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Puerto Rico

$105+ Cheap flights from New Haven (HVN) to Puerto Rico

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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Find flight deals from New Haven to Puerto Rico

Cheapest flights from New Haven to Puerto Rico
Explore the most affordable flight options available from New Haven to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/152:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Thu 11/203:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 10/28$200
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.
Sun 11/238:49 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Tue 11/253:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 10/28$206
This CheapOair deal was found by Cheapflights users on 10/27. 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.
Sat 11/152:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Sun 11/233:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 10/27$211
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.
Sat 11/152:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Sat 11/221:24 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 10/28$235
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.
Wed 11/122:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Tue 11/253:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 10/28$259
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/122:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Wed 11/191:24 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 10/28$260
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/166:30 amHVN - SJU
1 stop9h 49mMultiple Airlines
Thu 11/203:44 amSJU - HVN
Nonstop4h 01mMultiple Airlines
Deal found 10/28$270
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/152:00 pmHVN - SJU
Nonstop3h 54mMultiple Airlines
Fri 11/2111:55 amSJU - HVN
2 stops25h 28mMultiple Airlines
Deal found 10/28$275
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.
Sat 11/82:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Sat 11/157:54 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 10/28$276
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/152:00 pmHVN - SJU
Nonstop3h 54mMultiple Airlines
Sat 11/228:33 pmSJU - HVN
2 stops20h 22mMultiple Airlines
Deal found 10/28$280

Cheap flight deals from New Haven to Puerto Rico

Keep the following information in mind while searching for New Haven to Puerto Rico flight deals. Data was last updated October 29, 2025.

Round-trip from

$200
(Mytrip)

One-way from

$105
(CheapOair)

Popular in

December

Cheapest in

March

Average price

$218

Good round-trip deal

$241 or less

Good one-way deal

$159 or less
From Tweed-New Haven to Puerto Rico
Search Deals
One-way flight from Tweed-New Haven to Puerto Rico
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Tweed-New Haven to Puerto Rico.
Search Deals
Price to beat on a one-way flight from Tweed-New Haven to Puerto Rico.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from New Haven to Puerto Rico 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 October 29, 2025.
Use the filters below to find and compare flights from New Haven to Puerto Rico that are best for you.

Fly from

New Haven

Fly to

Puerto Rico

Route

Depart

Return

Price

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 2/21

6:30 am-11:20 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 2/25

12:20 pm-3:25 pm

Nonstop4h 05m

$257

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sun 11/16

6:30 am-5:19 pm

1 stop9h 49m

San Juan Luis Munoz Marin Intl

Thu 11/20

3:44 am-6:45 am

Nonstop4h 01m

$270

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 11/15

2:00 pm-6:54 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Fri 11/21

11:55 am-12:23 pm

2 stops25h 28m

$275

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 11/8

2:00 pm-6:54 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Sat 11/15

7:54 pm-10:55 pm

Nonstop4h 01m

$276

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 11/15

2:00 pm-6:54 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Sat 11/22

8:33 pm-3:55 pm

2 stops20h 22m

$280

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 11/19

7:30 am-12:24 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Tue 11/25

3:44 am-6:45 am

Nonstop4h 01m

$295

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 2/20

2:25 pm-4:39 am

2 stops13h 14m

San Juan Luis Munoz Marin Intl

Wed 2/25

12:20 pm-3:25 pm

Nonstop4h 05m

$298

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 2/21

4:00 pm-9:52 am

1 stop16h 52m

San Juan Luis Munoz Marin Intl

Wed 2/25

12:20 pm-3:25 pm

Nonstop4h 05m

$313

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sun 11/23

8:49 pm-1:43 am

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Sun 11/30

3:44 am-6:45 am

Nonstop4h 01m

$317

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 1/30

1:55 pm-6:53 pm

Nonstop3h 58m

$105

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 19 results
1
2

Best time to book a flight from New Haven to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from New Haven 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 New Haven to Puerto Rico

What is the cheapest month to book a flight from New Haven to Puerto Rico?

Currently, February is the cheapest month in which you can book a flight from New Haven to Puerto Rico (average of $52). Flying from New Haven to Puerto Rico in August is currently the most expensive (average of $132). 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 HVN to PR?

Find hourly flight availability from New Haven to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 29, 2025.

It’s optimal to fly from New Haven to Puerto Rico in the afternoon. By choosing this option you can save up to 17% on the cost of your flight, compared to a flight at noon.

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated October 29, 2025.
Read reviews from past customers who have flown Avelo Airlines, JetBlue, and Frontier from New Haven to Puerto Rico. 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.
Avelo Airlines
7.5
Good

Boarding

7.7

Overall

7.5

Food

5.0

Comfort

7.1

Crew

8.2

Entertainment

5.0

Reviews

1 / 6
2.0
Mediocre

Cindy,Sep 2023

MCO - DAY

I was emailed and told that if I check my luggage early I get a 10 dollar discount, also on the website, if it's under 50 lbs. it would be $40.00 I was charged $65.00 on first flight and $60.00 on second flight (second flight I checked in early, did not receive the discount, both flights my luggage was under 40 lbs.). Avelo destroyed my luggage, wheels were tore off, and plastic was ripped off.
Avelo Airlines
7.5
Good
Avelo Airlines
7.5
Good

Boarding

7.7

Overall

7.5

Food

5.0

Comfort

7.1

Crew

8.2

Entertainment

5.0

Reviews

1 / 6
2.0
Mediocre

Cindy,Sep 2023

MCO - DAY

I was emailed and told that if I check my luggage early I get a 10 dollar discount, also on the website, if it's under 50 lbs. it would be $40.00 I was charged $65.00 on first flight and $60.00 on second flight (second flight I checked in early, did not receive the discount, both flights my luggage was under 40 lbs.). Avelo destroyed my luggage, wheels were tore off, and plastic was ripped off.
JetBlue
7.2
Good
2,906 reviews
Avelo Airlines
7.5
Good

Boarding

7.7

Overall

7.5

Food

5.0

Comfort

7.1

Crew

8.2

Entertainment

5.0

Reviews

1 / 6
2.0
Mediocre

Cindy,Sep 2023

MCO - DAY

I was emailed and told that if I check my luggage early I get a 10 dollar discount, also on the website, if it's under 50 lbs. it would be $40.00 I was charged $65.00 on first flight and $60.00 on second flight (second flight I checked in early, did not receive the discount, both flights my luggage was under 40 lbs.). Avelo destroyed my luggage, wheels were tore off, and plastic was ripped off.
Frontier
5.8
Fair
3,123 reviews
Avelo Airlines
7.5
Good

Boarding

7.7

Overall

7.5

Food

5.0

Comfort

7.1

Crew

8.2

Entertainment

5.0

Reviews

1 / 6
2.0
Mediocre

Cindy,Sep 2023

MCO - DAY

I was emailed and told that if I check my luggage early I get a 10 dollar discount, also on the website, if it's under 50 lbs. it would be $40.00 I was charged $65.00 on first flight and $60.00 on second flight (second flight I checked in early, did not receive the discount, both flights my luggage was under 40 lbs.). Avelo destroyed my luggage, wheels were tore off, and plastic was ripped off.

Related info for your journey

Find useful and relevant information for your journey from New Haven to Puerto Rico. 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 New Haven to Puerto Rico?

    Tweed-New Haven (HVN), located 3.6 mi from the city center, is the airport you fly out of when you book flights from New Haven to Puerto Rico.

  • How long is the flight from New Haven to Puerto Rico?

    A quick flight from New Haven to Puerto Rico can take about 3h 50m. Avelo Airlines provides one of the quickest options available for as low as $257. Airlines will cover a distance of 1628 mi. All flights are typically nonstop.

  • What are the cheapest flights from New Haven to Puerto Rico?

    Looking at all options, your cheapest flight can be booked for $113. While the most popular route (Tweed-New Haven - San Juan Luis Munoz Marin Intl) can be booked for $203 on average, our data indicates $269 when flying from New Haven to Puerto Rico.

  • Can I find deals for flights from New Haven to Puerto Rico that include hotel bookings?

    Yes. In addition to deals on New Haven to Puerto Rico flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from New Haven to Puerto Rico?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New Haven to Puerto Rico.

  • Can I find deals for business class flights from New Haven to Puerto Rico?

    Yes. Cheapflights offers flight deals from New Haven to Puerto Rico 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 New Haven to Puerto Rico?

    Currently, February is the cheapest month in which you can book a flight from New Haven to Puerto Rico (average of $52). Flying from New Haven to Puerto Rico in August is currently the most expensive (average of $132). 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 New Haven to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from New Haven to Puerto Rico

Discover the top 3 airlines that operate flights from New Haven to Puerto Rico. 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$211FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$186Average$315FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$196Average$287FlexibilityNo cancel feeOn-timeN/A

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