Cheap flights To Roosevelt Roads (SJU) from $51

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Cheap Flights to Roosevelt Roads from $51 One Way, $85 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Jan 8 - Wed, Jan 21
SJU
Luis Munoz Marin Intl.
MAZ
Eugenio María de Hostos
$85 Roundtrip, found 6 days ago
$85
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Thu, Jan 8 from Luis Munoz Marin Intl. to Eugenio María de Hostos, returning Wed, Jan 21, priced at $85 found 6 days ago
Thu, Jan 1 - Thu, Jan 15
BOS
Logan Intl.
SJU
Luis Munoz Marin Intl.
$120 Roundtrip, found 6 hours ago
$120
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Thu, Jan 1 from Logan Intl. to Luis Munoz Marin Intl., returning Thu, Jan 15, priced at $120 found 6 hours ago
Mon, Feb 2 - Thu, Feb 12
BOS
Logan Intl.
SJU
Luis Munoz Marin Intl.
$136 Roundtrip, found 1 day ago
$136
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Feb 2 from Logan Intl. to Luis Munoz Marin Intl., returning Thu, Feb 12, priced at $136 found 1 day ago
Fri, Jan 23 - Thu, Jan 29
BOS
Logan Intl.
SJU
Luis Munoz Marin Intl.
$136 Roundtrip, just found
$136
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Jan 23 from Logan Intl. to Luis Munoz Marin Intl., returning Thu, Jan 29, priced at $136 just found
Thu, Mar 12 - Fri, Mar 13
SJU
Luis Munoz Marin Intl.
CPX
Benjamin Rivera Noriega
$138 Roundtrip, found 3 hours ago
$138
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Thu, Mar 12 from Luis Munoz Marin Intl. to Benjamin Rivera Noriega, returning Fri, Mar 13, priced at $138 found 3 hours ago
Sun, Feb 22 - Tue, Feb 24
SJU
Luis Munoz Marin Intl.
MAZ
Eugenio María de Hostos
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select Cape Air flight, departing Sun, Feb 22 from Luis Munoz Marin Intl. to Eugenio María de Hostos, returning Tue, Feb 24, priced at $138 found 1 day ago
Sun, May 3 - Wed, May 13
SJU
Luis Munoz Marin Intl.
VQS
Antonio Rivera Rodriguez
$158 Roundtrip, found 17 hours ago
$158
Roundtrip
found 17 hours ago
Select JetBlue Airways flight, departing Sun, May 3 from Luis Munoz Marin Intl. to Antonio Rivera Rodriguez, returning Wed, May 13, priced at $158 found 17 hours ago
Thu, Jan 8 - Thu, Jan 15
BOS
Logan Intl.
BQN
Rafael Hernandez
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Jan 8 from Logan Intl. to Rafael Hernandez, returning Thu, Jan 15, priced at $180 found 1 day ago
Thu, Jan 8 - Sat, Jan 17
BOS
Logan Intl.
PSE
Mercedita
$199 Roundtrip, found 2 days ago
$199
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Jan 8 from Logan Intl. to Mercedita, returning Sat, Jan 17, priced at $199 found 2 days ago
Tue, May 12 - Fri, May 15
BOS
Logan Intl.
SJU
Luis Munoz Marin Intl.
$202 Roundtrip, found 1 hour ago
$202
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, May 12 from Logan Intl. to Luis Munoz Marin Intl., returning Fri, May 15, priced at $202 found 1 hour ago

Roosevelt Roads Flight Information

Traveling To
Roosevelt Roads
Destination Airport IATA Code
SJU
Number of Airlines Serving
Airlines
Cape Air, Spirit Airlines, Frontier Airlines, JetBlue Airways, Delta
Flight Price
$85
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Roosevelt Roads economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Puerto Valdes
4.0-star property

Hotel Puerto Valdes

Feb 8 - Feb 13

5 night stay

Boston (BOS) to San Juan (SJU)

JetBlue Airways • Coach

San Juan (SJU) to Boston (BOS)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,052, price is now $539 per person
$539
per person
found 1 day ago
The Oliver Hotel
3.0-star property

The Oliver Hotel

Jan 27 - Feb 3

7 night stay

Boston (BOS) to San Juan (SJU)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $1,409, price is now $650 per person
$650
per person
found 1 day ago
Aire de O:live
4.0-star property

Aire de O:live

Jan 27 - Feb 3

7 night stay

Boston (BOS) to San Juan (SJU)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $2,715, price is now $1,435 per person
$1,435
per person
found 1 day ago
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See all available trips from Boston to Roosevelt Roads
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Roosevelt Roads premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Urbana Hotel
2.0-star property

Urbana Hotel

8.6/10 Excellent! (389 reviews)

Feb 15 - Feb 21

6 night stay

New York (JFK) to San Juan (SJU)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $1,666, price is now $1,137 per person
$1,137
per person
found 19 hours ago
For shopping you had to get in a car and take a drive. Available restaurants in walking distance.

Reviewed on Sep 26, 2025

Aire de O:live
4.0-star property

Aire de O:live

9/10 Wonderful! (328 reviews)

Feb 15 - Feb 21

6 night stay

New York (JFK) to San Juan (SJU)

JetBlue Airways • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,246, price is now $1,977 per person
$1,977
per person
found 19 hours ago
The staff were all fantastic. Very nice people. I wasn't crazy about the room. The windows are like an office building- they don't open. The Wifi was quite spotty. The sliding door for the toilet didnt work. The clothes closet didn't close properly. The bathroom sink was beautiful but the joystick spout was weird. Small complaints, really. But I would really have loved an open window...Great beach!

Reviewed on Apr 9, 2025

The Oliver Hotel
3.0-star property

The Oliver Hotel

9/10 Wonderful! (50 reviews)

Feb 15 - Feb 21

6 night stay

New York (JFK) to San Juan (SJU)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $1,813, price is now $1,169 per person
$1,169
per person
found 19 hours ago
Don't see what you're looking for?
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Roosevelt Roads business class flight packages

Price found within the past 48 hours. Click for updated prices.
Romeo Gay Hotel
4.0-star property

Romeo Gay Hotel

9/10 Wonderful! (121 reviews)

Feb 6 - Feb 14

8 night stay

Chicago (ORD) to San Juan (SJU)

American Airlines • Roundtrip • BusinessClass
Price was $2,104, price is now $1,425 per person
$1,425
per person
found 23 hours ago
OLV Fifty Five - Adults Only
4.5-star property

OLV Fifty Five - Adults Only

8.6/10 Excellent! (577 reviews)

Feb 6 - Feb 14

8 night stay

Chicago (ORD) to San Juan (SJU)

American Airlines • Roundtrip • BusinessClass
Save 100% on your flight
Price was $3,997, price is now $2,434 per person
$2,434
per person
found 23 hours ago
The hotel is overrated. The furniture in the rooms are filthy, and with so much condensation the floors are a fall hazard. Poor quality Wi-Fi and we’re charged $5 for utensils for our room service order. We could never reach the front desk even prior to check in to set up special in room services. The staff was very lackadaisical. This anniversary stay was very disappointing.

Reviewed on Aug 7, 2023

Aire de O:live
4.0-star property

Aire de O:live

9/10 Wonderful! (328 reviews)

Feb 16 - Feb 21

5 night stay

Chicago (ORD) to San Juan (SJU)

Delta • Non-stop • BusinessClass

San Juan (SJU) to Chicago (ORD)

American Airlines • Non-stop • BusinessClass
Price was $2,619, price is now $1,685 per person
$1,685
per person
found 1 day ago
The staff were all fantastic. Very nice people. I wasn't crazy about the room. The windows are like an office building- they don't open. The Wifi was quite spotty. The sliding door for the toilet didnt work. The clothes closet didn't close properly. The bathroom sink was beautiful but the joystick spout was weird. Small complaints, really. But I would really have loved an open window...Great beach!

Reviewed on Apr 9, 2025

Don't see what you're looking for?
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Roosevelt Roads first class flight packages

Price found within the past 48 hours. Click for updated prices.
Aire de O:live
4.0-star property

Aire de O:live

9/10 Wonderful! (328 reviews)

Feb 5 - Feb 9

4 night stay

Boston (BOS) to San Juan (SJU)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,384, price is now $1,626 per person
$1,626
per person
found 14 hours ago
The staff were all fantastic. Very nice people. I wasn't crazy about the room. The windows are like an office building- they don't open. The Wifi was quite spotty. The sliding door for the toilet didnt work. The clothes closet didn't close properly. The bathroom sink was beautiful but the joystick spout was weird. Small complaints, really. But I would really have loved an open window...Great beach!

Reviewed on Apr 9, 2025

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)
4.0-star property

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)

9/10 Wonderful! (645 reviews)

Feb 7 - Feb 14

7 night stay

New York (LGA) to San Juan (SJU)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $5,322, price is now $3,360 per person
$3,360
per person
found 1 day ago
Gorgeous, unique property. If you cannot stand the chain hotels and need a little character in your hotel, you will LOVE Olive. The rest is also amazing 5 star all the way.

Reviewed on Aug 9, 2025

The Oliver Hotel
3.0-star property

The Oliver Hotel

9/10 Wonderful! (50 reviews)

Feb 14 - Feb 22

8 night stay

Newark Liberty Intl. Airport (EWR) to San Juan (SJU)

United • Roundtrip • FirstClass
Price was $2,674, price is now $1,772 per person
$1,772
per person
found 1 day ago
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Roosevelt Roads

Why search for low cost fares on your flights to Roosevelt Roads when Orbitz offers the guaranteed lowest prices on foreign and domestic flights? When you travel with Orbitz you can benefit from:

Bargain Flights to Roosevelt Roads

Orbitz offers massive discounts and substantial last-minute savings on your Roosevelt Roads flights. Orbitz ensures that you can find, plan and reserve your flights any destination with ease, all while enjoying the guaranteed lowest prices available anywhere.

Cutting-Edge Mobile Tools to Keep You In The Know

Orbitz sends you free alerts and updates on your Roosevelt Roads flight wherever you are in the world. Once you have downloaded the free app for your iPhone, Android, or iPad, you can review or alter any travel plans that you have made or even book a future flight for business or pleasure. If you need to reserve a hotel room when booking your flight, you will find exclusive deals on our mobile site.

Frequent Flyer Program Enrolment

Orbitz finds you the lowest fares, but you can still add your miles to your frequent flyer program to earn miles or points on selected flights to Roosevelt Roads. When making your booking, reference your frequent flyer number to receive discounts in the future.

Outstanding Customer Service

Orbitz values your business and wants to ensure that all of your flights are as easy as possible to book. If you have booked a flight to Roosevelt Roads but need to cancel it, you may be able to do so online. If you have any questions or need help, the dedicated Orbitz customer service team is always standing by.

Frequently asked questions

How much is a flight to Roosevelt Roads?
Lots of fabulous deals were going begging this week, with return flights to Roosevelt Roads fluctuating from $85 to $202. But it was jet-setters flying in from San Juan (SJU) who nabbed the really big bargains. One-way flights to Roosevelt Roads started from a low $51.
How to book the cheapest flight to Roosevelt Roads?
Landing cheap flights to Roosevelt Roads is as simple as booking your ticket with Orbitz. But if you want to make sure you're getting the best flight deals around, here are some tips your wallet will love:

  • Consider departing from or arriving at alternative airports to increase your savings. Enter your preferred departure and arrival airports in the form fields, then choose the 'Nearby airports' function below. It will show you any available options.
  • If your plans aren't set in stone, click on the 'Show flexible dates' link to view the flight deals for a variety of departure dates. Go with any suitable cheaper fare you find.
  • You can also select the 'Show options' function to filter results for your preferred airline, seating class, nonstop flights and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you'd prefer to fly.
  • Reserve your fare as soon as you've worked out your travel dates. While you can get lucky once in a while, airfares rarely get more affordable as your departure date nears.
  • Combine your flights, hotels and car rentals into one convenient package deal. Save your hard-earned dollars for things you're really excited about, like exploring every corner of Roosevelt Roads.
  • Flying during the busy season often means costly airfares. Try to avoid traveling over popular dates, such as Easter, Thanksgiving and school breaks.

How long is a flight to Roosevelt Roads?
Flight lengths can vary for a number of reasons, including the location you set off from. If you're wondering whether you'll have time for a quick doze on your way to Roosevelt Roads, take a look at our list of common domestic routes and flight times:

  • Vieques (VQS-Antonio Rivera Rodriguez) to Luis Munoz Marin Intl. Airport (SJU) - 25 minutes
  • Mayaguez (MAZ-Eugenio Maria de Hostos) to Luis Munoz Marin Intl. Airport (SJU) - 37 minutes
  • Culebra (CPX-Benjamin Rivera Noriega) to Luis Munoz Marin Intl. Airport (SJU) - 35 minutes

What is the best time to book a flight to Roosevelt Roads?
On average, the cheapest time to reserve a plane ticket is January. This is followed by February then August. When searching for a cheap flight to Roosevelt Roads, make sure you're ready to book. Cheap deals pop up quickly and don't wait around!
What day of the week is the cheapest to book a flight to Roosevelt Roads?
You can get a great flight deal by booking on a Tuesday, Wednesday or Saturday. These are typically the best days to land cheap tickets to Roosevelt Roads.
What is the cheapest day of the week to fly to Roosevelt Roads?
You can pick up cheap flights to Roosevelt Roads by taking to the skies on a Monday, according to Orbitz data from 2020. Tuesday is also more affordable, while Saturday has the most costly ticket prices. Whether you prefer to save money or take off on whichever day is convenient, you'll always find a wonderful deal with Orbitz.
What is the cheapest month to fly to Roosevelt Roads?
We won't keep you in suspense — based on Orbitz data, August is generally the cheapest month to fly. Perfect for those who want to sneak in a weekend getaway or just an escape from it all before the weather changes. Be aware that the least affordable time to fly is in the middle of summer, with fares peaking in June.
Which airlines allow free cancellation?
We know that plans can change and flexibility is more important than ever. That's why you can easily search for flights that have free cancellation and no change fees on Orbitz. Just click on "Filter by flexible change policies" and we'll find you fares with more flexibility than a lip balm left in the sun!
What do I need for the flight to Roosevelt Roads?
Whether you're a seasoned flyer or it's your first time in the air, it helps to be organized when you travel. Here are some tips and things to bear in mind:

  • Make sure you've got your travel paperwork and identification. For international trips, you'll need your passport. When purchasing your seats, always use the exact details written on your government-issued ID.
  • A properly packed carry-on bag is the key to flying in comfort. Given your flight to Roosevelt Roads is no short hop, take enough snacks and things to keep you entertained. Something to read will help pass the time.
  • Air conditioning and high altitudes can create a cool environment. No matter what the season is in Roosevelt Roads, carry a sweater with you to keep nice and warm during your flight.

How many direct flights are there to Roosevelt Roads?
Your next exciting adventure is one easy plane ride away, with 251 direct flights to Roosevelt Roads every month. Search for your ideal flight with Orbitz and find a rewarding deal with JetBlue Airways, Cape Air or Spirit Airlines. Other reputable airlines that provide nonstop services include American Airlines, Frontier Airlines and Southwest Airlines.
How do I get cheap first-class/business deals to Roosevelt Roads?
There are ways of booking business or first-class tickets to Roosevelt Roads that won't burn through your wallet. Snap up a seat at the front of the plane for less with these useful tips:

  • Be more flexible with your travel dates and hold out for big sales on first or business-class airfares.
  • Many low-cost airlines offer quality business or premium-class seating that doesn't cost the earth.
  • Make the most of your airline's customer loyalty program and upgrade your seat. You can also bid for an upgrade in an online auction if available.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.