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$72+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Fort Myers SW Florida Intl to Chicago are usually found in January or August, booked 86 days in advance, depart on a Thursday or Friday and return on a Wednesday

Cheap 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 September 17, 2025.

Round-trip from

$119
(Cheapflightsfares)

One-way from

$72
(Cheapflightsfares)

Popular in

October

Cheapest in

January

Average price

$191
From Fort Myers SW Florida Intl to Chicago (CHI)
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One-way flight from Fort Myers SW Florida Intl to Chicago (CHI)
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Highest demand for flights based on searches. 6% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/166:40 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Sun 10/194:51 pmORD - RSW
Nonstop2h 50mSpirit Airlines
Deal found 9/15$119
This Priceline deal was found by Cheapflights users on 9/15. 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 10/246:40 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Sun 10/265:28 pmORD - RSW
Nonstop2h 49mSpirit Airlines
Deal found 9/15$120
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/27:00 amRSW - ORD
Nonstop3h 13mSpirit Airlines
Mon 10/66:16 pmORD - RSW
Nonstop2h 53mSpirit Airlines
Deal found 9/15$123
This Priceline deal was found by Cheapflights users on 9/15. 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 10/2412:27 pmRSW - ORD
1 stop6h 13mMultiple Airlines
Sun 10/265:28 pmORD - RSW
Nonstop2h 49mMultiple Airlines
Deal found 9/15$132
This Priceline deal was found by Cheapflights users on 9/15. 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.
Thu 9/257:24 pmRSW - ORD
1 stop5h 46mMultiple Airlines
Mon 9/295:23 pmORD - RSW
Nonstop2h 53mMultiple Airlines
Deal found 9/15$136
This Priceline deal was found by Cheapflights users on 9/15. 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 10/316:22 amRSW - ORD
Nonstop2h 54mMultiple Airlines
Mon 11/38:26 amORD - RSW
1 stop11h 07mMultiple Airlines
Deal found 9/15$138
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Fri 10/106:40 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Sun 10/124:51 pmORD - RSW
Nonstop2h 50mSpirit Airlines
Deal found 9/15$139
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/27:00 amRSW - ORD
Nonstop3h 13mSpirit Airlines
Sun 10/54:51 pmORD - RSW
Nonstop2h 50mSpirit Airlines
Deal found 9/15$143
This Priceline deal was found by Cheapflights users on 9/16. 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.
Thu 10/231:01 pmRSW - MDW
1 stop8h 20mFrontier
Sun 10/266:20 amMDW - RSW
1 stop4h 56mFrontier
Deal found 9/16$143
This Frontier deal was found by Cheapflights users on 9/15. 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 11/61:13 pmRSW - ORD
1 stop11h 58mFrontier
Mon 11/108:26 amORD - RSW
1 stop11h 07mFrontier
Deal found 9/15$144
This Frontier deal was found by Cheapflights users on 9/15. 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 10/161:01 pmRSW - MDW
1 stop8h 20mFrontier
Sun 10/196:20 amMDW - RSW
1 stop4h 56mFrontier
Deal found 9/15$144
This Trip.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/306:22 amRSW - ORD
Nonstop2h 54mSpirit Airlines
Sun 11/25:28 pmORD - RSW
Nonstop2h 49mSpirit Airlines
Deal found 9/15$147

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 September 17, 2025.
Use the filters below to find and compare flights from Fort Myers to Chicago that are best for you.

Fly from

Fort Myers

Fly to

Chicago

Route

Depart

Return

Price

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 10/16

6:40 am-8:34 am

Nonstop2h 54m

Chicago O'Hare Intl

Mon 10/20

6:16 pm-10:09 pm

Nonstop2h 53m

$119

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 10/10

6:40 am-8:34 am

Nonstop2h 54m

Chicago O'Hare Intl

Mon 10/13

6:16 pm-10:09 pm

Nonstop2h 53m

$119

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 10/31

6:22 am-8:16 am

Nonstop2h 54m

Chicago O'Hare Intl

Mon 11/3

5:28 pm-9:17 pm

Nonstop2h 49m

$119

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 2/28

8:35 pm-10:45 pm

Nonstop3h 10m

Chicago O'Hare Intl

Tue 3/3

7:00 am-10:51 am

Nonstop2h 51m

$130

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 10/3

7:00 am-9:13 am

Nonstop3h 13m

Chicago O'Hare Intl

Sun 10/5

4:51 pm-8:41 pm

Nonstop2h 50m

$143

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 11/14

6:50 am-8:45 am

Nonstop2h 55m

Chicago Midway

Sun 11/16

5:35 am-9:20 am

Nonstop2h 45m

$159

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 10/24

6:40 am-8:30 am

Nonstop2h 50m

Chicago Midway

Sun 10/26

8:30 pm-12:10 am

Nonstop2h 40m

$159

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 10/30

6:40 am-8:30 am

Nonstop2h 50m

Chicago Midway

Mon 11/3

5:35 am-10:55 am

1 stop4h 20m

$191

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 12/12

12:43 pm-2:55 pm

Nonstop3h 12m

Chicago O'Hare Intl

Mon 12/15

7:35 am-3:44 pm

1 stop7h 09m

$198

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 10/11

4:05 pm-5:55 pm

Nonstop2h 50m

Chicago Midway

Sun 10/12

7:20 am-1:25 pm

1 stop5h 05m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 49 results
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The best insider tips for Fort Myers 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 Fort Myers to Chicago trip
Airlines
Spirit Airlines

Spirit's Big Front Seats offer 11 inches more legroom, ideal for a comfortable short flight.


Spirit's self-service bag drop saves time; print your boarding pass to avoid extra fees.

Read more about Spirit Airlinesby Daniel Scheffler
United Airlines

United's Economy Plus offers extra legroom and priority boarding for a more comfortable flight experience.


United's Basic Economy restricts carry-ons; consider upgrading for more baggage flexibility.

Read more about United Airlinesby Harriet Baskas
Southwest

Southwest offers free messaging and in-flight entertainment streamed to your device.


Southwest's open seating policy allows you to choose any available seat upon boarding.

Read more about Southwestby Marisa Garcia
Airports
RSW

During peak tourist seasons, plan an extra 20 minutes at RSW for check-in due to smaller airline ticket counters.

Read more about RSWby Matt Meltzer
ORD

Consider taking the “L” train from ORD to the city center to avoid Chicago traffic delays.

Read more about ORDby Ramsey Qubein
MDW

Use the Orange Line train for a quick, 30-minute ride from MDW to Chicago's city center.

Read more about MDWby Ramsey Qubein
Our travel experts
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
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
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
Matt Meltzer

Matt Meltzer

Expert on RSW

Matt Meltzer

Matt Meltzer

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

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

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

Use this chart to determine the optimal time to book a round-trip flight from Fort Myers to Chicago. Price data was last updated on September 12, 2025.

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 86 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 Fort Myers to Chicago?

Currently, August is the cheapest month in which you can book a flight from Fort Myers to Chicago (average of $245). Flying from Fort Myers 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 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 September 17, 2025.

It’s typically best to fly out from Fort Myers to Chicago in the evening. Doing so could potentially save you 46% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 September 14, 2025.

Travelers seeking maximum savings on their Fort Myers to Chicago flight should consider departing on Wednesday 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.

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 September 17, 2025.

The most flights from RSW to CHI are scheduled on a Monday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).

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 17, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American 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
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
United Airlines
7.4
Good
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.8
Fair
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 15 outbound flights to Chicago per day. 6 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 Spirit Airlines and Southwest fly from Fort Myers to Chicago in about 2h 54m. The time it takes to get you to your destination is usually consistent. Airlines will cover a distance of 1122 mi. Generally, flights for this route are nonstop.

  • 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 $46 on this airline. Additional options worth looking into are Spirit Airlines and American Airlines, starting at $67 and $158 round-trip. You may be able to fly from Fort Myers to Chicago for 80% less than the average price by searching for these airlines.

  • 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 Spirit Airlines (91%), SWISS (87%) and United Airlines (87%).

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

    On average you can expect to pay $999 for a flight from Fort Myers to Chicago. The cheapest flight overall is $79 while the most popular route, (Fort Myers SW Florida Intl - Chicago O'Hare Intl) is currently priced at $119.

  • 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, August is the cheapest month in which you can book a flight from Fort Myers to Chicago (average of $245). Flying from Fort Myers 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 Fort Myers to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Fort Myers to Chicago

Discover the top 6 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$132FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$156FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$158Average$263FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$166Average$340FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$183Average$385FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$386FlexibilityNo cancel feeOn-timeN/A

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