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Santiago de los Caballeros

$469+ Cheap flights from Chesapeake, VA 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — STI
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
1 adult, Economy
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Cheap flight deals from Chesapeake to Santiago de los Caballeros

Keep the following information in mind while searching for Chesapeake to Santiago de los Caballeros flight deals. Data was last updated julio 31, 2025.

Round-trip from

$421
(American Airlines)

Popular in

April

Cheapest in

June

Average price

$579
From Chesapeake to Santiago de los Caballeros
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Chesapeake to Santiago de los Caballeros

Cheapest flights from Chesapeake to Santiago de los Caballeros
Explore the most affordable flight options available from Chesapeake to Santiago de los Caballeros. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 31, 2025.

This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/195:30 amORF - STI
1 stop27h 45mSpirit Airlines
lun. 8/2510:20 amSTI - ORF
1 stop12h 14mSpirit Airlines
Deal found 7/30$469
This American Airlines deal was found by Cheapflights users on 7/30. 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.
vie. 9/266:15 amORF - STI
1 stop6h 12mAmerican Airlines
lun. 9/291:29 pmSTI - ORF
1 stop10h 30mAmerican Airlines
Deal found 7/30$475
This Delta deal was found by Cheapflights users on 7/31. 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.
jue. 8/75:28 pmORF - STI
1 stop7h 19mDelta
lun. 8/118:55 pmSTI - ORF
1 stop14h 47mDelta
Deal found 7/31$633
This JetBlue deal was found by Cheapflights users on 7/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/195:57 pmORF - STI
1 stop7h 41mJetBlue
dom. 8/243:08 amSTI - ORF
1 stop13h 54mJetBlue
Deal found 7/30$791
This Mytrip deal was found by Cheapflights users on 7/30. 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.
vie. 8/110:20 amORF - STI
2 stops23h 30mMultiple Airlines
vie. 8/810:55 amSTI - ORF
3 stops22h 28mMultiple Airlines
Deal found 7/30$960
This United Airlines deal was found by Cheapflights users on 7/31. 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.
jue. 8/76:10 amORF - STI
2 stops9h 02mUnited Airlines
lun. 8/116:00 amSTI - ORF
3 stops33h 14mUnited Airlines
Deal found 7/31$966

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake 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 julio 31, 2025.
Use the filters below to find and compare flights from Chesapeake to Santiago de los Caballeros that are best for you.

Fly from

Chesapeake

Fly to

Santiago de los Caballeros

Route

Depart

Return

Price

NorfolkSantiago de los Caballeros

ORF - STI

ORFSTI

Norfolk

mar. 8/19

5:30 am-9:15 am

1 stop27h 45m

Santiago de los Caballeros

lun. 8/25

10:20 am-10:34 pm

1 stop12h 14m

$469

NorfolkSantiago de los Caballeros

ORF - STI

ORFSTI

Norfolk

vie. 9/26

6:15 am-12:27 pm

1 stop6h 12m

Santiago de los Caballeros

lun. 9/29

1:29 pm-11:59 pm

1 stop10h 30m

$475

NorfolkSantiago de los Caballeros

ORF - STI

ORFSTI

Norfolk

mar. 8/19

5:57 pm-1:38 am

1 stop7h 41m

Santiago de los Caballeros

dom. 8/24

3:08 am-5:02 pm

1 stop13h 54m

$791

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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

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

What is the cheapest month to book a flight from Chesapeake to Santiago de los Caballeros?

Currently, May is the cheapest month in which you can book a flight from Chesapeake to Santiago de los Caballeros (average of $347). Flying from Chesapeake to Santiago de los Caballeros in July is currently the most expensive (average of $603). 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.

Reviews of airlines servicing Santiago de los Caballeros

Get insights into the airlines that provide service to Santiago de los Caballeros. 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 Santiago de los Caballeros. Reviews last updated julio 31, 2025.
See what other customers who have flown with JetBlue, American Airlines, and Spirit Airlines from Chesapeake to Santiago de los Caballeros have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.3
Good
2,914 reviews

Crew

8.0

Food

6.7

Boarding

7.4

Comfort

7.6

Entertainment

7.3

Overall

7.3

Reviews

1 / 20
2.0
Mediocre

Kevin,Jul 2025

JFK - POS

Flight was delayed a couple hours with no explanation. The aircraft was changed and so did our seating arrangement with no notice.
JetBlue
7.3
Good
2,914 reviews
JetBlue
7.3
Good
2,914 reviews

Crew

8.0

Food

6.7

Boarding

7.4

Comfort

7.6

Entertainment

7.3

Overall

7.3

Reviews

1 / 20
2.0
Mediocre

Kevin,Jul 2025

JFK - POS

Flight was delayed a couple hours with no explanation. The aircraft was changed and so did our seating arrangement with no notice.
American Airlines
7.2
Good
10,000 reviews
JetBlue
7.3
Good
2,914 reviews

Crew

8.0

Food

6.7

Boarding

7.4

Comfort

7.6

Entertainment

7.3

Overall

7.3

Reviews

1 / 20
2.0
Mediocre

Kevin,Jul 2025

JFK - POS

Flight was delayed a couple hours with no explanation. The aircraft was changed and so did our seating arrangement with no notice.
Spirit Airlines
6.3
Okay
8,049 reviews
JetBlue
7.3
Good
2,914 reviews

Crew

8.0

Food

6.7

Boarding

7.4

Comfort

7.6

Entertainment

7.3

Overall

7.3

Reviews

1 / 20
2.0
Mediocre

Kevin,Jul 2025

JFK - POS

Flight was delayed a couple hours with no explanation. The aircraft was changed and so did our seating arrangement with no notice.

Related info for your journey

Find useful and relevant information for your journey from Chesapeake 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.

  • What airport do you fly into for flights to Santiago de los Caballeros from Chesapeake?

    Located just 6.8 mi from the city center, Santiago de los Caballeros is the airport most travelers will use when flying to Santiago de los Caballeros from Chesapeake. Booking flights from Chesapeake to Santiago (STI) should be relatively easy as there are 0 daily inbound flights from Chesapeake from 4 different airlines.

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

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

  • How can I find direct flights from Chesapeake 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 Chesapeake to Santiago de los Caballeros.

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

    Yes. Cheapflights offers flight deals from Chesapeake 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 Chesapeake to Santiago de los Caballeros?

    Currently, May is the cheapest month in which you can book a flight from Chesapeake to Santiago de los Caballeros (average of $347). Flying from Chesapeake to Santiago de los Caballeros in July is currently the most expensive (average of $603). 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.

See more FAQs

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Alternative routes for Chesapeake to Santiago de los Caballeros

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Chesapeake to Santiago de los Caballeros

Discover the top 4 airlines that operate flights from Chesapeake to Santiago de los Caballeros. 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$268Average$526FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$346Average$640FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$426Average$658FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$434Average$629FlexibilityNo cancel feeOn-time71%

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