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Santiago de los Caballeros

$210+ Cheap flights from Chesapeake, VA to Santiago de los Caballeros (STI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — STI
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap 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 December 16, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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 12/315:00 amORF - STI
1 stop15h 04mAmerican Airlines
Thu 1/86:00 amSTI - ORF
2 stops18h 05mAmerican Airlines
Deal found 12/16$592
This American Airlines deal was found by Cheapflights users on 12/13. 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.
Tue 12/305:00 amORF - STI
1 stop15h 04mAmerican Airlines
Sat 1/106:00 amSTI - ORF
2 stops17h 46mAmerican Airlines
Deal found 12/13$657
This American Airlines deal was found by Cheapflights users on 12/13. 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 12/145:00 amORF - STI
1 stop14h 33mAmerican Airlines
Mon 12/223:24 pmSTI - ORF
1 stop10h 35mAmerican Airlines
Deal found 12/13$688
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/207:37 pmORF - STI
1 stop20h 50mAmerican Airlines
Sat 12/273:24 pmSTI - ORF
2 stops17h 51mAmerican Airlines
Deal found 12/15$783

Find 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 December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$592
(American Airlines)

One-way from

$210
(Expedia)

Popular in

April

Cheapest in

June

Average price

$578
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.
Search Deals
From Chesapeake to Santiago de los Caballeros
Search Deals
One-way flight from Chesapeake to Santiago de los Caballeros
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($97 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 16, 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

Fri 1/30

10:05 am-11:51 pm

2 stops12h 46m

Santiago de los Caballeros

Fri 2/6

4:00 pm-11:27 pm

1 stop8h 27m

$592

NorfolkSantiago de los Caballeros

ORF - STI

ORFSTI

Norfolk

Wed 12/31

5:00 am-9:04 pm

2 stops15h 04m

Santiago de los Caballeros

Thu 1/8

6:00 am-11:05 pm

2 stops18h 05m

$592

NorfolkSantiago de los Caballeros

ORF - STI

ORFSTI

Norfolk

Sat 1/31

4:10 pm-11:51 pm

1 stop6h 41m

Santiago de los Caballeros

Wed 2/4

4:00 pm-11:27 pm

1 stop8h 27m

$623

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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 July is currently the most expensive (average of $410). 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 December 16, 2025.
See what other customers who have flown with United Airlines, 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.
United Airlines
7.4
Good
9,094 reviews

Entertainment

7.1

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,094 reviews
United Airlines
7.4
Good
9,094 reviews

Entertainment

7.1

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
American Airlines
7.2
Good
11,047 reviews
United Airlines
7.4
Good
9,094 reviews

Entertainment

7.1

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
Spirit Airlines
6.3
Okay
8,188 reviews
United Airlines
7.4
Good
9,094 reviews

Entertainment

7.1

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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?

    United Airlines and American Airlines can get you from Chesapeake to Santiago de los Caballeros in just under 12h 46m. Your travel time can differ by up to 2h 18m. 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 July is currently the most expensive (average of $410). 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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$246Average$494FlexibilityNo cancel feeOn-time65%
DeltaCheapest$370Average$454FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$406Average$575FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$410Average$635FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$464Average$586FlexibilityNo cancel feeOn-time69%

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