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Puerto Rico

$111+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
Jun 29 — Jul 61
Mon 6/29
Mon 7/6
1 adult, Economy
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Cheap 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 May 30, 2026.

This Trip.com deal was found by Cheapflights users on 5/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:00 am
HVN
-
SJU
Nonstop3h 57m
Avelo Airlines
Mon 9/2112:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 5/27$221
This Super.com deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:30 am
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Fri 9/412:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 5/29$228
This Trip.com deal was found by Cheapflights users on 5/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:00 am
HVN
-
SJU
Nonstop3h 57m
Avelo Airlines
Mon 9/712:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 5/26$243
This CheapOair deal was found by Cheapflights users on 5/28. 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.
Mon 8/246:30 am
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Fri 9/412:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 5/28$250
This Super.com deal was found by Cheapflights users on 5/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:00 am
HVN
-
SJU
Nonstop3h 57m
Avelo Airlines
Mon 9/2812:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 5/25$251
This CheapOair deal was found by Cheapflights users on 5/28. 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.
Mon 8/316:30 am
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Fri 9/412:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 5/28$252
This CheapOair deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:00 am
HVN
-
SJU
Nonstop3h 57m
Avelo Airlines
Fri 9/1812:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 5/29$258
This CheapOair deal was found by Cheapflights users on 5/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:00 am
HVN
-
SJU
Nonstop3h 57m
Avelo Airlines
Mon 9/1412:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 5/25$266

Find 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 May 30, 2026.

Round-trip from

$221
(Trip.com)

One-way from

$170
(eDestinos)

Popular in

April

Cheapest in

October

Average price

$350

Good round-trip deal

$382 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. 12% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip 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 May 30, 2026.
Use the filters below to find and compare flights from New Haven to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Thu 9/3

6:31 pm-3:58 pm

2 stops21h 27m

San Juan Luis Munoz Marin Intl

Mon 9/7

12:08 pm-4:15 pm

Nonstop4h 07m

$375

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Thu 8/27

8:36 pm-8:09 am

1 stop11h 33m

San Juan Luis Munoz Marin Intl

Tue 9/1

4:05 pm-2:57 pm

1 stop22h 52m

$416

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 8/26

3:42 pm-11:29 pm

1 stop7h 47m

San Juan Luis Munoz Marin Intl

Mon 8/31

6:16 pm-2:02 pm

1 stop19h 46m

$422

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Thu 8/27

8:36 pm-8:09 am

1 stop11h 33m

San Juan Luis Munoz Marin Intl

Mon 8/31

6:16 pm-2:02 pm

1 stop19h 46m

$427

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 7/10

8:00 am-11:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Mon 8/31

11:30 am-3:27 pm

Nonstop3h 57m

$431
Quickest round-trip

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 7/4

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Mon 7/6

1:03 pm-4:55 pm

Nonstop3h 52m

$431

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Thu 8/27

8:36 pm-8:09 am

1 stop11h 33m

San Juan Luis Munoz Marin Intl

Sun 8/30

6:00 am-4:47 pm

2 stops10h 47m

$431

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 7/27

8:00 am-11:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 7/31

1:03 pm-4:55 pm

Nonstop3h 52m

$435

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 8/26

3:42 pm-6:26 am

2 stops14h 44m

San Juan Luis Munoz Marin Intl

Sat 8/29

6:00 am-2:57 pm

1 stop8h 57m

$436

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 7/13

6:55 pm-12:07 am

1 stop29h 12m

San Juan Luis Munoz Marin Intl

Thu 7/16

6:30 am-5:46 pm

1 stop11h 16m

$438

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/30

Showing 1-10 of 24 resultsSorted by cheapest first
1
2
3

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, March is the cheapest month in which you can book a flight from New Haven to Puerto Rico (average of $78). Flying from New Haven to Puerto Rico in September is currently the most expensive (average of $260). 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 May 30, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from New Haven to Puerto Rico as you normally would.

How far ahead should I book a flight from New Haven to Puerto Rico?

The price you pay for your flight from New Haven to Puerto Rico may vary depending on when you book. For the best chance of a lower fare, look to book 47 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 May 30, 2026.
Read reviews from past customers who have flown Avelo Airlines,JetBlue, andFrontier 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
7.6
Good

Comfort

7.1

Crew

8.3

Boarding

7.7

Food

5.1

Entertainment

5.0

Overall

7.6

Reviews

1 / 7
8.0
Excellent

Anonymous,Dec 2025

USA - ROC

The Customer Service department, particularly the baggage claim process, needs significant improvement. Currently, this department is only accessible via email, which makes resolving urgent issues difficult and frustrating. On December 8th, while traveling from Rochester, NY to Concord, NC, my elderly parent’s walker was never boarded onto the aircraft. This caused considerable frustration, stress, and disappointment during our travel. A mobility aid such as a walker is not optional—it is essential for my parent’s safety and independence. The failure to properly handle this item created a serious and avoidable issue. This situation significantly impacted our travel experience and highlights the need for better communication, accountability, and handling of mobility assistance devices. I hope this matter is taken seriously and that improvements are made to prevent similar incidents in the future.
Avelo Airlines
7.6
Good
Avelo Airlines
7.6
Good

Comfort

7.1

Crew

8.3

Boarding

7.7

Food

5.1

Entertainment

5.0

Overall

7.6

Reviews

1 / 7
8.0
Excellent

Anonymous,Dec 2025

USA - ROC

The Customer Service department, particularly the baggage claim process, needs significant improvement. Currently, this department is only accessible via email, which makes resolving urgent issues difficult and frustrating. On December 8th, while traveling from Rochester, NY to Concord, NC, my elderly parent’s walker was never boarded onto the aircraft. This caused considerable frustration, stress, and disappointment during our travel. A mobility aid such as a walker is not optional—it is essential for my parent’s safety and independence. The failure to properly handle this item created a serious and avoidable issue. This situation significantly impacted our travel experience and highlights the need for better communication, accountability, and handling of mobility assistance devices. I hope this matter is taken seriously and that improvements are made to prevent similar incidents in the future.
JetBlue
7.2
Good
2,985 reviews
Avelo Airlines
7.6
Good

Comfort

7.1

Crew

8.3

Boarding

7.7

Food

5.1

Entertainment

5.0

Overall

7.6

Reviews

1 / 7
8.0
Excellent

Anonymous,Dec 2025

USA - ROC

The Customer Service department, particularly the baggage claim process, needs significant improvement. Currently, this department is only accessible via email, which makes resolving urgent issues difficult and frustrating. On December 8th, while traveling from Rochester, NY to Concord, NC, my elderly parent’s walker was never boarded onto the aircraft. This caused considerable frustration, stress, and disappointment during our travel. A mobility aid such as a walker is not optional—it is essential for my parent’s safety and independence. The failure to properly handle this item created a serious and avoidable issue. This situation significantly impacted our travel experience and highlights the need for better communication, accountability, and handling of mobility assistance devices. I hope this matter is taken seriously and that improvements are made to prevent similar incidents in the future.
Frontier
5.6
Fair
2,929 reviews
Avelo Airlines
7.6
Good

Comfort

7.1

Crew

8.3

Boarding

7.7

Food

5.1

Entertainment

5.0

Overall

7.6

Reviews

1 / 7
8.0
Excellent

Anonymous,Dec 2025

USA - ROC

The Customer Service department, particularly the baggage claim process, needs significant improvement. Currently, this department is only accessible via email, which makes resolving urgent issues difficult and frustrating. On December 8th, while traveling from Rochester, NY to Concord, NC, my elderly parent’s walker was never boarded onto the aircraft. This caused considerable frustration, stress, and disappointment during our travel. A mobility aid such as a walker is not optional—it is essential for my parent’s safety and independence. The failure to properly handle this item created a serious and avoidable issue. This situation significantly impacted our travel experience and highlights the need for better communication, accountability, and handling of mobility assistance devices. I hope this matter is taken seriously and that improvements are made to prevent similar incidents in the future.

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.

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

    Looking at all options, your cheapest flight can be booked for $260. While the most popular route (Tweed-New Haven - San Juan Luis Munoz Marin Intl) can be booked for $228 on average, our data indicates $417 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, March is the cheapest month in which you can book a flight from New Haven to Puerto Rico (average of $78). Flying from New Haven to Puerto Rico in September is currently the most expensive (average of $260). 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

Browse thousands of different options on Cheapflights for your next trip

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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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John F Kennedy Intl to Santiago de los Caballeros flights
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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 May 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$89Average$309FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$158Average$325FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$208Average$364FlexibilityNo cancel feeOn-time62%

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