Myers-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Fort Myers-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Fort Myers-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Fort Myers-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Fort Myers-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Fort Myers to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Fort Myers 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 Fort Myers to Chicago

What is the cheapest month to book a flight from Fort Myers to Chicago?

Currently, February is the cheapest month in which you can book a flight from Fort Myers to Chicago (average of $194). Flying from Fort Myers to Chicago in June is currently the most expensive (average of $356). 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 RSW to CHI?

Find hourly flight availability from Fort Myers 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 July 28, 2026.

It’s typically best to fly out from Fort Myers to Chicago in the evening. Doing so could potentially save you 24% on the flight price compared to flying at noon, which is usually more expensive.

Weekly flight availability from Fort Myers to Chicago

Explore weekly flight availability from Fort Myers 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 July 28, 2026.

The most flights from RSW to CHI are scheduled on a Monday (20 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (13 on average).

How much does it cost to fly round-trip from Fort Myers to Chicago?

Airfare is typical for this route at the moment.
Fort Myers to Chicago flights typically cost between $182 and $298 in August.
The cheapest round-trip price found within the last 5 days was $275 on American Airlines (Aug 13-Aug 17).

How far ahead should I book a flight from Fort Myers to Chicago?

The price you pay for your flight from Fort Myers to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 72 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest day to fly from Fort Myers to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Fort Myers to Chicago. Price data was last updated on July 25, 2026.

Travelers seeking maximum savings on their Fort Myers to Chicago flight should consider departing on Sunday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Fort Myers to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Fort Myers to Chicago trip
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

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
Marisa Garcia

Marisa Garcia

Expert on Southwest

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
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

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
Matt Meltzer

Matt Meltzer

Expert on RSW

Matt Meltzer has been a travel writer for over a decade, covering U.S. domestic locations and hotels for Thrillist, Fifty Grande, Matador Network, Conde Nast Traveler, and other top publications. He's won multiple travel journalism awards from the Society of American Travel Writers and North American Travel Journalists Association, and currently resides in South Florida.

Read more

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 July 28, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Fort Myers to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,229 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,229 reviews
Southwest
8.0
Very good
4,229 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
10,046 reviews
Southwest
8.0
Very good
4,229 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,841 reviews
Southwest
8.0
Very good
4,229 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
JetBlue
7.1
Good
3,027 reviews
Southwest
8.0
Very good
4,229 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,753 reviews
Southwest
8.0
Very good
4,229 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

Find useful and relevant information for your journey from Fort Myers 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 Fort Myers to Chicago?

    For a flight from Fort Myers to Chicago, you will be flying from SW Florida Intl. Fort Myers SW Florida Intl (RSW) is just 10.0 mi from the center of the city. SW Florida Intl is the only Fort Myers airport and it handles 17 outbound flights to Chicago per day. 5 airlines have flights to Chicago from Fort Myers SW Florida Intl on a regular basis.

  • How long is the flight from Fort Myers to Chicago?

    Airlines like Southwest, United Airlines, and Delta fly from Fort Myers to Chicago in about 2h 50m. The time it takes to get you to your destination can typically vary by up to 3h 50m. Airlines will cover a distance of 1106 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Fort Myers to Chicago round-trip?

    Our cheapest airline available from Fort Myers to Chicago is Frontier. Our recent data shows that you can find tickets from as low as $43 on this airline. Additional options worth looking into are JetBlue and United Airlines, starting at $105 and $159 round-trip. You may be able to fly from Fort Myers to Chicago for 84% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Fort Myers to Chicago one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $42. Southwest flights start at $78 while deals on American Airlines start at $79 one-way.

  • What are the most popular routes from Fort Myers to Chicago?

    While some choose either Fort Myers SW Florida Intl - Chicago Midway or Fort Myers SW Florida Intl - Chicago Greater Rockford, Fort Myers SW Florida Intl - Chicago O'Hare Intl is the most popular route from Fort Myers to Chicago.

  • What are the most reliable airlines from Fort Myers to Chicago?

    The top 3 most reliable airlines when flying from Fort Myers to Chicago are Frontier (100%), Volaris (100%) and SWISS (90%).

  • What are the cheapest flights from Fort Myers to Chicago?

    On average you can expect to pay $2,090 for a flight from Fort Myers to Chicago. The cheapest flight overall is $139 while the most popular route, (Fort Myers SW Florida Intl - Chicago O'Hare Intl) is currently priced at $280.

  • Can I find deals for flights from Fort Myers to Chicago that include hotel bookings?

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

  • How can I find direct flights from Fort Myers to Chicago?

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

  • Can I find deals for business class flights from Fort Myers to Chicago?

    Yes. Cheapflights offers flight deals from Fort Myers 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 Fort Myers to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Fort Myers to Chicago (average of $194). Flying from Fort Myers to Chicago in June is currently the most expensive (average of $356). 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Top 5 airlines flying from Fort Myers to Chicago

Discover the top 5 airlines that operate flights from Fort Myers 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 July 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$43Average$98FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$105Average$284FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$159Average$315FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$161Average$304FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$183Average$349FlexibilityNo cancel feeOn-time63%

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