Search Cheap Flights to
Roosevelt Roads

Photo by Shannon Willitts

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Roosevelt Roads Flights as Low as $156

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

Frontier Airlines
Sat, May 24 - Sat, May 31
MCO
Orlando Intl.
SJU
Luis Munoz Marin Intl.
$156 Roundtrip, found 4 hours ago
$156
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, May 24 from Orlando Intl. to Luis Munoz Marin Intl., returning Sat, May 31, priced at $156 found 4 hours ago
Spirit Airlines
Sat, May 24 - Thu, May 29
MCO
Orlando Intl.
SJU
Luis Munoz Marin Intl.
$163 Roundtrip, found 6 days ago
$163
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Sat, May 24 from Orlando Intl. to Luis Munoz Marin Intl., returning Thu, May 29, priced at $163 found 6 days ago
Frontier Airlines
Sat, May 24 - Sat, May 31
MCO
Orlando Intl.
SJU
Luis Munoz Marin Intl.
$164 Roundtrip, found 4 hours ago
$164
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, May 24 from Orlando Intl. to Luis Munoz Marin Intl., returning Sat, May 31, priced at $164 found 4 hours ago
Spirit Airlines
Sat, May 24 - Sat, May 31
MCO
Orlando Intl.
SJU
Luis Munoz Marin Intl.
$169 Roundtrip, found 4 hours ago
$169
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sat, May 24 from Orlando Intl. to Luis Munoz Marin Intl., returning Sat, May 31, priced at $169 found 4 hours ago
Spirit Airlines
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SJU
Luis Munoz Marin Intl.
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Jun 15 from Orlando Intl. to Luis Munoz Marin Intl., returning Thu, Jun 19, priced at $170 found 1 day ago
Frontier Airlines
Wed, May 21 - Mon, Jun 2
MCO
Orlando Intl.
SJU
Luis Munoz Marin Intl.
$172 Roundtrip, found 23 hours ago
$172
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Wed, May 21 from Orlando Intl. to Luis Munoz Marin Intl., returning Mon, Jun 2, priced at $172 found 23 hours ago
Spirit Airlines
Fri, Aug 1 - Mon, Aug 11
BDL
Bradley Intl.
SJU
Luis Munoz Marin Intl.
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, Aug 1 from Bradley Intl. to Luis Munoz Marin Intl., returning Mon, Aug 11, priced at $187 found 1 day ago
Frontier Airlines
Mon, Jul 21 - Tue, Jul 29
MCO
Orlando Intl.
BQN
Rafael Hernandez
$200 Roundtrip, found 5 days ago
$200
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Jul 21 from Orlando Intl. to Rafael Hernandez, returning Tue, Jul 29, priced at $200 found 5 days ago
Frontier Airlines
Sun, Jul 13 - Wed, Jul 16
MCO
Orlando Intl.
PSE
Mercedita
$212 Roundtrip, found 2 days ago
$212
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Jul 13 from Orlando Intl. to Mercedita, returning Wed, Jul 16, priced at $212 found 2 days ago
JetBlue Airways
Wed, Jun 18 - Wed, Jun 25
MCO
Orlando Intl.
BQN
Rafael Hernandez
$237 Roundtrip, found 4 days ago
$237
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Jun 18 from Orlando Intl. to Rafael Hernandez, returning Wed, Jun 25, priced at $237 found 4 days ago
United
Sat, Sep 6 - Sat, Sep 13
BDL
Bradley Intl.
SJU
Luis Munoz Marin Intl.
$279 Roundtrip, found 5 days ago
$279
Roundtrip
found 5 days ago
Select United flight, departing Sat, Sep 6 from Bradley Intl. to Luis Munoz Marin Intl., returning Sat, Sep 13, priced at $279 found 5 days ago
Delta
Mon, May 12 - Fri, May 16
MCO
Orlando Intl.
SJU
Luis Munoz Marin Intl.
$309 Roundtrip, found 3 days ago
$309
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, May 12 from Orlando Intl. to Luis Munoz Marin Intl., returning Fri, May 16, priced at $309 found 3 days ago
American Airlines
Mon, May 12 - Fri, May 16
MCO
Orlando Intl.
SJU
Luis Munoz Marin Intl.
$309 Roundtrip, found 3 days ago
$309
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, May 12 from Orlando Intl. to Luis Munoz Marin Intl., returning Fri, May 16, priced at $309 found 3 days ago
Frontier Airlines
Sat, Aug 16 - Thu, Aug 21
BDL
Bradley Intl.
PSE
Mercedita
$328 Roundtrip, found 1 day ago
$328
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Aug 16 from Bradley Intl. to Mercedita, returning Thu, Aug 21, priced at $328 found 1 day ago
Frontier Airlines
Sat, May 24 - Thu, May 29
BDL
Bradley Intl.
BQN
Rafael Hernandez
$328 Roundtrip, found 1 day ago
$328
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 24 from Bradley Intl. to Rafael Hernandez, returning Thu, May 29, priced at $328 found 1 day ago
United
Sun, May 18 - Fri, Jun 6
BDL
Bradley Intl.
MAZ
Eugenio María de Hostos
$488 Roundtrip, found 4 days ago
$488
Roundtrip
found 4 days ago
Select United flight, departing Sun, May 18 from Bradley Intl. to Eugenio María de Hostos, returning Fri, Jun 6, priced at $488 found 4 days ago

Cheap Flights to Roosevelt Roads

Fall in love at first flight with your vacation to Roosevelt Roads by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Roosevelt Roads on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Roosevelt Roads, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Roosevelt Roads

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Roosevelt Roads with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the SJU airport.

What is the cheapest month to fly to Roosevelt Roads?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Roosevelt Roads are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Roosevelt Roads?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Roosevelt Roads.

What airport is best to fly into Roosevelt Roads?

When you’re planning your trip to Roosevelt Roads, convenience is the name of the game. Luckily, Roosevelt Roads Antonio Rivera Rodriguez Airport is nearby so you can deplane and get going on checking off everything on your Roosevelt Roads must-do list.

How much are flights to Roosevelt Roads?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Roosevelt Roads on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $156, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Roosevelt Roads?

The trick to saving a stack of cash on your flight to Roosevelt Roads? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $156 right now, why wait?

Last Minute Hotel Deals in Roosevelt Roads

El Conquistador Resort
El Conquistador Resort
4 out of 5
1000 Conquistador Avenue, Fajardo
The price is $408 per night from Jun 1 to Jun 2
$408
includes taxes & fees
Jun 1 - Jun 2
Stay at this 4-star beach hotel in Fajardo. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (2,828 reviews)
"It is a nice place, private beach. They have to work with the food in the island. No pizza at the island at all. Time that the food starts at the island is 11:00 AM. People join the boat by 9:00 AM arrival at the island by 9:20 AM have to wait until 11:00 AM to get something for eating."

Reviewed on May 7, 2025

El Conquistador Resort
Hyatt Regency Grand Reserve Puerto Rico
Hyatt Regency Grand Reserve Puerto Rico
4 out of 5
200 Coco Beach Blvd. Highway 955-I, Río Grande
The price is $359 per night from May 12 to May 13
$359
includes taxes & fees
May 12 - May 13
Stay at this 4-star beach resort in Río Grande. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the breakfast and the pool in our ...
8.8/10 Excellent! (2,108 reviews)
"I had the privilege of staying beachfront, and it was truly breathtaking. I walked 20 feet from my sliding door and found myself on the sand. Witnessing the sunrise and sunset from the comfort of my patio daybed was a daily highlight. The staff were exceptional, providing top-notch customer service. ..."

Reviewed on May 6, 2025

Hyatt Regency Grand Reserve Puerto Rico
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
5 out of 5
6000 Rio Mar Boulevard, Río Grande
The price is $391 per night from May 29 to May 30
$391
includes taxes & fees
May 29 - May 30
Stay at this 5-star luxury resort in Río Grande. Enjoy 4 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the pool and the helpful staff ...
8.4/10 Very Good! (2,039 reviews)
"Muy"

Reviewed on May 5, 2025

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
Wyndham Palmas Beach and Golf Boutique Resort
Wyndham Palmas Beach and Golf Boutique Resort
4 out of 5
170 Candelero Drive, Palmas del Mar, Humacao
The price is $225 per night from May 18 to May 19
$225
includes taxes & fees
May 18 - May 19
Stay at this 4-star beach resort in Humacao. Enjoy free WiFi, 2 outdoor pools, and 5 restaurants. Our guests praise the pool and the helpful staff in our reviews. ...
8.2/10 Very Good! (517 reviews)
"I enjoyed this place, the staff, the food. For this location you need transportation, we had to uber everywhere and that was the downside. Other than that great place to relax, walk to the beach"

Reviewed on Apr 27, 2025

Wyndham Palmas Beach and Golf Boutique Resort
Fairfield by Marriott Luquillo Beach
Fairfield by Marriott Luquillo Beach
3.5 out of 5
3KM 36.0 MATA DE PLATANO, Luquillo
The price is $204 per night from May 11 to May 12
$204
includes taxes & fees
May 11 - May 12
Stay at this 3.5-star beach hotel in Luquillo. Enjoy free breakfast, free WiFi, and a casino. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.2/10 Wonderful! (571 reviews)
"Great choice for families"

Reviewed on Apr 30, 2025

Fairfield by Marriott Luquillo Beach
Sea Gate Hotel
Sea Gate Hotel
2.5 out of 5
Route 989 Km .04, Vieques
The price is $105 per night from May 10 to May 11
$105
includes taxes & fees
May 10 - May 11
Book a stay at this family-friendly hotel in Vieques. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,003 reviews)
Best little island hotel
"Amazing little hotel great owners beautiful view from the room. Very helpful with all question would definitely stay again!"

Reviewed on May 6, 2025

Sea Gate Hotel
The St. Regis Bahia Beach Resort, Puerto Rico
The St. Regis Bahia Beach Resort, Puerto Rico
5 out of 5
State Road 187 Kilometer 4.2, Río Grande
The price is $1,046 per night from Jun 8 to Jun 9
$1,046
includes taxes & fees
Jun 8 - Jun 9
Stay at this 5-star luxury resort in Río Grande. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (424 reviews)
"The property was wonderful, clean, quiet and beautiful. Our only complaint was a lack of restaurant options on property."

Reviewed on Apr 9, 2025

The St. Regis Bahia Beach Resort, Puerto Rico
Fajardo Inn
Fajardo Inn
4 out of 5
52 Parcelas Beltran, Puerto Real, Fajardo
The price is $185 per night from May 11 to May 12
$185
includes taxes & fees
May 11 - May 12
Stay at this 4-star hotel in Fajardo. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions El Conquistador Golf Course and Bahía Las Croabas ...
7.8/10 Good! (999 reviews)
"The facilities are well maintained. Everything was clean."

Reviewed on Apr 29, 2025

Fajardo Inn
See all 2,039 properties in Roosevelt Roads
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.