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$495+ Cheap flights from Redmond (RDM) 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — SJU
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheap flight deals from Redmond to Caribbean

Keep the following information in mind while searching for Redmond to Caribbean flight deals. Data was last updated October 28, 2025.

Round-trip from

$495
(United Airlines)
From Bend/Redmond to Caribbean
Search Deals

Find flight deals from Redmond to Caribbean

Cheapest flights from Redmond to Caribbean
Explore the most affordable flight options available from Redmond to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/25. 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.
Mon 12/88:00 amRDM - CUR
2 stops26h 44mAmerican Airlines
Thu 12/115:34 pmCUR - RDM
2 stops29h 59mAmerican Airlines
Deal found 10/25$795
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/32:57 pmRDM - STT
2 stops16h 44mAmerican Airlines
Fri 12/126:17 pmSTT - RDM
2 stops23h 16mAmerican Airlines
Deal found 10/28$804
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/102:58 pmRDM - MHH
2 stops22h 06mAmerican Airlines
Fri 11/1412:09 pmMHH - RDM
2 stops34h 16mAmerican Airlines
Deal found 10/26$1,077
This United deal was found by Cheapflights users on 10/27. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/87:51 pmRDM - STT
2 stops14h 39mMultiple Airlines
Sat 11/1510:21 amSTT - RDM
2 stops14h 46mMultiple Airlines
Deal found 10/27$1,089
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/123:49 pmRDM - STT
2 stops16h 11mUnited Airlines
Sun 11/163:35 pmSTT - RDM
2 stops24h 40mUnited Airlines
Deal found 10/28$1,135
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Mon 11/102:58 pmRDM - ANU
2 stops21h 48mAmerican Airlines
Thu 11/132:15 pmANU - RDM
2 stops28h 09mAmerican Airlines
Deal found 10/25$1,207
This United Airlines deal was found by Cheapflights users on 10/26. 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 10/271:54 pmRDM - POS
2 stops30h 29mUnited Airlines
Thu 10/3012:30 amPOS - RDM
2 stops15h 27mUnited Airlines
Deal found 10/26$1,213
This American Airlines deal was found by Cheapflights users on 10/26. 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 10/271:54 pmRDM - POS
2 stops21h 31mAmerican Airlines
Fri 10/317:00 amPOS - RDM
2 stops39h 32mAmerican Airlines
Deal found 10/26$1,249
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/87:51 pmRDM - STT
2 stops16h 27mUnited Airlines
Sat 11/153:35 pmSTT - RDM
2 stops24h 40mUnited Airlines
Deal found 10/28$1,295
This United deal was found by Cheapflights users on 10/27. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/211:17 pmRDM - STT
2 stops45h 13mMultiple Airlines
Mon 11/2412:01 pmSTT - RDM
2 stops13h 06mMultiple Airlines
Deal found 10/27$1,349
This United deal was found by Cheapflights users on 10/27. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/201:54 pmRDM - STT
2 stops19h 18mMultiple Airlines
Mon 11/2412:01 pmSTT - RDM
2 stops13h 06mMultiple Airlines
Deal found 10/27$1,368
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/216:00 amRDM - STT
3 stops52h 30mUnited Airlines
Mon 11/241:02 pmSTT - RDM
2 stops33h 13mUnited Airlines
Deal found 10/27$1,560

Cheapflights Fare Finder

 
Customize your flight search to find flights from Redmond 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 28, 2025.
Use the filters below to find and compare flights from Redmond to Caribbean that are best for you.

Fly from

Redmond

Fly to

Caribbean

Route

Depart

Return

Price

RedmondNassau

RDM - NAS

RDMNAS

Bend/Redmond

Fri 1/30

2:04 pm-1:33 pm

2 stops20h 29m

Nassau Intl

Sat 2/7

2:55 pm-9:21 pm

1 stop9h 26m

$495

RedmondNassau

RDM - NAS

RDMNAS

Bend/Redmond

Fri 1/30

5:20 pm-1:07 pm

2 stops16h 47m

Nassau Intl

Sat 2/7

1:41 pm-10:25 pm

2 stops11h 44m

$499

RedmondSanto Domingo

RDM - SDQ

RDMSDQ

Bend/Redmond

Mon 1/19

5:20 pm-7:14 pm

2 stops21h 54m

Santo Domingo Las Americas

Mon 1/26

8:45 pm-4:36 pm

2 stops23h 51m

$632

RedmondMontego Bay

RDM - MBJ

RDMMBJ

Bend/Redmond

Sun 3/1

12:35 pm-3:15 pm

2 stops23h 40m

Montego Bay Sangster Intl

Wed 3/4

8:00 am-11:39 pm

2 stops18h 39m

$700

RedmondMontego Bay

RDM - MBJ

RDMMBJ

Bend/Redmond

Wed 4/8

5:39 pm-11:55 am

2 stops16h 16m

Montego Bay Sangster Intl

Sat 4/18

11:35 am-11:32 pm

2 stops13h 57m

$789

RedmondWillemstad

RDM - CUR

RDMCUR

Bend/Redmond

Mon 12/8

8:00 am-2:44 pm

2 stops26h 44m

Willemstad Hato Int.

Thu 12/11

5:34 pm-7:33 pm

2 stops29h 59m

$795

RedmondSaint Thomas Island

RDM - STT

RDMSTT

Bend/Redmond

Wed 12/3

2:57 pm-3:42 pm

2 stops20h 45m

Saint Thomas Island Cyril E King

Fri 12/12

2:49 pm-1:33 pm

2 stops26h 44m

$804

RedmondSaint Thomas Island

RDM - STT

RDMSTT

Bend/Redmond

Tue 3/10

3:15 pm-12:55 pm

2 stops18h 40m

Saint Thomas Island Cyril E King

Wed 3/11

5:30 pm-12:47 pm

2 stops22h 17m

$859

RedmondNassau

RDM - NAS

RDMNAS

Bend/Redmond

Thu 4/16

5:45 pm-11:20 am

2 stops14h 35m

Nassau Intl

Fri 4/17

2:40 pm-12:09 am

2 stops12h 29m

$969

RedmondSaint Thomas Island

RDM - STT

RDMSTT

Bend/Redmond

Thu 1/8

6:53 pm-1:56 pm

2 stops15h 03m

Saint Thomas Island Cyril E King

Sun 1/18

1:02 pm-12:18 pm

2 stops27h 16m

$992

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 25 results
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2
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Best time to book a flight from Redmond to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Redmond 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 Redmond to Caribbean

What is the cheapest time of day to fly from RDM to CB?

Find hourly flight availability from Redmond to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 28, 2025.

When flying from Redmond to Caribbean, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 28% versus a flight in the evening.

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 28, 2025.
Read through reviews of airlines operating flights from Redmond to Caribbean, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,001 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,001 reviews
United Airlines
7.4
Good
9,001 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,032 reviews
United Airlines
7.4
Good
9,001 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

Related info for your journey

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

    Located just 1.8 mi from the city center, Bend/Redmond (RDM) is the airport most travelers will use when flying to Caribbean from Redmond.

  • How long is the flight from Redmond to Caribbean?

    There are many flights that can get you from Redmond to Caribbean in 16h 47m. Fly via United Airlines, Delta, or American Airlines to get the fastest option. Redmond and Caribbean are separated by a distance of 2770 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The most popular route from Redmond to Caribbean is Bend/Redmond - Saint Thomas Island Cyril E King. You may also consider Bend/Redmond - Santo Domingo Las Americas or Bend/Redmond - Willemstad Hato Int..

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Redmond 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 Redmond to Caribbean

Discover the top airline that operate flights from Redmond 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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$521Average$734FlexibilityNo cancel feeOn-time69%

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