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O'Hare Intl

$125+ Cheap flights from Fort Myers (RSW) to O'Hare Intl (ORD)

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 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — ORD
Jul 3 — Jul 101
Fri 7/3
Fri 7/10
1 adult, Economy
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Find cheap flights from Fort Myers to O'Hare Intl with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Fort Myers SW Florida Intl to Chicago O'Hare Intl are usually found in February or January, booked 73 days in advance, depart on a Thursday or Friday and return on a Wednesday

Cheap flight deals from Fort Myers to O'Hare Intl

Cheapest flights from Fort Myers to O'Hare Intl
Explore the most affordable flight options available from Fort Myers to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 3, 2026.

This United Airlines deal was found by Cheapflights users on 6/2. 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 7/2212:28 pm
RSW
-
ORD
Nonstop3h 25m
United Airlines
Mon 7/2710:35 am
ORD
-
RSW
Nonstop3h 09m
United Airlines
Deal found 6/2$295
This American Airlines deal was found by Cheapflights users on 5/30. 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.
Tue 7/146:15 am
RSW
-
ORD
Nonstop3h 18m
American Airlines
Tue 7/2112:41 pm
ORD
-
RSW
Nonstop2h 53m
American Airlines
Deal found 5/30$297
This American Airlines deal was found by Cheapflights users on 6/1. 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 6/2412:47 pm
RSW
-
ORD
Nonstop3h 22m
American Airlines
Wed 7/16:48 am
ORD
-
RSW
Nonstop2h 53m
American Airlines
Deal found 6/1$313
This Delta deal was found by Cheapflights users on 5/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:34 pm
RSW
-
ORD
1 stop6h 25m
Delta
Tue 7/73:22 pm
ORD
-
RSW
1 stop4h 51m
Delta
Deal found 5/31$315
This American Airlines deal was found by Cheapflights users on 5/31. 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.
Tue 10/136:15 am
RSW
-
ORD
Nonstop3h 24m
American Airlines
Fri 10/166:45 am
ORD
-
RSW
Nonstop2h 53m
American Airlines
Deal found 5/31$322
This American Airlines deal was found by Cheapflights users on 6/3. 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.
Fri 7/1710:00 am
RSW
-
ORD
1 stop7h 46m
American Airlines
Thu 7/237:29 pm
ORD
-
RSW
Nonstop3h 00m
American Airlines
Deal found 6/3$325
This United Airlines deal was found by Cheapflights users on 5/31. 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.
Tue 7/144:39 pm
RSW
-
ORD
Nonstop3h 21m
United Airlines
Sun 7/197:05 am
ORD
-
RSW
Nonstop3h 09m
United Airlines
Deal found 5/31$326
This United Airlines deal was found by Cheapflights users on 5/29. 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.
Tue 6/234:39 pm
RSW
-
ORD
Nonstop3h 21m
United Airlines
Wed 6/247:05 am
ORD
-
RSW
Nonstop3h 09m
United Airlines
Deal found 5/29$331

Find flight deals from Fort Myers to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Fort Myers (RSW) to O'Hare Intl (ORD). 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 June 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$291
(American Airlines)

One-way from

$125
(Delta)

Popular in

May

Cheapest in

February

Average price

$291
Provider with most accurate pricing for Fort Myers SW Florida Intl-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Fort Myers SW Florida Intl-Chicago O'Hare Intl flights.
Search Deals
From Fort Myers SW Florida Intl to Chicago O'Hare Intl
Search Deals
One-way flight from Fort Myers SW Florida Intl to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($61 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in June 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Fort Myers to O'Hare Intl 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 June 3, 2026.
Use the filters below to find and compare flights from Fort Myers to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Tue 8/25

4:41 pm-7:00 pm

Nonstop3h 19m

Chicago O'Hare Intl

Sat 9/5

7:15 am-11:21 am

Nonstop3h 06m

$295

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 8/15

5:35 am-9:40 am

1 stop5h 05m

Chicago O'Hare Intl

Sat 8/22

3:25 pm-9:18 pm

1 stop4h 53m

$315

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Wed 8/19

6:40 am-12:16 pm

1 stop6h 36m

Chicago O'Hare Intl

Tue 8/25

3:31 pm-9:18 pm

1 stop4h 47m

$315

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 7/3

6:34 pm-11:59 pm

1 stop6h 25m

Chicago O'Hare Intl

Thu 7/9

8:03 am-4:44 pm

1 stop7h 41m

$335

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Tue 8/25

8:04 am-2:09 pm

1 stop7h 05m

Chicago O'Hare Intl

Sun 8/30

6:40 am-12:13 pm

1 stop4h 33m

$346

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 8/29

1:19 pm-6:59 pm

1 stop6h 40m

Chicago O'Hare Intl

Sun 9/6

5:28 am-12:13 pm

1 stop5h 45m

$346

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 9/26

5:30 am-9:34 am

1 stop5h 04m

Chicago O'Hare Intl

Sun 9/27

5:30 am-12:07 pm

1 stop5h 37m

$346

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Wed 11/25

2:30 pm-8:20 am

1 stop18h 50m

Chicago O'Hare Intl

Sun 11/29

7:35 pm-10:31 am

1 stop13h 56m

$355

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 7/23

11:25 am-5:39 pm

1 stop7h 14m

Chicago O'Hare Intl

Sun 7/26

7:30 am-10:15 am

1 stop25h 45m

$365

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 10/9

8:00 am-12:37 pm

1 stop5h 37m

Chicago O'Hare Intl

Sun 10/11

5:30 am-1:53 pm

1 stop7h 23m

$366

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/2

Showing 1-10 of 24 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Fort Myers to O'Hare Intl

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 O'Hare Intl in June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
Super.comPrice Accuracy-Trust Score*3 stars
CheapTicketsDealPrice Accuracy1 starTrust Score*3 stars
CheapOairPrice Accuracy3 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 O'Hare Intl Airport 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 O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Fort Myers-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Fort Myers-Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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 O'Hare Intl Airport

How far ahead should I book a flight from Fort Myers to Chicago O'Hare Intl Airport?

The best time to book flights from Fort Myers to Chicago O'Hare Intl Airport is 72 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Fort Myers to Chicago O'Hare Intl Airport?

Currently, February is the cheapest month in which you can book a flight from Fort Myers to Chicago O'Hare Intl Airport (average of $179). Flying from Fort Myers to Chicago O'Hare Intl Airport in May is currently the most expensive (average of $326). 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 ORD?

Find hourly flight availability from Fort Myers to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 3, 2026.

When flying from Fort Myers to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 12% versus a flight in the evening.

What is the cheapest day to fly from Fort Myers to Chicago O'Hare Intl Airport?

Use this chart to determine the cheapest time to fly round-trip from Fort Myers to O'Hare Intl. Price data was last updated on May 30, 2026.

Travelers seeking maximum savings on their Fort Myers to Chicago O'Hare Intl Airport 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.

How much does it cost to fly round-trip from Fort Myers to Chicago O'Hare Intl Airport?

The best insider tips for Fort Myers to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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 O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated June 3, 2026.
Read through reviews of airlines operating flights from Fort Myers to Chicago O'Hare Intl Airport, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,255 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,255 reviews
Southwest
8.0
Very good
4,255 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,773 reviews
Southwest
8.0
Very good
4,255 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,645 reviews
Southwest
8.0
Very good
4,255 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.1
Good
2,980 reviews
Southwest
8.0
Very good
4,255 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.6
Fair
2,921 reviews
Southwest
8.0
Very good
4,255 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Fort Myers to O'Hare Intl. 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 O'Hare Intl?

    Most people fly from Fort Myers SW Florida Intl (RSW) if they book a flight from Fort Myers to Chicago O'Hare Intl. On average, SW Florida Intl has 12 outbound flights to Chicago O'Hare Intl per day from 5 airlines. Fort Myers SW Florida Intl is conveniently located just 10.0 mi from Fort Myers’s city center.

  • How long is the flight from Fort Myers to Chicago O'Hare Intl Airport?

    Departing from Fort Myers to Chicago O'Hare Intl Airport will take you 3h 19m. The distance between Fort Myers and Chicago O'Hare Intl Airport is about 1122 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 O'Hare Intl Airport round-trip?

    Our cheapest airline available from Fort Myers to Chicago O'Hare Intl Airport 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 American Airlines, starting at $105 and $157 round-trip. These flights start at 82% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Fort Myers to Chicago O'Hare Intl Airport one-way?

    One-way options have recently been found by users for as low as $42 on Frontier. Other airlines that offer cheap prices include Southwest from $78 and American Airlines from $79 one-way.

  • What are the most reliable airlines from Fort Myers to Chicago O'Hare Intl Airport?

    The top 3 most reliable airlines when flying from Fort Myers to Chicago O'Hare Intl Airport are Qatar Airways (91%), Air Canada (87%) and United Airlines (84%).

  • What are the cheapest flights from Fort Myers to Chicago O'Hare Intl Airport?

    On average you can expect to pay $696 for a flight from Fort Myers to Chicago O'Hare Intl Airport. The cheapest flight overall is $128 while the most popular route, (Fort Myers SW Florida Intl - Chicago O'Hare Intl) is currently priced at $295.

  • Can I find deals for flights from Fort Myers to O'Hare Intl that include hotel bookings?

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

  • How can I find direct flights from Fort Myers to O'Hare Intl?

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

  • Can I find deals for business class flights from Fort Myers to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Fort Myers to O'Hare Intl 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 O'Hare Intl Airport?

    Currently, February is the cheapest month in which you can book a flight from Fort Myers to Chicago O'Hare Intl Airport (average of $179). Flying from Fort Myers to Chicago O'Hare Intl Airport in May is currently the most expensive (average of $326). 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 O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Rosemont
Schaumburg
Benton Harbor
Naperville
Lake Geneva
Delavan
Oakbrook Terrace
Gurnee
Downers Grove
Des Plaines
Hoffman Estates
Oak Brook
South Holland
Libertyville
Warrenville
Rockford
Great Lakes
Northbrook
Waukegan
Willowbrook

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Top 5 airlines flying from Fort Myers to O'Hare Intl

Discover the top 5 airlines that operate flights from Fort Myers to O'Hare Intl. 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 June 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$43Average$98FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$105Average$277FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$157Average$292FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$158Average$300FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$199Average$347FlexibilityNo cancel feeOn-time63%

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