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Punta Cana

$96+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PUJ
Aug 16 — Aug 231
Sat 8/16
Sat 8/23
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Punta Cana are usually found in July or August, booked 87 days in advance, depart on a Tuesday or Monday and return on a Saturday

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 August 11, 2025.

Round-trip from

$306
(Mytrip)

One-way from

$102
(FlightHub)

Popular in

March

Cheapest in

July

Average price

$485

Good round-trip deal

$377 or less

Good one-way deal

$126 or less
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. 2% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 11, 2025.

This Mytrip deal was found by Cheapflights users on 8/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/95:05 amORD - PUJ
1 stop8h 09mSpirit Airlines
Sat 9/133:19 pmPUJ - ORD
2 stops20h 23mSpirit Airlines
Deal found 8/11$306
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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.
Tue 10/75:05 amORD - PUJ
1 stop8h 09mSpirit Airlines
Tue 10/1412:36 pmPUJ - ORD
2 stops12h 09mSpirit Airlines
Deal found 8/10$307
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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.
Sat 12/610:27 amORD - PUJ
Nonstop4h 45mArajet
Sat 12/135:47 amPUJ - ORD
Nonstop5h 10mArajet
Deal found 8/10$308
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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.
Sat 9/66:44 pmORD - PUJ
1 stop18h 30mSpirit Airlines
Sat 9/133:19 pmPUJ - ORD
1 stop8h 29mSpirit Airlines
Deal found 8/10$309
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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 8/146:45 amORD - PUJ
Nonstop4h 40mFrontier
Sat 8/165:08 pmPUJ - ORD
Nonstop5h 08mFrontier
Deal found 8/10$310
This Gotogate deal was found by Cheapflights users on 8/10. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/186:45 amORD - PUJ
Nonstop4h 40mMultiple Airlines
Wed 8/274:05 pmPUJ - ORD
1 stop8h 54mMultiple Airlines
Deal found 8/10$311
This Expedia deal was found by Cheapflights users on 8/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/115:05 amORD - PUJ
1 stop8h 09mSpirit Airlines
Tue 10/143:19 pmPUJ - ORD
1 stop9h 26mSpirit Airlines
Deal found 8/10$313
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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.
Fri 10/35:17 pmORD - PUJ
1 stop17h 24mSpirit Airlines
Wed 10/83:19 pmPUJ - ORD
1 stop9h 26mSpirit Airlines
Deal found 8/10$317
This Spirit deal was found by Cheapflights users on 8/11. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/205:05 amORD - PUJ
1 stop8h 09mSpirit Airlines
Sat 10/253:19 pmPUJ - ORD
1 stop9h 26mSpirit Airlines
Deal found 8/11$318
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/163:30 amORD - PUJ
Nonstop4h 45mArajet
Tue 11/257:30 pmPUJ - ORD
Nonstop5h 10mArajet
Deal found 8/10$319
This Southwest deal was found by Cheapflights users on 8/10. 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.
Tue 9/96:25 amMDW - PUJ
1 stop6h 40mSouthwest
Tue 9/162:50 pmPUJ - MDW
1 stop7h 50mSouthwest
Deal found 8/10$343
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 10/278:05 pmMDW - PUJ
2 stops17h 05mSouthwest
Fri 10/311:40 pmPUJ - MDW
1 stop8h 30mSouthwest
Deal found 8/11$347

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 August 11, 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

Tue 9/9

5:05 am-2:14 pm

1 stop8h 09m

Punta Cana

Sat 9/13

3:19 pm-10:42 am

2 stops20h 23m

$306

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 10/7

5:05 am-2:14 pm

1 stop8h 09m

Punta Cana

Tue 10/14

12:36 pm-11:45 pm

2 stops12h 09m

$307

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 12/6

10:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sat 12/13

5:47 am-8:57 am

Nonstop5h 10m

$308

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 9/6

6:44 pm-2:14 pm

1 stop18h 30m

Punta Cana

Sat 9/13

3:19 pm-10:48 pm

1 stop8h 29m

$309

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 9/16

5:05 am-2:14 pm

1 stop8h 09m

Punta Cana

Wed 9/17

3:19 pm-11:10 am

2 stops20h 51m

$311

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 10/11

5:05 am-2:14 pm

1 stop8h 09m

Punta Cana

Tue 10/14

3:19 pm-11:45 pm

1 stop9h 26m

$313

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 10/3

5:17 pm-11:41 am

1 stop17h 24m

Punta Cana

Wed 10/8

3:19 pm-11:45 pm

1 stop9h 26m

$317

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 10/20

5:05 am-2:14 pm

1 stop8h 09m

Punta Cana

Sat 10/25

3:19 pm-11:45 pm

1 stop9h 26m

$318

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 11/16

3:30 am-10:15 am

Nonstop4h 45m

Punta Cana

Tue 11/25

7:30 pm-10:40 pm

Nonstop5h 10m

$319

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 8/27

5:05 am-3:00 pm

1 stop8h 55m

Punta Cana

Sat 8/30

4:05 pm-11:59 pm

1 stop8h 54m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/10

Showing 1-10 of 44 results
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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 August 8, 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 $593). 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 August 11, 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 39% 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 August 10, 2025.

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

Weekly flight availability from Chicago to Punta Cana

Explore weekly flight availability from Chicago to Punta Cana. 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 August 11, 2025.

The most flights from CHI to PUJ are scheduled on a Monday (3 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).

How much does it cost to fly round-trip from Chicago to Punta Cana?

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 August 11, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Copa 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
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,978 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Copa Airlines
7.5
Good
1,505 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,922 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 2 flights from Chicago to Punta Cana per day from 10 different airlines.

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

    Flying on Spirit Airlines is currently your cheapest option to Punta Cana, with prices starting at $306. Additional round-trip tickets that might be worth considering are offered by Arajet and Southwest, with the lowest prices starting at $308 and $343, respectively. Spirit Airlines is 43% 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 $96. Users have also found prices from $102 and $160 on Spirit Airlines and Delta, 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: United Airlines (85%), American Airlines (79%), Frontier( 61%).

  • 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 $681, our data indicates the cheapest price to be $155. The most popular route (Chicago O'Hare Intl - Punta Cana), is priced around $228.

  • 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 $593). 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 August 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$223Average$434FlexibilityNo cancel feeOn-time62%
ArajetCheapest$235Average$315FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$270Average$359FlexibilityNo cancel feeOn-time65%
Air CanadaCheapest$335Average$857FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$343Average$633FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$359Average$597FlexibilityNo cancel feeOn-time71%
DeltaCheapest$386Average$724FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$495Average$741FlexibilityNo cancel feeOn-time63%
AviancaCheapest$615Average$1,422FlexibilityNo cancel feeOn-time71%

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