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$61+ Cheap flights from Chicago (CHI) to Sarasota (SRQ)

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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SRQ
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago to Sarasota Bradenton Intl are usually found in January or February, booked 46 days in advance, depart on a Monday or Wednesday and return on a Friday

Cheap flight deals from Chicago to Sarasota

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Sarasota (SRQ). 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 octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$227
(Kiwi.com)

One-way from

$61
(CheapOair)

Popular in

November

Cheapest in

January

Average price

$397

Good round-trip deal

$147 or less

Good one-way deal

$91 or less
Provider with most accurate pricing for Chicago (CHI)-Sarasota Bradenton Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Sarasota Bradenton Intl flights.
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From Chicago (CHI) to Sarasota Bradenton Intl
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One-way flight from Chicago (CHI) to Sarasota Bradenton Intl
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Highest demand for flights based on searches. 16% potential increase in price ($75 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Sarasota Bradenton Intl.
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Price to beat on a one-way flight from Chicago (CHI) to Sarasota Bradenton Intl.
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Find flight deals from Chicago to Sarasota

Cheapest flights from Chicago to Sarasota
Explore the most affordable flight options available from Chicago to Sarasota. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/145:11 amORD - SRQ
1 stop13h 43mMultiple Airlines
lun. 12/2211:41 amSRQ - ORD
1 stop13h 13mMultiple Airlines
Deal found 10/30$227
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/75:35 pmMDW - SRQ
1 stop17h 07mAllegiant Air
vie. 11/146:01 amSRQ - MDW
1 stop9h 36mAllegiant Air
Deal found 10/28$227
This CheapOair deal was found by Cheapflights users on 10/28. 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.
jue. 10/308:26 amORD - SRQ
1 stop10h 17mFrontier
dom. 11/28:30 pmSRQ - ORD
1 stop11h 56mFrontier
Deal found 10/28$228
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/53:14 pmORD - SRQ
1 stop6h 48mMultiple Airlines
mié. 12/108:20 amSRQ - ORD
2 stops29h 48mMultiple Airlines
Deal found 10/28$234
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/145:11 amORD - SRQ
1 stop13h 43mMultiple Airlines
jue. 12/2512:17 pmSRQ - ORD
1 stop29h 25mMultiple Airlines
Deal found 10/30$235
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/156:11 amORD - SRQ
2 stops15h 51mMultiple Airlines
jue. 12/2512:17 pmSRQ - ORD
1 stop29h 25mMultiple Airlines
Deal found 10/28$236
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/145:11 amORD - SRQ
1 stop13h 43mMultiple Airlines
dom. 12/2111:53 amSRQ - ORD
1 stop22h 57mMultiple Airlines
Deal found 10/30$238
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/2810:00 amORD - SRQ
1 stop12h 02mMultiple Airlines
vie. 12/51:12 pmSRQ - ORD
2 stops23h 42mMultiple Airlines
Deal found 10/30$239
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/411:44 amORD - SRQ
2 stops34h 18mMultiple Airlines
jue. 12/1112:38 pmSRQ - ORD
1 stop22h 38mMultiple Airlines
Deal found 10/29$240
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/145:11 amORD - SRQ
1 stop13h 43mMultiple Airlines
mié. 12/2411:10 amSRQ - ORD
2 stops28h 52mMultiple Airlines
Deal found 10/30$241
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/75:35 pmMDW - SRQ
1 stop17h 07mAllegiant Air
dom. 11/95:58 pmSRQ - MDW
1 stop19h 04mAllegiant Air
Deal found 10/30$241
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/75:35 pmMDW - SRQ
1 stop17h 07mAllegiant Air
dom. 11/165:58 pmSRQ - MDW
1 stop19h 04mAllegiant Air
Deal found 10/29$249

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Sarasota 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 octubre 30, 2025.
Use the filters below to find and compare flights from Chicago to Sarasota that are best for you.

Fly from

Chicago

Fly to

Sarasota

Route

Depart

Return

Price

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

mié. 2/18

11:00 am-3:00 pm

Nonstop3h 00m

Sarasota Bradenton Intl

mar. 2/24

4:06 pm-6:26 pm

Nonstop3h 20m

$279

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

sáb. 12/13

11:05 am-2:58 pm

Nonstop2h 53m

Sarasota Bradenton Intl

jue. 12/25

12:23 pm-2:35 pm

Nonstop3h 12m

$286

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

jue. 12/4

6:15 pm-10:00 pm

Nonstop2h 45m

Sarasota Bradenton Intl

lun. 12/8

11:35 am-1:25 pm

Nonstop2h 50m

$293

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

mié. 12/17

6:00 am-2:33 pm

1 stop7h 33m

Sarasota Bradenton Intl

jue. 12/25

3:58 pm-9:34 pm

1 stop6h 36m

$299

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

jue. 12/4

5:30 am-12:27 pm

1 stop5h 57m

Sarasota Bradenton Intl

lun. 12/8

1:32 pm-6:43 pm

1 stop6h 11m

$299

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

lun. 12/8

5:29 pm-12:26 am

1 stop5h 57m

Sarasota Bradenton Intl

jue. 12/11

6:00 am-11:55 am

1 stop6h 55m

$299

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

jue. 2/26

5:15 pm-11:45 pm

1 stop5h 30m

Sarasota Bradenton Intl

mar. 3/3

12:05 pm-9:50 pm

2 stops10h 45m

$304

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

mar. 1/6

9:50 am-8:55 pm

2 stops10h 05m

Sarasota Bradenton Intl

sáb. 1/10

12:45 pm-6:35 pm

1 stop6h 50m

$311

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

jue. 2/19

1:45 pm-10:15 pm

2 stops7h 30m

Sarasota Bradenton Intl

mié. 2/25

12:05 pm-9:50 pm

2 stops10h 45m

$316

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

jue. 11/27

1:40 pm-5:15 pm

Nonstop2h 35m

Sarasota Bradenton Intl

jue. 12/4

11:35 am-1:25 pm

Nonstop2h 50m

$343

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 40 results
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Compare providers for flights from Chicago to Sarasota

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 Chicago to Sarasota in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
JustAirTicketPrice 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 Chicago-Sarasota flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Sarasota flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Sarasota flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Sarasota flights, Cheapflights users trust eDreams the most. eDreams 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 Chicago-Sarasota 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 Chicago to Sarasota

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Sarasota. Price data was last updated on October 24, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Sarasota, you should look to book at least 46 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Sarasota (average of $42). Flying from Chicago to Sarasota in October is currently the most expensive (average of $93). 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 CHI to SRQ?

Find hourly flight availability from Chicago to Sarasota. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated octubre 30, 2025.

It’s optimal to fly from Chicago to Sarasota at noon. By choosing this option you can save up to 60% on the cost of your flight, compared to a flight in the evening.

What is the cheapest day to fly from Chicago to Sarasota?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Sarasota. Price data was last updated on October 26, 2025.

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

The best insider tips for Chicago to Sarasota 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 Chicago to Sarasota trip
Airports
ORD

For a quick departure from ORD, consider using the 'L' train to avoid Chicago traffic delays.

Read more about ORDby Ramsey Qubein
SRQ

Use the Breeze shuttle for a direct link from SRQ to downtown Sarasota hotels, offering comfort and ample luggage space.

Read more about SRQby Brandon Schultz
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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
Brandon Schultz

Brandon Schultz

Expert on SRQ

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

Reviews of airlines servicing Sarasota

Get insights into the airlines that provide service to Sarasota. 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 Sarasota. Reviews last updated octubre 30, 2025.
Read through reviews of airlines operating flights from Chicago to Sarasota, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Delta
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.2
Good
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.8
Fair
3,122 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Sarasota. 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 into for flights to Sarasota from Chicago?

    Sarasota Bradenton Intl (SRQ) is the airport you will fly into if you book a flight from Chicago to Sarasota. You should not have trouble finding flights to Sarasota Bradenton Intl from Chicago; the airport handles an average of 2 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 6 airlines have flights to the Sarasota airport from Chicago. It is only a 4.3 mi journey from Sarasota Bradenton Intl (SRQ) to Sarasota’s city center.

  • How long is the flight from Chicago to Sarasota?

    United Airlines, Southwest, and Delta can get you from Chicago to Sarasota in just under 2h 45m. Your travel time can differ by up to 4h 48m. Airlines will cover a distance of 1036 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, Frontier ($37), Allegiant Air ($96), and Delta ($196) offers the cheapest pricing from Chicago to Sarasota. Frontier is 90% cheaper than the average price of flights available within the next 90 days to this destination.

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

    One-way options have recently been found by users for as low as $106 on JetBlue. Other airlines that offer cheap prices include Sun Country Air from $125 and United Airlines from $140 one-way.

  • What are the most reliable airlines from Chicago to Sarasota?

    Before booking your flight to Sarasota from Chicago, check out the most reliable airlines to get you to your destination on time: United Airlines (91%), Air Canada (82%), Emirates( 82%).

  • What are the cheapest flights from Chicago to Sarasota?

    While on average a flight from Chicago to Sarasota is generally $304, our data shows the cheapest flight currently is $156. When looking at the most popular route, (Chicago O'Hare Intl - Sarasota Bradenton Intl), you can expect to pay $176 for that flight.

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

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

  • How can I find direct flights from Chicago to Sarasota?

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

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

    Yes. Cheapflights offers flight deals from Chicago to Sarasota 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 Chicago to Sarasota?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Sarasota (average of $42). Flying from Chicago to Sarasota in October is currently the most expensive (average of $93). 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

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Alternative routes for Chicago to Sarasota

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

Discover the top 6 airlines that operate flights from Chicago to Sarasota. 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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$118FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$96Average$177FlexibilityNo cancel feeOn-time88%
DeltaCheapest$196Average$346FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$199Average$372FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$227Average$412FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$285Average$404FlexibilityNo cancel feeOn-time63%

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