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$531+ Cheap flights from Billings (BIL) to Caribbean

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
BIL — SJU
Jan 26 — Feb 21
Mon 1/26
Mon 2/2
1 adult, Economy
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Cheap flight deals from Billings to Caribbean

Best flights from Billings to Caribbean
Discover carefully curated flight deals from Billings to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 27, 2025.

This American Airlines deal was found by Cheapflights users on 12/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/72:15 pmBIL - SJU
2 stops17h 33mAmerican Airlines
Sat 2/147:30 amSJU - BIL
1 stop17h 05mAmerican Airlines
Deal found 12/25$531
This United Airlines deal was found by Cheapflights users on 12/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/285:05 amBIL - SJU
2 stops13h 29mUnited Airlines
Sat 5/91:00 amSJU - BIL
2 stops14h 13mUnited Airlines
Deal found 12/24$603
This Air Canada deal was found by Cheapflights users on 12/25. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/282:35 pmBIL - AUA
2 stops22h 35mAir Canada
Thu 4/304:05 pmAUA - BIL
2 stops43h 46mAir Canada
Deal found 12/25$695
This American Airlines deal was found by Cheapflights users on 12/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/297:50 amBIL - SJU
1 stop18h 10mAmerican Airlines
Sat 5/911:59 pmSJU - BIL
1 stop13h 56mAmerican Airlines
Deal found 12/26$570
This American Airlines deal was found by Cheapflights users on 12/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:50 amBIL - SJU
1 stop18h 10mAmerican Airlines
Sun 5/1011:59 pmSJU - BIL
1 stop13h 56mAmerican Airlines
Deal found 12/24$570
This United Airlines deal was found by Cheapflights users on 12/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/255:51 pmBIL - PUJ
2 stops16h 49mUnited Airlines
Mon 6/13:35 pmPUJ - BIL
2 stops20h 16mUnited Airlines
Deal found 12/25$632
This American Airlines deal was found by Cheapflights users on 12/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/181:51 pmBIL - SJU
2 stops17h 09mAmerican Airlines
Tue 3/246:33 amSJU - BIL
1 stop17h 17mAmerican Airlines
Deal found 12/24$570
This Travelocity deal was found by Cheapflights users on 12/25. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/142:35 pmBIL - AUA
2 stops21h 25mAir Canada
Tue 2/174:05 pmAUA - BIL
2 stops32h 17mAir Canada
Deal found 12/25$698
This United Airlines deal was found by Cheapflights users on 12/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/304:15 pmBIL - PUJ
2 stops18h 00mUnited Airlines
Sat 6/64:00 pmPUJ - BIL
2 stops19h 51mUnited Airlines
Deal found 12/25$682
This Air Canada deal was found by Cheapflights users on 12/24. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/252:45 pmBIL - AUA
2 stops21h 15mAir Canada
Thu 1/294:05 pmAUA - BIL
2 stops26h 17mAir Canada
Deal found 12/24$710
This United Airlines deal was found by Cheapflights users on 12/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/282:35 pmBIL - SDQ
2 stops20h 06mUnited Airlines
Wed 3/42:53 pmSDQ - BIL
2 stops22h 00mUnited Airlines
Deal found 12/25$742
This United Airlines deal was found by Cheapflights users on 12/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:00 amBIL - PUJ
1 stop8h 18mUnited Airlines
Wed 3/42:05 pmPUJ - BIL
1 stop10h 17mUnited Airlines
Deal found 12/24$766
This American Airlines deal was found by Cheapflights users on 12/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/82:15 pmBIL - SDQ
2 stops24h 14mAmerican Airlines
Sat 2/217:00 amSDQ - BIL
2 stops19h 01mAmerican Airlines
Deal found 12/25$782
This Air Canada deal was found by Cheapflights users on 12/24. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:00 amBIL - PUJ
2 stops35h 35mAir Canada
Wed 3/410:35 pmPUJ - BIL
2 stops25h 32mAir Canada
Deal found 12/24$885
This United Airlines deal was found by Cheapflights users on 12/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/96:30 amBIL - PUJ
1 stop8h 48mUnited Airlines
Mon 2/1612:56 pmPUJ - BIL
2 stops23h 54mUnited Airlines
Deal found 12/26$767
This American Airlines deal was found by Cheapflights users on 12/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/261:51 pmBIL - AUA
2 stops24h 14mAmerican Airlines
Wed 4/15:13 pmAUA - BIL
2 stops22h 08mAmerican Airlines
Deal found 12/26$794
This United Airlines deal was found by Cheapflights users on 12/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/252:45 pmBIL - SDQ
2 stops19h 56mUnited Airlines
Thu 1/292:53 pmSDQ - BIL
2 stops21h 57mUnited Airlines
Deal found 12/24$782
This American Airlines deal was found by Cheapflights users on 12/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3012:23 pmBIL - PUJ
1 stop23h 17mAmerican Airlines
Sat 6/612:00 pmPUJ - BIL
2 stops12h 41mAmerican Airlines
Deal found 12/25$810
This American Airlines deal was found by Cheapflights users on 12/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/92:15 pmBIL - UVF
2 stops21h 48mAmerican Airlines
Mon 2/163:50 pmUVF - BIL
2 stops24h 33mAmerican Airlines
Deal found 12/26$837
This American Airlines deal was found by Cheapflights users on 12/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/251:51 pmBIL - AUA
2 stops24h 14mAmerican Airlines
Thu 4/25:13 pmAUA - BIL
2 stops22h 08mAmerican Airlines
Deal found 12/26$878
This American Airlines deal was found by Cheapflights users on 12/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/12:15 pmBIL - UVF
2 stops20h 31mAmerican Airlines
Sat 2/75:02 pmUVF - BIL
2 stops23h 34mAmerican Airlines
Deal found 12/26$887
This United Airlines deal was found by Cheapflights users on 12/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/2610:52 amBIL - KIN
2 stops25h 01mUnited Airlines
Thu 1/293:00 pmKIN - BIL
2 stops32h 23mUnited Airlines
Deal found 12/24$1,318
This United Airlines deal was found by Cheapflights users on 12/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/142:35 pmBIL - AUA
2 stops20h 15mUnited Airlines
Tue 2/175:50 pmAUA - BIL
3 stops30h 32mUnited Airlines
Deal found 12/25$5,576

Find flight deals from Billings to Caribbean

Keep the following information in mind while searching for Billings to Caribbean flight deals. Data was last updated December 27, 2025.

Round-trip from

$531
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$915
From Billings Logan Intl to Caribbean
Search Deals
High demand for flights, 4% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Billings to Caribbean 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 December 27, 2025.
Use the filters below to find and compare flights from Billings to Caribbean that are best for you.

Fly from

Billings

Fly to

Caribbean

Route

Depart

Return

Price

BillingsSan Juan

BIL - SJU

BILSJU

Billings Logan Intl

Sat 2/7

2:15 pm-10:48 am

2 stops17h 33m

San Juan Luis Munoz Marin Intl

Sat 2/14

7:30 am-9:35 pm

1 stop17h 05m

$531

BillingsSan Juan

BIL - SJU

BILSJU

Billings Logan Intl

Wed 4/29

7:50 am-4:00 am

1 stop18h 10m

San Juan Luis Munoz Marin Intl

Sat 5/9

11:59 pm-11:55 am

1 stop13h 56m

$570

BillingsSan Juan

BIL - SJU

BILSJU

Billings Logan Intl

Tue 4/28

7:50 am-4:00 am

1 stop18h 10m

San Juan Luis Munoz Marin Intl

Sun 5/10

11:59 pm-11:55 am

1 stop13h 56m

$570

BillingsSan Juan

BIL - SJU

BILSJU

Billings Logan Intl

Wed 3/18

1:51 pm-9:00 am

2 stops17h 09m

San Juan Luis Munoz Marin Intl

Tue 3/24

6:33 am-9:50 pm

1 stop17h 17m

$570

BillingsSan Juan

BIL - SJU

BILSJU

Billings Logan Intl

Tue 4/28

5:05 am-8:34 pm

2 stops13h 29m

San Juan Luis Munoz Marin Intl

Sat 5/9

1:00 am-1:13 pm

2 stops14h 13m

$603

BillingsPunta Cana

BIL - PUJ

BILPUJ

Billings Logan Intl

Mon 5/25

5:51 pm-12:40 pm

2 stops16h 49m

Punta Cana

Mon 6/1

3:35 pm-9:51 am

2 stops20h 16m

$632

BillingsPunta Cana

BIL - PUJ

BILPUJ

Billings Logan Intl

Sat 5/30

4:15 pm-12:15 pm

2 stops18h 00m

Punta Cana

Sat 6/6

4:00 pm-9:51 am

2 stops19h 51m

$682

BillingsOranjestad

BIL - AUA

BILAUA

Billings Logan Intl

Tue 4/28

2:35 pm-3:10 pm

2 stops22h 35m

Oranjestad Reina Beatrix

Thu 4/30

4:05 pm-9:51 am

2 stops43h 46m

$695

BillingsOranjestad

BIL - AUA

BILAUA

Billings Logan Intl

Sat 2/14

2:35 pm-3:00 pm

2 stops21h 25m

Oranjestad Reina Beatrix

Tue 2/17

4:05 pm-9:22 pm

2 stops32h 17m

$698

BillingsOranjestad

BIL - AUA

BILAUA

Billings Logan Intl

Sun 1/25

2:45 pm-3:00 pm

2 stops21h 15m

Oranjestad Reina Beatrix

Thu 1/29

4:05 pm-3:22 pm

2 stops26h 17m

$710

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Showing 1-10 of 23 results
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Best time to book a flight from Billings to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Billings 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 Billings to Caribbean
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated December 27, 2025.
See what other customers who have flown with United Airlines from Billings to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,116 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,116 reviews
United Airlines
7.4
Good
9,116 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

Related info for your journey

Find useful and relevant information for your journey from Billings to Caribbean. 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 Billings to Caribbean?

    Billings Logan Intl (BIL), located 2.7 mi from the city center, is the airport you fly out of when you book flights from Billings to Caribbean.

  • How long is the flight from Billings to Caribbean?

    American Airlines, United Airlines, and Air Canada can get you from Billings to Caribbean in just under 16h 49m. Your travel time can differ by up to 5h 46m. The distance from Billings to Caribbean is about 2958 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Billings to Caribbean?

    Most travelers choose Billings Logan Intl - San Juan Luis Munoz Marin Intl, Billings Logan Intl - Santo Domingo Las Americas or Billings Logan Intl - Punta Cana when deciding on the best route from Billings to Caribbean.

  • Can I find deals for flights from Billings to Caribbean that include hotel bookings?

    Yes. In addition to deals on Billings to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Billings to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Billings to Caribbean.

  • Can I find deals for business class flights from Billings to Caribbean?

    Yes. Cheapflights offers flight deals from Billings to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Top airline flying from Billings to Caribbean

Discover the top airline that operate flights from Billings to Caribbean. 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 December 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$495Average$655FlexibilityNo cancel feeOn-time69%

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