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Santiago de los Caballeros

$377+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — STI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$326
(Priceline)

Popular in

April

Cheapest in

June

Average price

$489
From Chesapeake to Santiago de los Caballeros
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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 September 15, 2025.

This Priceline deal was found by Cheapflights users on 9/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/265:20 amORF - STI
1 stop5h 43mSpirit Airlines
Sat 10/412:10 pmSTI - ORF
1 stop10h 38mSpirit Airlines
Deal found 9/12$377
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2612:19 pmORF - STI
2 stops22h 44mMultiple Airlines
Sat 10/412:10 pmSTI - ORF
1 stop10h 38mMultiple Airlines
Deal found 9/12$412
This Delta deal was found by Cheapflights users on 9/14. 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.
Fri 9/267:10 amORF - STI
1 stop12h 01mDelta
Mon 9/298:40 pmSTI - ORF
2 stops15h 49mDelta
Deal found 9/14$539
This Delta deal was found by Cheapflights users on 9/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1812:13 pmORF - STI
1 stop12h 21mDelta
Mon 9/228:40 pmSTI - ORF
2 stops15h 49mDelta
Deal found 9/13$559
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Fri 9/267:27 pmORF - STI
2 stops17h 00mAmerican Airlines
Sat 10/41:29 pmSTI - ORF
2 stops21h 34mAmerican Airlines
Deal found 9/14$602
This American Airlines deal was found by Cheapflights users on 9/13. 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.
Fri 9/267:27 pmORF - STI
2 stops17h 00mAmerican Airlines
Mon 9/291:29 pmSTI - ORF
2 stops20h 47mAmerican Airlines
Deal found 9/13$612
This Expedia deal was found by Cheapflights users on 9/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2610:23 amORF - STI
2 stops16h 05mJetBlue
Fri 10/33:20 amSTI - ORF
2 stops29h 24mJetBlue
Deal found 9/12$631

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 September 15, 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 9/26

5:20 am-11:03 am

1 stop5h 43m

Santiago de los Caballeros

Sat 10/4

12:10 pm-10:48 pm

1 stop10h 38m

$377

NorfolkSantiago de los Caballeros

ORF - STI

ORFSTI

Norfolk

Fri 9/26

12:19 pm-11:03 am

2 stops22h 44m

Santiago de los Caballeros

Sat 10/4

12:10 pm-10:48 pm

1 stop10h 38m

$412

NorfolkSantiago de los Caballeros

ORF - STI

ORFSTI

Norfolk

Mon 2/23

7:00 am-6:46 pm

1 stop10h 46m

Santiago de los Caballeros

Fri 2/27

6:35 am-10:55 pm

1 stop17h 20m

$517

NorfolkSantiago de los Caballeros

ORF - STI

ORFSTI

Norfolk

Fri 9/26

12:13 pm-12:34 am

1 stop12h 21m

Santiago de los Caballeros

Sat 10/4

6:11 am-6:42 pm

2 stops12h 31m

$539

NorfolkSantiago de los Caballeros

ORF - STI

ORFSTI

Norfolk

Fri 9/26

7:10 am-7:11 pm

1 stop12h 01m

Santiago de los Caballeros

Mon 9/29

8:40 pm-12:29 pm

2 stops15h 49m

$539

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

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 $600). 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 September 15, 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
8.0
Very good
7,956 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,956 reviews
Delta
8.0
Very good
7,956 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,931 reviews
Delta
8.0
Very good
7,956 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,956 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,016 reviews
Delta
8.0
Very good
7,956 reviews

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

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

    Spirit Airlines and Delta can get you from Chesapeake to Santiago de los Caballeros in just under 5h 43m. Your travel time can differ by up to 5h 03m. 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, 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 $600). 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$293Average$521FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$346Average$640FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$454Average$649FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$454Average$684FlexibilityNo cancel feeOn-time71%

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