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$135+ Cheap flights from Cancún (CUN) 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
CUN — CHI
ene. 14 — ene. 211
mié. 1/14
mié. 1/21
1 adult, Economy
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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”

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Cheapflights Tip: The best prices from Cancun to Chicago are usually found in January or February, booked 77 days in advance, depart on a Friday or Sunday and return on a Monday

Cheap flight deals from Cancún to Chicago

Cheapest flights from Cancún to Chicago
Explore the most affordable flight options available from Cancún to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/15. 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.
jue. 12/2511:50 amCUN - ORD
Nonstop4h 03mSpirit Airlines
lun. 1/56:05 amORD - CUN
Nonstop3h 50mSpirit Airlines
Deal found 12/15$225
This Super.com deal was found by Cheapflights users on 12/13. 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.
lun. 12/2211:50 amCUN - ORD
Nonstop4h 03mSpirit Airlines
lun. 1/56:05 amORD - CUN
Nonstop3h 50mSpirit Airlines
Deal found 12/13$226
This Cheapflightsfares deal was found by Cheapflights users on 12/13. 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.
sáb. 12/2011:50 amCUN - ORD
Nonstop4h 03mSpirit Airlines
dom. 1/46:05 amORD - CUN
Nonstop3h 50mSpirit Airlines
Deal found 12/13$232
This Cheapflightsfares deal was found by Cheapflights users on 12/13. 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.
vie. 12/2611:50 amCUN - ORD
Nonstop4h 03mSpirit Airlines
lun. 1/55:00 amORD - CUN
1 stop7h 31mSpirit Airlines
Deal found 12/13$245
This American Airlines deal was found by Cheapflights users on 12/14. 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.
sáb. 12/202:34 pmCUN - ORD
Nonstop4h 05mAmerican Airlines
dom. 1/46:40 amORD - CUN
1 stop7h 06mAmerican Airlines
Deal found 12/14$267
This United Airlines deal was found by Cheapflights users on 12/13. 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.
sáb. 12/278:15 amCUN - ORD
Nonstop3h 55mUnited Airlines
sáb. 1/33:57 pmORD - CUN
Nonstop3h 47mUnited Airlines
Deal found 12/13$273
This Delta deal was found by Cheapflights users on 12/13. 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.
lun. 12/228:00 amCUN - MDW
2 stops10h 26mDelta
lun. 1/56:45 amMDW - CUN
1 stop6h 18mDelta
Deal found 12/13$278
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/2512:05 pmCUN - MDW
2 stops11h 17mDelta
lun. 1/59:32 amMDW - CUN
2 stops10h 39mDelta
Deal found 12/15$279
This Frontier deal was found by Cheapflights users on 12/15. 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.
mar. 12/302:50 pmCUN - MDW
1 stop8h 22mFrontier
lun. 1/56:12 amMDW - CUN
1 stop6h 28mFrontier
Deal found 12/15$332
This FlightHub deal was found by Cheapflights users on 12/13. 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.
lun. 12/292:50 pmCUN - MDW
1 stop8h 22mFrontier
sáb. 1/36:12 amMDW - CUN
1 stop6h 25mFrontier
Deal found 12/13$338
This Orbitz deal was found by Cheapflights users on 12/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/302:50 pmCUN - MDW
1 stop8h 22mFrontier
dom. 1/410:50 pmMDW - CUN
1 stop17h 22mFrontier
Deal found 12/14$339
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/151:33 pmCUN - MDW
1 stop11h 14mDelta
jue. 12/186:00 amMDW - CUN
1 stop8h 33mDelta
Deal found 12/15$354

Find flight deals from Cancún to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Cancún (CUN) 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 diciembre 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$173
(Frontier)

One-way from

$135
(Cheapflightsfares)

Popular in

September

Cheapest in

January

Average price

$271

Good round-trip deal

$178 or less

Good one-way deal

$178 or less
Provider with most accurate pricing for Cancun-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Cancun-Chicago (CHI) flights.
Search Deals
From Cancun to Chicago (CHI)
Search Deals
One-way flight from Cancun to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Cancun to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Cancun to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cancún 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 diciembre 15, 2025.
Use the filters below to find and compare flights from Cancún to Chicago that are best for you.

Fly from

Cancún

Fly to

Chicago

Route

Depart

Return

Price

CancúnChicago

CUN - ORD

CUNORD

Cancun

vie. 1/23

11:59 am-2:53 pm

Nonstop3h 54m

Chicago O'Hare Intl

vie. 1/30

6:05 am-10:54 am

Nonstop3h 49m

$209

CancúnChicago

CUN - ORD

CUNORD

Cancun

jue. 1/22

1:27 pm-4:27 pm

Nonstop4h 00m

Chicago O'Hare Intl

lun. 1/26

7:50 pm-12:54 pm

1 stop16h 04m

$221

CancúnChicago

CUN - ORD

CUNORD

Cancun

mié. 1/21

3:18 pm-6:09 pm

Nonstop3h 51m

Chicago O'Hare Intl

lun. 1/26

7:00 am-3:45 pm

1 stop7h 45m

$221

CancúnChicago

CUN - ORD

CUNORD

Cancun

jue. 1/15

3:18 pm-6:09 pm

Nonstop3h 51m

Chicago O'Hare Intl

mar. 1/27

7:34 am-12:30 pm

Nonstop3h 56m

$221

CancúnChicago

CUN - ORD

CUNORD

Cancun

vie. 1/16

1:27 pm-4:27 pm

Nonstop4h 00m

Chicago O'Hare Intl

mar. 1/27

10:35 am-3:35 pm

Nonstop4h 00m

$221

CancúnChicago

CUN - ORD

CUNORD

Cancun

vie. 1/23

3:18 pm-6:09 pm

Nonstop3h 51m

Chicago O'Hare Intl

lun. 1/26

7:34 am-12:30 pm

Nonstop3h 56m

$221

CancúnChicago

CUN - ORD

CUNORD

Cancun

mié. 2/11

4:47 pm-7:47 pm

Nonstop4h 00m

Chicago O'Hare Intl

dom. 2/15

9:15 pm-11:25 am

1 stop13h 10m

$221

CancúnChicago

CUN - MDW

CUNMDW

Cancun

jue. 1/22

1:45 pm-4:30 pm

Nonstop3h 45m

Chicago Midway

lun. 1/26

9:15 am-1:55 pm

Nonstop3h 40m

$272

CancúnChicago

CUN - MDW

CUNMDW

Cancun

mié. 2/4

4:40 pm-10:22 pm

1 stop6h 42m

Chicago Midway

lun. 2/9

6:00 am-2:03 pm

1 stop7h 03m

$278

CancúnChicago

CUN - MDW

CUNMDW

Cancun

vie. 1/23

8:00 am-5:29 pm

1 stop10h 29m

Chicago Midway

vie. 1/30

6:00 am-3:30 pm

1 stop8h 30m

$278

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 38 results
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Compare providers for flights from Cancún to Chicago

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 Cancún to Chicago in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars

*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 Cancún-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Cancún-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Cancún-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Cancún-Chicago 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 Cancún-Chicago 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 Cancún to Chicago

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

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

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

The price you pay for your flight from Cancún to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 77 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 Cancún to Chicago?

Currently, August is the cheapest month in which you can book a flight from Cancún to Chicago (average of $78). Flying from Cancún to Chicago in June is currently the most expensive (average of $254). 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 CUN to CHI?

Find hourly flight availability from Cancún 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 diciembre 15, 2025.

It’s optimal to fly from Cancún to Chicago in the evening. By choosing this option you can save up to 66% on the cost of your flight, compared to a flight in the afternoon.

Weekly flight availability from Cancún to Chicago

Explore weekly flight availability from Cancún 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 diciembre 15, 2025.

The most flights from CUN to CHI are scheduled on a Friday (11 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (5 on average).

How often are flights from Cancún to Chicago delayed?

About 11% of weekly flights between Cancún and Chicago have experienced delays in the past year, with the average delay time being 155 minutes.

What is the most punctual flight time for Cancún to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Cancún to Chicago flights?

Over the last year, Southwest have had the lowest number of delays on this route, with just 8% of flights being delayed.

The best insider tips for Cancún to Chicago 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 Cancún to Chicago trip
Airlines
Spirit Airlines

Spirit's Big Front Seats offer 11 extra inches of legroom, ideal for added comfort.


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

Read more about Spirit AirlinesBy Daniel Scheffler
United Airlines

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


United's Polaris Business Class features lie-flat seats and upscale amenities for premium comfort.

Read more about United AirlinesBy Harriet Baskas
Frontier

Frontier's UpFront Plus guarantees an empty middle seat for extra comfort.


Frontier's Economy Bundle includes a carry-on, seat selection, and no change fees.

Read more about FrontierBy Marisa Garcia
Airports
CUN

Check your departure terminal at CUN; terminals aren't connected. A bus runs every ten minutes between them.

Read more about CUNBy Ramsey Qubein
ORD

For international arrivals at ORD, expect long walks to immigration in Terminal 5. No moving walkways available.

Read more about ORDBy 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 Frontier

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 CUN

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

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 diciembre 15, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and Spirit Airlines from Cancún to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,249 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,249 reviews
Southwest
7.9
Good
4,249 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,092 reviews
Southwest
7.9
Good
4,249 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,187 reviews
Southwest
7.9
Good
4,249 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,080 reviews
Southwest
7.9
Good
4,249 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Cancún 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 Cancún to Chicago?

    Most people fly from Cancun (CUN) if they book a flight from Cancún to Chicago. On average, Cancun has 9 outbound flights to Chicago per day from 4 airlines. Cancun is conveniently located just 8.9 mi from Cancún’s city center.

  • How long is the flight from Cancún to Chicago?

    For as low as $272, Spirit Airlines can have you in Chicago from Cancún in 3h 45m. Cancún and Chicago are separated by a distance of 1434 mi. Generally, flights for this route are nonstop.

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

    Frontier, at $142, was found to be the cheapest airline from Cancún to Chicago.Alternate airlines to your destination round-trip include Spirit Airlines and United Airlines. Users have found that Frontier is 50% cheaper than the other options available to this destination.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $107. Spirit Airlines flights start at $112 while deals on United Airlines start at $139 one-way.

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

    No one likes to see their flight delayed. When booking a flight from Cancún to Chicago consider choosing Qatar Airways (88%), Frontier (83%) or American Airlines (82%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Cancún to Chicago?

    On average you can expect to pay $254 for a flight from Cancún to Chicago. The cheapest flight overall is $127 while the most popular route, (Cancun - Chicago O'Hare Intl) is currently priced at $197.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Cancún to Chicago (average of $78). Flying from Cancún to Chicago in June is currently the most expensive (average of $254). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Cancún to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Cancún to O'Hare Intl flights
Cozumel to O'Hare Intl flights
Cancún to Midway flights
Cancún to St. Louis flights
Cozumel to St. Louis flights

Top 4 airlines flying from Cancún to Chicago

Discover the top 4 airlines that operate flights from Cancún 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 diciembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$142Average$198FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$194Average$292FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$209Average$328FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$271Average$352FlexibilityNo cancel feeOn-time71%

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