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Caribbean

$495+ 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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
BIL — SJU
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
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Find flight deals from Billings to Caribbean

Cheapest flights from Billings to Caribbean
Explore the most affordable flight options available from Billings to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2025.

This American Airlines deal was found by Cheapflights users on 10/20. 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 12/41:58 pmBIL - SJU
2 stops17h 11mAmerican Airlines
Mon 12/86:42 pmSJU - BIL
2 stops21h 46mAmerican Airlines
Deal found 10/20$570
This Mytrip deal was found by Cheapflights users on 10/19. 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.
Fri 11/215:21 pmBIL - SJU
3 stops28h 03mMultiple Airlines
Thu 11/2711:55 amSJU - BIL
2 stops27h 10mMultiple Airlines
Deal found 10/19$612
This American Airlines deal was found by Cheapflights users on 10/20. 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 12/61:58 pmBIL - SJU
2 stops20h 32mAmerican Airlines
Mon 12/157:00 amSJU - BIL
1 stop17h 18mAmerican Airlines
Deal found 10/20$618
This United Airlines deal was found by Cheapflights users on 10/18. 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 12/87:00 amBIL - SJU
1 stop8h 25mUnited Airlines
Thu 12/118:30 amSJU - BIL
2 stops15h 51mUnited Airlines
Deal found 10/18$621
This American Airlines deal was found by Cheapflights users on 10/18. 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 12/85:10 amBIL - SJU
2 stops15h 43mAmerican Airlines
Thu 12/116:42 pmSJU - BIL
2 stops21h 46mAmerican Airlines
Deal found 10/18$641
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Wed 11/57:00 amBIL - PUJ
1 stop8h 18mUnited Airlines
Thu 11/132:05 pmPUJ - BIL
1 stop10h 13mUnited Airlines
Deal found 10/19$763
This American Airlines deal was found by Cheapflights users on 10/19. 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 12/41:58 pmBIL - AUA
2 stops21h 44mAmerican Airlines
Wed 12/105:59 pmAUA - BIL
2 stops22h 29mAmerican Airlines
Deal found 10/19$794
This United Airlines deal was found by Cheapflights users on 10/17. 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 12/82:40 pmBIL - AUA
2 stops20h 00mUnited Airlines
Thu 12/112:50 pmAUA - BIL
2 stops25h 28mUnited Airlines
Deal found 10/17$800
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Wed 12/177:00 amBIL - PUJ
1 stop8h 18mUnited Airlines
Tue 12/2312:56 pmPUJ - BIL
2 stops35h 28mUnited Airlines
Deal found 10/19$838
This American Airlines deal was found by Cheapflights users on 10/19. 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 11/162:00 pmBIL - STX
2 stops22h 12mAmerican Airlines
Fri 11/216:42 pmSTX - BIL
2 stops21h 48mAmerican Airlines
Deal found 10/19$839
This American Airlines deal was found by Cheapflights users on 10/19. 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 12/171:58 pmBIL - PUJ
2 stops23h 06mAmerican Airlines
Tue 12/235:23 pmPUJ - BIL
2 stops23h 01mAmerican Airlines
Deal found 10/19$865

Cheap flight deals from Billings to Caribbean

Keep the following information in mind while searching for Billings to Caribbean flight deals. Data was last updated October 20, 2025.

Round-trip from

$495
(United Airlines)

Popular in

December

Cheapest in

January

Average price

$700
From Billings Logan Intl to Caribbean
Search Deals
High demand for flights, 3% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 20, 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

Wed 3/18

7:00 am-9:22 pm

2 stops12h 22m

San Juan Luis Munoz Marin Intl

Thu 3/26

1:25 pm-8:54 pm

1 stop9h 29m

$495

BillingsSan Juan

BIL - SJU

BILSJU

Billings Logan Intl

Sat 2/7

2:15 pm-12:32 pm

2 stops19h 17m

San Juan Luis Munoz Marin Intl

Sat 2/14

8:04 am-8:57 pm

1 stop15h 53m

$570

BillingsSan Juan

BIL - SJU

BILSJU

Billings Logan Intl

Thu 12/4

1:58 pm-10:09 am

2 stops17h 11m

San Juan Luis Munoz Marin Intl

Mon 12/8

6:42 pm-1:28 pm

2 stops21h 46m

$570

BillingsSan Juan

BIL - SJU

BILSJU

Billings Logan Intl

Sat 12/6

1:58 pm-1:30 pm

2 stops20h 32m

San Juan Luis Munoz Marin Intl

Mon 12/15

6:42 pm-1:28 pm

2 stops21h 46m

$618

BillingsSan Juan

BIL - SJU

BILSJU

Billings Logan Intl

Tue 3/31

2:03 pm-3:55 am

1 stop11h 52m

San Juan Luis Munoz Marin Intl

Tue 4/7

6:59 am-8:46 pm

1 stop15h 47m

$618

BillingsSan Juan

BIL - SJU

BILSJU

Billings Logan Intl

Mon 12/8

7:00 am-6:25 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Thu 12/11

8:30 am-9:21 pm

2 stops15h 51m

$621

BillingsSan Juan

BIL - SJU

BILSJU

Billings Logan Intl

Sat 2/7

4:13 pm-6:11 am

2 stops10h 58m

San Juan Luis Munoz Marin Intl

Sat 2/14

8:35 am-9:21 pm

2 stops15h 46m

$621

BillingsPunta Cana

BIL - PUJ

BILPUJ

Billings Logan Intl

Tue 1/6

2:45 pm-12:59 pm

2 stops19h 14m

Punta Cana

Thu 1/15

2:05 pm-9:23 pm

1 stop10h 18m

$628

BillingsPunta Cana

BIL - PUJ

BILPUJ

Billings Logan Intl

Tue 1/6

5:59 pm-4:21 pm

2 stops19h 22m

Punta Cana

Thu 1/15

4:50 pm-11:08 am

2 stops21h 18m

$632

BillingsSanto Domingo

BIL - SDQ

BILSDQ

Billings Logan Intl

Tue 3/10

5:40 am-11:42 pm

2 stops16h 02m

Santo Domingo Las Americas

Thu 3/12

7:05 am-10:37 pm

2 stops17h 32m

$672

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/18

Showing 1-10 of 22 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 October 20, 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
8,991 reviews

Crew

8.1

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,991 reviews
United Airlines
7.4
Good
8,991 reviews

Crew

8.1

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

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?

    United Airlines, American Airlines, and Delta can get you from Billings to Caribbean in just under 12h 22m. Your travel time can differ by up to 7h. The distance from Billings to Caribbean is about 3068 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 - Punta Cana or Billings Logan Intl - Santo Domingo Las Americas 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 October 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$495Average$804FlexibilityNo cancel feeOn-time69%

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