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Santiago de los Caballeros

$368+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — STI
nov 28 — dez 51
sex 11/28
sex 12/5
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 outubro 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$378
(CheapOair)

Popular in

April

Cheapest in

June

Average price

$526
Provider with most accurate pricing for Norfolk-Santiago de los Caballeros flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Santiago de los Caballeros flights.
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From Chesapeake to Santiago de los Caballeros
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($75 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in October 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 outubro 29, 2025.

This CheapOair deal was found by Cheapflights users on 10/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 12/148:11 pmORF - STI
1 stop5h 31mSpirit Airlines
dom 12/213:43 amSTI - ORF
1 stop11h 23mSpirit Airlines
Deal found 10/29$368
This American Airlines deal was found by Cheapflights users on 10/29. 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.
seg 12/85:00 amORF - STI
1 stop9h 32mAmerican Airlines
ter 12/164:32 pmSTI - ORF
1 stop8h 27mAmerican Airlines
Deal found 10/29$468
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.
dom 12/145:00 amORF - STI
1 stop14h 33mAmerican Airlines
seg 12/226:17 pmSTI - ORF
1 stop7h 42mAmerican Airlines
Deal found 10/28$553

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 outubro 29, 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

dom 12/14

8:11 pm-2:42 am

1 stop5h 31m

Santiago de los Caballeros

dom 12/21

3:43 am-2:06 pm

1 stop11h 23m

$368

NorfolkSantiago de los Caballeros

ORF - STI

ORFSTI

Norfolk

seg 12/8

5:00 am-3:32 pm

1 stop9h 32m

Santiago de los Caballeros

ter 12/16

6:00 am-6:59 pm

1 stop13h 59m

$468

NorfolkSantiago de los Caballeros

ORF - STI

ORFSTI

Norfolk

qui 3/26

12:15 pm-11:27 pm

1 stop11h 12m

Santiago de los Caballeros

ter 4/7

6:00 am-4:49 pm

1 stop10h 49m

$478

NorfolkSantiago de los Caballeros

ORF - STI

ORFSTI

Norfolk

seg 2/23

7:00 am-8:40 pm

1 stop12h 40m

Santiago de los Caballeros

sex 2/27

6:35 am-10:55 pm

1 stop17h 20m

$518

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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, October is the cheapest month in which you can book a flight from Chesapeake to Santiago de los Caballeros (average of $171). Flying from Chesapeake to Santiago de los Caballeros in May is currently the most expensive (average of $434). 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 outubro 29, 2025.
See what other customers who have flown with Delta, United Airlines, and American 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.
Delta
7.9
Good
7,992 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,992 reviews
Delta
7.9
Good
7,992 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,999 reviews
Delta
7.9
Good
7,992 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,030 reviews
Delta
7.9
Good
7,992 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Spirit Airlines
6.3
Okay
8,114 reviews
Delta
7.9
Good
7,992 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 5 different airlines.

  • How long is the flight from Chesapeake to Santiago de los Caballeros?

    Spirit Airlines and American Airlines can get you from Chesapeake to Santiago de los Caballeros in just under 5h 31m. Your travel time can differ by up to 4h 01m. The distance between Chesapeake and Santiago de los Caballeros is about 1254 mi. This flight may include one or multiple stops.

  • 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, October is the cheapest month in which you can book a flight from Chesapeake to Santiago de los Caballeros (average of $171). Flying from Chesapeake to Santiago de los Caballeros in May is currently the most expensive (average of $434). 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 5 airlines flying from Chesapeake to Santiago de los Caballeros

Discover the top 5 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 outubro 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$293Average$521FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$346Average$640FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$374Average$613FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$410Average$660FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$454Average$678FlexibilityNo cancel feeOn-time69%

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