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$89+ 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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 Tuesday

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 June 12, 2025.

Round-trip from

$148
(Cheapflightsfares)

One-way from

$89
(Southwest)

Popular in

October

Cheapest in

January

Average price

$274
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. 11% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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 7/109:34 pmRSW - ORD
Nonstop3h 10mSpirit Airlines
Thu 7/178:55 amORD - RSW
Nonstop2h 53mSpirit Airlines
Deal found 6/12$148
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2712:28 pmRSW - ORD
Nonstop3h 15mUnited Airlines
Wed 8/274:20 pmORD - RSW
Nonstop2h 58mUnited Airlines
Deal found 6/10$152
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/234:25 pmRSW - MDW
Nonstop2h 50mSouthwest
Tue 8/269:05 amMDW - RSW
Nonstop2h 45mSouthwest
Deal found 6/11$157
This American Airlines deal was found by Cheapflights users on 6/12. 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 8/143:38 pmRSW - ORD
Nonstop3h 17mAmerican Airlines
Sun 8/1710:49 amORD - RSW
Nonstop2h 56mAmerican Airlines
Deal found 6/12$159
This FlightHub deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/107:15 pmRSW - ORD
1 stop6h 07mMultiple Airlines
Tue 7/154:34 pmORD - RSW
Nonstop2h 55mMultiple Airlines
Deal found 6/10$195
This JetBlue deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/510:35 amRSW - ORD
1 stop7h 52mJetBlue
Wed 12/108:40 amORD - RSW
1 stop10h 01mJetBlue
Deal found 6/11$211
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/216:15 pmRSW - ORD
1 stop6h 41mDelta
Sat 8/237:10 amORD - RSW
1 stop7h 06mDelta
Deal found 6/11$217
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/105:45 pmRSW - MDW
1 stop4h 57mDelta
Tue 7/1510:30 amMDW - RSW
1 stop7h 11mDelta
Deal found 6/11$217
This Frontier deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/107:15 pmRSW - MDW
1 stop5h 02mFrontier
Sun 7/136:20 amMDW - RSW
1 stop11h 01mFrontier
Deal found 6/11$234
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/116:50 amRSW - ORD
1 stop8h 10mSouthwest
Mon 7/147:00 amORD - RSW
1 stop10h 25mSouthwest
Deal found 6/10$262
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/288:00 amRSW - ORD
1 stop9h 12mSun Country Air
Sun 8/3110:43 amORD - RSW
1 stop9h 47mSun Country Air
Deal found 6/10$270
This FlightHub deal was found by Cheapflights users on 6/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/147:15 pmRSW - ORD
1 stop6h 07mFrontier
Sun 8/175:01 amORD - RSW
1 stop12h 20mFrontier
Deal found 6/12$276

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 June 12, 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 7/10

9:34 pm-11:44 pm

Nonstop3h 10m

Chicago O'Hare Intl

Thu 7/17

8:55 am-12:48 pm

Nonstop2h 53m

$148

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Wed 8/27

12:28 pm-2:43 pm

Nonstop3h 15m

Chicago O'Hare Intl

Wed 8/27

4:20 pm-8:18 pm

Nonstop2h 58m

$152

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 8/23

4:25 pm-6:15 pm

Nonstop2h 50m

Chicago Midway

Tue 8/26

9:05 am-12:50 pm

Nonstop2h 45m

$157

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 8/14

3:38 pm-5:55 pm

Nonstop3h 17m

Chicago O'Hare Intl

Sun 8/17

10:49 am-2:45 pm

Nonstop2h 56m

$159

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 7/10

7:15 pm-12:22 am

1 stop6h 07m

Chicago O'Hare Intl

Tue 7/15

4:34 pm-8:29 pm

Nonstop2h 55m

$195

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 8/21

6:15 pm-11:56 pm

1 stop6h 41m

Chicago O'Hare Intl

Sat 8/23

7:10 am-3:16 pm

1 stop7h 06m

$217

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 7/10

5:45 pm-9:42 pm

1 stop4h 57m

Chicago Midway

Tue 7/15

10:30 am-4:40 pm

1 stop5h 10m

$217

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 7/10

7:15 pm-11:17 pm

1 stop5h 02m

Chicago Midway

Sun 7/13

6:20 am-6:21 pm

1 stop11h 01m

$234

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 7/11

6:50 am-2:00 pm

1 stop8h 10m

Chicago O'Hare Intl

Mon 7/14

7:00 am-6:25 pm

1 stop10h 25m

$262

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 8/28

8:00 am-4:12 pm

1 stop9h 12m

Chicago O'Hare Intl

Sun 8/31

10:43 am-9:30 pm

1 stop9h 47m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 26 results
1
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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
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
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
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
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
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
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 June 9, 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 June 12, 2025.

It’s typically best to fly out from Fort Myers to Chicago in the evening. Doing so could potentially save you 37% on the flight price compared to flying in the morning, 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 June 8, 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 June 12, 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 (10 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Fort Myers to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

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.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

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
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

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.
JetBlue
7.3
Good
2,925 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

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
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

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.

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

    Our cheapest airline available from Fort Myers to Chicago is Spirit Airlines. Our recent data shows that you can find tickets from as low as $148 on this airline. Additional options worth looking into are United Airlines and Southwest, starting at $152 and $157 round-trip. You may be able to fly from Fort Myers to Chicago for 37% 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 Southwest, which is currently one of the cheapest options available, starting at $89. United Airlines flights start at $90 while deals on Spirit Airlines start at $93 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 Emirates (97%), SWISS (93%) and Alaska Airlines (86%).

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

    On average you can expect to pay $1,450 for a flight from Fort Myers to Chicago. The cheapest flight overall is $77 while the most popular route, (Fort Myers SW Florida Intl - Chicago O'Hare Intl) is currently priced at $108.

  • 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 Fort Myers?

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

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$131FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$70Average$164FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$159Average$270FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$159Average$335FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$210Average$394FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$367FlexibilityNo cancel feeOn-timeN/A

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