O'Hare Intl

$56+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — ORD
Feb 27 — Mar 61
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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

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3. Compare prices and book

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Cheapflights Tip: The best prices from Fort Myers SW Florida Intl to Chicago O'Hare Intl are usually found in January or October, booked 87 days in advance, depart on a Friday or Thursday and return on a Tuesday

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 January 28, 2026.

This Trip.com deal was found by Cheapflights users on 1/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:00 am
RSW
-
ORD
Nonstop3h 13m
Spirit Airlines
Tue 3/35:22 pm
ORD
-
RSW
Nonstop2h 58m
Spirit Airlines
Deal found 1/26$72
This Frontier deal was found by Cheapflights users on 1/25. 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.
Sat 2/146:49 pm
RSW
-
ORD
Nonstop3h 32m
Frontier
Sun 2/226:30 am
ORD
-
RSW
Nonstop3h 09m
Frontier
Deal found 1/25$73
This Priceline deal was found by Cheapflights users on 1/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:51 pm
RSW
-
ORD
Nonstop3h 10m
Spirit Airlines
Sat 3/75:22 pm
ORD
-
RSW
Nonstop2h 58m
Spirit Airlines
Deal found 1/26$74
This Super.com deal was found by Cheapflights users on 1/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:00 am
RSW
-
ORD
Nonstop3h 13m
Spirit Airlines
Mon 2/237:20 am
ORD
-
RSW
Nonstop2h 56m
Spirit Airlines
Deal found 1/27$76
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:00 am
RSW
-
ORD
Nonstop3h 13m
Spirit Airlines
Sun 2/225:22 pm
ORD
-
RSW
Nonstop2h 58m
Spirit Airlines
Deal found 1/27$77
This Priceline deal was found by Cheapflights users on 1/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
RSW
-
ORD
Nonstop3h 13m
Spirit Airlines
Tue 3/37:20 am
ORD
-
RSW
Nonstop2h 56m
Spirit Airlines
Deal found 1/27$78
This Super.com deal was found by Cheapflights users on 1/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/127:51 pm
RSW
-
ORD
Nonstop3h 10m
Spirit Airlines
Mon 2/165:22 pm
ORD
-
RSW
Nonstop2h 58m
Spirit Airlines
Deal found 1/26$82
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
RSW
-
ORD
Nonstop3h 13m
Spirit Airlines
Tue 2/245:22 pm
ORD
-
RSW
Nonstop2h 58m
Spirit Airlines
Deal found 1/27$84
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/147:51 pm
RSW
-
ORD
Nonstop3h 10m
Spirit Airlines
Sun 2/157:20 am
ORD
-
RSW
Nonstop2h 56m
Spirit Airlines
Deal found 1/27$87
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/107:49 pm
RSW
-
ORD
Nonstop3h 19m
Spirit Airlines
Tue 2/247:20 am
ORD
-
RSW
Nonstop2h 56m
Spirit Airlines
Deal found 1/27$88

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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$72
(Trip.com)

One-way from

$56
(Cheapflightsfares)

Popular in

December

Cheapest in

January

Average price

$191
Provider with most accurate pricing for Fort Myers SW Florida Intl-Chicago O'Hare Intl flight deals.
Provider most trusted by Cheapflights users for Fort Myers SW Florida Intl-Chicago O'Hare Intl flights.
From Fort Myers SW Florida Intl to Chicago O'Hare Intl
One-way flight from Fort Myers SW Florida Intl to Chicago O'Hare Intl
Highest demand for flights based on searches. 4% potential increase in price ($10 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Average for round-trip flights in January 2026

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 January 28, 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

Fort Myers

Fly to

O'Hare Intl

Route

Depart

Return

Price

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 2/14

6:49 pm-9:21 pm

Nonstop3h 32m

Chicago O'Hare Intl

Sun 2/22

6:30 am-10:39 am

Nonstop3h 09m

$73

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Wed 3/4

6:00 am-12:04 pm

1 stop7h 04m

Chicago O'Hare Intl

Tue 3/10

12:39 pm-11:52 pm

1 stop10h 13m

$181

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 3/7

7:50 pm-11:56 pm

1 stop5h 06m

Chicago O'Hare Intl

Wed 3/11

5:59 pm-12:36 am

1 stop5h 37m

$217

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sun 3/22

9:54 pm-11:59 pm

Nonstop3h 05m

Chicago O'Hare Intl

Wed 3/25

7:40 pm-11:36 pm

Nonstop2h 56m

$230

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Wed 3/4

9:15 am-11:40 am

Nonstop3h 25m

Chicago O'Hare Intl

Sat 3/7

6:32 pm-10:37 pm

Nonstop3h 05m

$237

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Wed 3/4

6:00 am-1:20 pm

1 stop8h 20m

Chicago O'Hare Intl

Mon 3/9

11:10 am-6:52 pm

1 stop6h 42m

$237

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 3/5

5:35 am-10:14 am

1 stop5h 39m

Chicago O'Hare Intl

Mon 3/9

5:40 pm-12:01 am

1 stop5h 21m

$237

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Wed 3/4

6:00 am-12:04 pm

1 stop7h 04m

Chicago O'Hare Intl

Wed 3/11

12:44 pm-11:52 pm

1 stop10h 08m

$242

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 3/5

10:10 am-12:35 pm

Nonstop3h 25m

Chicago O'Hare Intl

Tue 3/10

12:50 pm-4:52 pm

Nonstop3h 02m

$257

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 3/6

2:25 pm-4:51 pm

Nonstop3h 26m

Chicago O'Hare Intl

Wed 3/11

4:10 pm-8:12 pm

Nonstop3h 02m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 24 results
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2
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*2 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
eDreamsPrice 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?

Use this chart to determine the optimal time to book a round-trip flight from Fort Myers to O'Hare Intl. Price data was last updated on January 23, 2026.

The best time to book flights from Fort Myers to Chicago O'Hare Intl Airport is 87 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, March is the cheapest month in which you can book a flight from Fort Myers to Chicago O'Hare Intl Airport (average of $51). Flying from Fort Myers to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $116). 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 January 28, 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 evening, which can drop the price by up to 53% versus a flight in the afternoon.

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 January 24, 2026.

Travelers seeking maximum savings on their Fort Myers to Chicago O'Hare Intl Airport flight should consider departing on Thursday 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 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
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

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.

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.

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.

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.

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 January 28, 2026.
Read through reviews of airlines operating flights from Fort Myers to Chicago O'Hare Intl Airport, such as United Airlines, American Airlines, and Spirit Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 14 outbound flights to Chicago O'Hare Intl per day from 4 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 32m. 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 $37 on this airline. Additional options worth looking into are Spirit Airlines and United Airlines, starting at $58 and $153 round-trip. These flights start at 83% 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 $31 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $40 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 United Airlines (82%), Qatar Airways (79%) and Emirates (75%).

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

    On average you can expect to pay $985 for a flight from Fort Myers to Chicago O'Hare Intl Airport. The cheapest flight overall is $44 while the most popular route, (Fort Myers SW Florida Intl - Chicago O'Hare Intl) is currently priced at $62.

  • 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, March is the cheapest month in which you can book a flight from Fort Myers to Chicago O'Hare Intl Airport (average of $51). Flying from Fort Myers to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $116). 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
Schaumburg
Rosemont
Naperville
Gurnee
Elgin
Hoffman Estates
Beloit
Delavan
Oak Brook
Des Plaines
Downers Grove
Elk Grove Village
Skokie
Libertyville
Lake Geneva
Waukegan
Bridgeview
Kenosha
Warrenville
Aurora

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Top 4 airlines flying from Fort Myers to O'Hare Intl

Discover the top 4 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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$101FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$58Average$152FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$153Average$285FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$252FlexibilityNo cancel feeOn-time71%

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