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Punta Cana

$92+ Cheap flights from Chicago (CHI) to Punta Cana (PUJ)

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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
oct. 26 — nov. 21
dom. 10/26
dom. 11/2
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Punta Cana are usually found in August or July, booked 87 days in advance, depart on a Tuesday or Monday and return on a Sunday

Cheap flight deals from Chicago to Punta Cana

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Punta Cana (PUJ). 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 septiembre 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$320
(Cheapflightsfares)

One-way from

$92
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$477

Good round-trip deal

$391 or less

Good one-way deal

$126 or less
Provider with most accurate pricing for Chicago (CHI)-Punta Cana flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Punta Cana flights.
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From Chicago (CHI) to Punta Cana
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One-way flight from Chicago (CHI) to Punta Cana
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Highest demand for flights based on searches. 8% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Punta Cana.
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Price to beat on a one-way flight from Chicago (CHI) to Punta Cana.
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Find flight deals from Chicago to Punta Cana

Cheapest flights from Chicago to Punta Cana
Explore the most affordable flight options available from Chicago to Punta Cana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 26, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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. 10/307:43 pmORD - PUJ
1 stop18h 17mSpirit Airlines
mar. 11/41:52 pmPUJ - ORD
2 stops13h 11mSpirit Airlines
Deal found 9/24$320
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/79:47 pmORD - PUJ
2 stops12h 29mMultiple Airlines
sáb. 11/155:47 amPUJ - ORD
Nonstop5h 10mMultiple Airlines
Deal found 9/25$321
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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. 10/187:43 pmORD - PUJ
1 stop18h 06mSpirit Airlines
sáb. 10/2512:37 pmPUJ - ORD
2 stops12h 08mSpirit Airlines
Deal found 9/24$322
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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. 10/307:43 pmORD - PUJ
1 stop18h 17mSpirit Airlines
jue. 11/61:49 pmPUJ - ORD
2 stops11h 53mSpirit Airlines
Deal found 9/23$323
This Cheapflightsfares deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/17:43 pmORD - PUJ
1 stop19h 17mSpirit Airlines
jue. 11/61:49 pmPUJ - ORD
2 stops11h 53mSpirit Airlines
Deal found 9/26$324
This Cheapflightsfares deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/107:43 pmORD - PUJ
1 stop18h 06mSpirit Airlines
jue. 10/163:57 pmPUJ - ORD
1 stop8h 48mSpirit Airlines
Deal found 9/26$325
This Booking.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/116:58 pmORD - PUJ
1 stop15h 44mSpirit Airlines
jue. 10/163:57 pmPUJ - ORD
1 stop8h 48mSpirit Airlines
Deal found 9/25$326
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/75:05 amORD - PUJ
1 stop8h 44mSpirit Airlines
vie. 10/103:57 pmPUJ - ORD
1 stop19h 53mSpirit Airlines
Deal found 9/26$327
This United Airlines deal was found by Cheapflights users on 9/24. 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.
lun. 11/39:30 amORD - PUJ
Nonstop4h 32mUnited Airlines
sáb. 11/84:25 pmPUJ - ORD
Nonstop5h 13mUnited Airlines
Deal found 9/24$328
This Cheapflightsfares deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/272:14 pmORD - PUJ
2 stops20h 28mSpirit Airlines
sáb. 11/112:52 pmPUJ - ORD
2 stops13h 11mSpirit Airlines
Deal found 9/26$329
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/48:00 amORD - PUJ
1 stop26h 42mMultiple Airlines
vie. 10/103:57 pmPUJ - ORD
1 stop19h 53mMultiple Airlines
Deal found 9/26$330
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/35:17 pmORD - PUJ
1 stop17h 24mSpirit Airlines
vie. 10/103:57 pmPUJ - ORD
1 stop19h 53mSpirit Airlines
Deal found 9/26$331

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Punta Cana 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 septiembre 26, 2025.
Use the filters below to find and compare flights from Chicago to Punta Cana that are best for you.

Fly from

Chicago

Fly to

Punta Cana

Route

Depart

Return

Price

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

lun. 11/3

9:30 am-4:02 pm

Nonstop4h 32m

Punta Cana

sáb. 11/8

4:25 pm-7:38 pm

Nonstop5h 13m

$328

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

lun. 11/10

6:00 am-3:38 pm

1 stop7h 38m

Punta Cana

sáb. 11/15

3:40 pm-9:01 am

1 stop19h 21m

$337

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

lun. 11/10

6:00 am-3:38 pm

1 stop7h 38m

Punta Cana

mar. 11/18

2:38 pm-11:40 pm

1 stop11h 02m

$337

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 10/28

9:30 am-3:02 pm

Nonstop4h 32m

Punta Cana

mar. 11/4

2:55 pm-6:08 pm

Nonstop5h 13m

$342

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

mar. 11/11

5:34 pm-1:26 pm

2 stops17h 52m

Punta Cana

sáb. 11/15

2:57 pm-9:51 am

2 stops20h 54m

$342

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

jue. 11/13

8:02 pm-1:13 pm

1 stop15h 11m

Punta Cana

sáb. 11/15

2:57 pm-8:42 am

2 stops19h 45m

$342

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 11/11

1:29 pm-1:26 pm

2 stops21h 57m

Punta Cana

mar. 11/18

2:38 pm-10:30 pm

1 stop9h 52m

$342

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

sáb. 11/8

5:40 pm-1:26 pm

2 stops17h 46m

Punta Cana

sáb. 11/15

3:40 pm-8:30 am

1 stop18h 50m

$342

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

lun. 11/10

5:56 pm-1:26 pm

2 stops17h 30m

Punta Cana

sáb. 11/15

2:57 pm-8:42 am

2 stops19h 45m

$342

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mar. 10/21

6:00 am-3:25 pm

1 stop8h 25m

Punta Cana

mar. 10/28

1:55 pm-6:08 pm

Nonstop5h 13m

$345

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/25

Showing 1-10 of 41 results
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Compare providers for flights from Chicago to Punta Cana

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 Punta Cana in September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust 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-Punta Cana flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Punta Cana flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Punta Cana flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Punta Cana flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Punta Cana flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

The best insider tips for Chicago to Punta Cana 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 Punta Cana trip
Airports
ORD

For a smooth departure from ORD, consider taking the “L” train to avoid Chicago traffic delays.

Read more about ORDby Ramsey Qubein
PUJ

At PUJ, immigration is swift, often under 20 minutes, making arrivals efficient.

Read more about PUJby Matt Meltzer
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
Matt Meltzer

Matt Meltzer

Expert on PUJ

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 Chicago to Punta Cana

Have a flexible travel schedule? Discover the best time to fly to Punta Cana 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 Punta Cana

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Punta Cana. Price data was last updated on September 19, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Punta Cana, you should look to book at least 87 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 Punta Cana?

Currently, January is the cheapest month in which you can book a flight from Chicago to Punta Cana (average of $443). Flying from Chicago to Punta Cana in June is currently the most expensive (average of $591). 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 PUJ?

Find hourly flight availability from Chicago to Punta Cana. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 26, 2025.

One of the essential ways to save on airfare from Chicago to Punta Cana is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 38% on airfare.

What is the cheapest day to fly from Chicago to Punta Cana?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Punta Cana. Price data was last updated on September 21, 2025.

Travelers seeking maximum savings on their Chicago to Punta Cana flight should consider departing on Monday at noon when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

What’s the top layover airport for flights from Chicago to Punta Cana?

Share of 1-stop round-trip flights from Chicago to Punta Cana chosen by Cheapflights users in the past 12 months, using the same layover each way.

Panama City (PTY) – chosen by Cheapflights users on 43% of 1-stop itineraries from Chicago to Punta Cana on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Punta Cana?

Average round-trip fare for 1-stop flights from Chicago to Punta Cana, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Fort Lauderdale (FLL) is the most affordable 1-stop option, with an average round-trip price of $231.

What’s the fastest layover option from Chicago to Punta Cana?

Shortest average travel time for 1-stop one-way flights from Chicago to Punta Cana, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Fort Lauderdale (FLL) have the shortest average one-way travel time for 1-stop routes: 6h 50m.

Which airport typically offers the quickest layover for flights from Chicago to Punta Cana?

Average layover duration for 1-stop one-way flights from Chicago to Punta Cana, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Baltimore (BWI) offer the fastest connection on this route, with an average layover time of 2h 00m.

Reviews of airlines servicing Punta Cana

Get insights into the airlines that provide service to Punta Cana. 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 Punta Cana. Reviews last updated septiembre 26, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines from Chicago to Punta Cana 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
4,245 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,926 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,161 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Chicago to Punta Cana. 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 Punta Cana from Chicago?

    If you book a flight to Punta Cana from Chicago, you will be flying to Punta Cana, which is the city’s only airport. Punta Cana (PUJ) is located 9.2 mi from the center of Punta Cana. There are 0 flights from Chicago to Punta Cana per day from 10 different airlines.

  • How long is the flight from Chicago to Punta Cana?

    Airlines like United Airlines and Delta fly from Chicago to Punta Cana in about 4h 32m. The time it takes to get you to your destination can typically vary by up to 3h 06m. The distance from Chicago to Punta Cana is about 1982 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Flying on WorldTicket is currently your cheapest option to Punta Cana, with prices starting at $173. Additional round-trip tickets that might be worth considering are offered by Frontier and Spirit Airlines, with the lowest prices starting at $224 and $231, respectively. WorldTicket is 67% 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 Punta Cana one-way?

    For one-way options, check prices for Arajet. According to our data, you can fly for as low as $116. Users have also found prices from $118 and $159 on Spirit Airlines and Frontier, respectively.

  • What are the most reliable airlines from Chicago to Punta Cana?

    Before booking your flight to Punta Cana from Chicago, check out the most reliable airlines to get you to your destination on time: American Airlines (83%), United Airlines (76%), Frontier( 52%).

  • What are the cheapest flights from Chicago to Punta Cana?

    Looking for the cheapest flight from Chicago to Punta Cana? While on average our users pay $724, our data indicates the cheapest price to be $115. The most popular route (Chicago O'Hare Intl - Punta Cana), is priced around $205.

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

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

  • How can I find direct flights from Chicago to Punta Cana?

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

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

    Yes. Cheapflights offers flight deals from Chicago to Punta Cana 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 Punta Cana?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Punta Cana (average of $443). Flying from Chicago to Punta Cana in June is currently the most expensive (average of $591). 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 Punta Cana?

Book flights to Punta Cana if you plan to visit one of these locations
Bavaro

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Top 9 airlines flying from Chicago to Punta Cana

Discover the top 9 airlines that operate flights from Chicago to Punta Cana. 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 septiembre 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$224Average$434FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$231Average$354FlexibilityNo cancel feeOn-time65%
ArajetCheapest$232Average$318FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$335Average$700FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$341Average$614FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$353Average$579FlexibilityNo cancel feeOn-time71%
DeltaCheapest$374Average$758FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$495Average$743FlexibilityNo cancel feeOn-time63%
AviancaCheapest$615Average$1,422FlexibilityNo cancel feeOn-time71%

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