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Santiago de los Caballeros

$495+ Cheap flights from Portland, ME (PWM) to Santiago de los Caballeros (STI)

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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — STI
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Portland to Santiago de los Caballeros

Best flights from Portland to Santiago de los Caballeros
Discover carefully curated flight deals from Portland to Santiago de los Caballeros that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/9. 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 1/86:00 amPWM - STI
2 stops14h 46mAmerican Airlines
Sun 1/186:00 amSTI - PWM
2 stops17h 54mAmerican Airlines
Deal found 12/9$495
This United Airlines deal was found by Cheapflights users on 12/9. 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 2/23:12 pmPWM - STI
1 stop7h 39mUnited Airlines
Thu 2/56:00 amSTI - PWM
1 stop8h 56mUnited Airlines
Deal found 12/9$532
This Delta deal was found by Cheapflights users on 12/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/82:35 pmPWM - STI
1 stop9h 15mDelta
Sun 1/189:59 pmSTI - PWM
2 stops15h 04mDelta
Deal found 12/9$1,002
This United Airlines deal was found by Cheapflights users on 12/9. 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.
Thu 1/86:00 amPWM - STI
1 stop7h 53mUnited Airlines
Sun 1/186:00 amSTI - PWM
1 stop8h 56mUnited Airlines
Deal found 12/9$661

Find flight deals from Portland to Santiago de los Caballeros

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Santiago de los Caballeros (STI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 12, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$495
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$769
Provider with most accurate pricing for Boston Logan Intl-Santiago de los Caballeros flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Santiago de los Caballeros flights.
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From Portland to Santiago de los Caballeros
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Santiago de los Caballeros 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 12, 2025.
Use the filters below to find and compare flights from Portland to Santiago de los Caballeros that are best for you.

Fly from

Portland

Fly to

Santiago de los Caballeros

Route

Depart

Return

Price

PortlandSantiago de los Caballeros

PWM - STI

PWMSTI

Portland

Thu 1/8

6:00 am-9:46 pm

2 stops14h 46m

Santiago de los Caballeros

Sun 1/18

6:00 am-10:54 pm

2 stops17h 54m

$495

PortlandSantiago de los Caballeros

PWM - STI

PWMSTI

Portland

Mon 2/2

3:12 pm-11:51 pm

1 stop7h 39m

Santiago de los Caballeros

Thu 2/5

6:00 am-1:56 pm

1 stop8h 56m

$532

PortlandSantiago de los Caballeros

PWM - STI

PWMSTI

Portland

Thu 1/8

6:00 am-2:53 pm

1 stop7h 53m

Santiago de los Caballeros

Sun 1/18

6:00 am-1:56 pm

1 stop8h 56m

$661

PortlandSantiago de los Caballeros

PWM - STI

PWMSTI

Portland

Thu 1/8

2:35 pm-12:50 am

1 stop9h 15m

Santiago de los Caballeros

Sun 1/18

9:59 pm-12:03 pm

2 stops15h 04m

$1,002

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

Best time to book a flight from Portland to Santiago de los Caballeros

Have a flexible travel schedule? Discover the best time to fly to Santiago de los Caballeros from Portland 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 Portland to Santiago de los Caballeros

What is the cheapest month to book a flight from Portland, Maine to Santiago de los Caballeros?

Currently, November is the cheapest month in which you can book a flight from Portland, Maine to Santiago de los Caballeros (average of $227). Flying from Portland, Maine to Santiago de los Caballeros in July is currently the most expensive (average of $381). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Portland to Santiago de los Caballeros. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Portland, Maine to Santiago de los Caballeros?

    Airlines like American Airlines and United Airlines fly from Portland, Maine to Santiago de los Caballeros in about 7h 39m. The time it takes to get you to your destination can typically vary by up to 7h 07m. The distance from Portland, Maine to Santiago de los Caballeros is about 1674 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Portland to Santiago de los Caballeros that include hotel bookings?

    Yes. In addition to deals on Portland to Santiago de los Caballeros flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Santiago de los Caballeros?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Santiago de los Caballeros.

  • Can I find deals for business class flights from Portland to Santiago de los Caballeros?

    Yes. Cheapflights offers flight deals from Portland to Santiago de los Caballeros by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland, Maine to Santiago de los Caballeros?

    Currently, November is the cheapest month in which you can book a flight from Portland, Maine to Santiago de los Caballeros (average of $227). Flying from Portland, Maine to Santiago de los Caballeros in July is currently the most expensive (average of $381). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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