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Dominican Republic

$114+ Cheap flights from Chesapeake, VA to the Dominican Republic

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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PUJ
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Chesapeake to Dominican Republic

Cheapest flights from Chesapeake to Dominican Republic
Explore the most affordable flight options available from Chesapeake to Dominican Republic. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/148:41 pm
ORF
-
SDQ
1 stop4h 57m
Spirit Airlines
Mon 3/162:59 am
SDQ
-
ORF
1 stop16h 47m
Spirit Airlines
Deal found 1/28$276
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:31 pm
ORF
-
SDQ
1 stop17h 49m
Spirit Airlines
Tue 3/102:32 pm
SDQ
-
ORF
1 stop27h 54m
Spirit Airlines
Deal found 1/28$285
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sat 2/218:44 pm
ORF
-
PUJ
1 stop18h 52m
Multiple Airlines
Sat 2/284:52 pm
PUJ
-
ORF
1 stop18h 45m
Multiple Airlines
Deal found 1/27$286
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:31 pm
ORF
-
STI
1 stop19h 04m
Spirit Airlines
Tue 3/34:40 pm
STI
-
ORF
1 stop26h 46m
Spirit Airlines
Deal found 1/28$287
This CheapOair deal was found by Cheapflights users on 1/27. 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.
Sat 2/218:44 pm
ORF
-
PUJ
1 stop18h 52m
Spirit Airlines
Wed 2/255:47 pm
PUJ
-
ORF
1 stop25h 39m
Spirit Airlines
Deal found 1/27$293
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/207:31 pm
ORF
-
PUJ
1 stop20h 05m
Multiple Airlines
Sat 2/284:52 pm
PUJ
-
ORF
1 stop18h 45m
Multiple Airlines
Deal found 1/27$300
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sat 2/216:45 am
ORF
-
SDQ
1 stop25h 54m
Multiple Airlines
Sat 2/283:32 pm
SDQ
-
ORF
2 stops20h 05m
Multiple Airlines
Deal found 1/27$310
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2112:29 pm
ORF
-
PUJ
2 stops26h 46m
Frontier
Sat 2/284:52 pm
PUJ
-
ORF
1 stop18h 45m
Frontier
Deal found 1/28$312
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2311:39 am
ORF
-
SDQ
2 stops25h 41m
Multiple Airlines
Tue 3/102:32 pm
SDQ
-
ORF
1 stop27h 54m
Multiple Airlines
Deal found 1/28$312
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/207:31 pm
ORF
-
SDQ
1 stop17h 49m
Multiple Airlines
Sat 2/283:32 pm
SDQ
-
ORF
2 stops20h 05m
Multiple Airlines
Deal found 1/27$319
This CheapOair deal was found by Cheapflights users on 1/27. 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.
Fri 3/138:41 pm
ORF
-
STI
1 stop5h 08m
Spirit Airlines
Fri 3/203:43 pm
STI
-
ORF
1 stop28h 03m
Spirit Airlines
Deal found 1/27$327
This CheapOair deal was found by Cheapflights users on 1/26. 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.
Fri 3/138:41 pm
ORF
-
SDQ
1 stop4h 57m
Spirit Airlines
Thu 3/192:59 am
SDQ
-
ORF
1 stop16h 47m
Spirit Airlines
Deal found 1/26$327

Find flight deals from Chesapeake to Dominican Republic

Keep the following information in mind while searching for Chesapeake to Dominican Republic flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$276
(Cheapflightsfares)

One-way from

$114
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$544
Provider with most accurate pricing for Norfolk-Punta Cana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Punta Cana flights.
Search Deals
From Chesapeake to Dominican Republic
Search Deals
One-way flight from Chesapeake to Dominican Republic
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($113 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($37 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to Dominican Republic 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 January 29, 2026.
Use the filters below to find and compare flights from Chesapeake to the Dominican Republic that are best for you.

Fly from

Chesapeake

Fly to

Dominican Republic

Route

Depart

Return

Price

NorfolkSanto Domingo

ORF - SDQ

ORFSDQ

Norfolk

Sat 3/14

8:41 pm-1:38 am

1 stop4h 57m

Santo Domingo Las Americas

Mon 3/16

2:59 am-7:46 pm

1 stop16h 47m

$276

NorfolkSanto Domingo

ORF - SDQ

ORFSDQ

Norfolk

Tue 3/31

8:41 pm-1:38 am

1 stop4h 57m

Santo Domingo Las Americas

Mon 4/6

2:59 am-7:46 pm

1 stop16h 47m

$276

NorfolkSanto Domingo

ORF - SDQ

ORFSDQ

Norfolk

Mon 2/23

7:31 pm-2:20 pm

1 stop17h 49m

Santo Domingo Las Americas

Tue 3/10

2:32 pm-6:26 pm

1 stop27h 54m

$285

NorfolkPunta Cana

ORF - PUJ

ORFPUJ

Norfolk

Sat 2/21

8:44 pm-4:36 pm

1 stop18h 52m

Punta Cana

Sat 2/28

4:52 pm-10:37 am

1 stop18h 45m

$286

NorfolkSantiago de los Caballeros

ORF - STI

ORFSTI

Norfolk

Tue 2/24

7:31 pm-3:35 pm

1 stop19h 04m

Santiago de los Caballeros

Tue 3/3

4:40 pm-6:26 pm

1 stop26h 46m

$287

NorfolkSanto Domingo

ORF - SDQ

ORFSDQ

Norfolk

Sat 2/21

6:45 am-9:39 am

1 stop25h 54m

Santo Domingo Las Americas

Sat 2/28

3:32 pm-10:37 am

2 stops20h 05m

$310

NorfolkSanto Domingo

ORF - SDQ

ORFSDQ

Norfolk

Mon 2/23

11:39 am-2:20 pm

2 stops25h 41m

Santo Domingo Las Americas

Tue 3/10

2:32 pm-6:26 pm

1 stop27h 54m

$312

NorfolkSanto Domingo

ORF - SDQ

ORFSDQ

Norfolk

Fri 2/20

7:31 pm-2:20 pm

1 stop17h 49m

Santo Domingo Las Americas

Sat 2/28

3:32 pm-10:37 am

2 stops20h 05m

$326

NorfolkSantiago de los Caballeros

ORF - STI

ORFSTI

Norfolk

Fri 3/13

8:41 pm-1:49 am

1 stop5h 08m

Santiago de los Caballeros

Fri 3/20

3:43 pm-7:46 pm

1 stop28h 03m

$327

NorfolkSanto Domingo

ORF - SDQ

ORFSDQ

Norfolk

Fri 3/13

8:41 pm-1:38 am

1 stop4h 57m

Santo Domingo Las Americas

Thu 3/19

2:59 am-7:46 pm

1 stop16h 47m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 37 results
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Best time to book a flight from Chesapeake to Dominican Republic

Have a flexible travel schedule? Discover the best time to fly to Dominican Republic 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 the Dominican Republic

What is the cheapest month to book a flight from Chesapeake to Dominican Republic?

Currently, October is the cheapest month in which you can book a flight from Chesapeake to Dominican Republic (average of $171). Flying from Chesapeake to Dominican Republic 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 Dominican Republic

Get insights into the airlines that provide service to Dominican Republic. 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 Dominican Republic. Reviews last updated January 29, 2026.
See what other customers who have flown with Southwest, Delta, and United Airlines from Chesapeake to the Dominican Republic have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,128 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,215 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,205 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,393 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Dominican Republic. 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 Chesapeake to Dominican Republic?

    There are many flights that can get you from Chesapeake to Dominican Republic in 4h 57m. Fly via Spirit Airlines, United Airlines, or American Airlines to get the fastest option. Airlines will cover a distance of 1335 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Chesapeake to Dominican Republic?

    Most travelers choose Norfolk - Punta Cana, Norfolk - Puerto Plata La Union or Norfolk - Santo Domingo Las Americas when deciding on the best route from Chesapeake to Dominican Republic.

  • Can I find deals for flights from Chesapeake to Dominican Republic that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Dominican Republic flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Dominican Republic?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Dominican Republic.

  • Can I find deals for business class flights from Chesapeake to Dominican Republic?

    Yes. Cheapflights offers flight deals from Chesapeake to Dominican Republic 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 Dominican Republic?

    Currently, October is the cheapest month in which you can book a flight from Chesapeake to Dominican Republic (average of $171). Flying from Chesapeake to Dominican Republic 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chesapeake to Dominican Republic

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to Luis Munoz Marin Intl flights
Reagan-National to Luis Munoz Marin Intl flights
Raleigh to Luis Munoz Marin Intl flights
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Richmond to Nassau flights
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Reagan-National to Bridgetown flights
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Richmond to Saint Thomas Island flights
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Dulles Intl to Port of Spain flights
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Richmond to Montego Bay flights
Dulles Intl to Puerto Plata flights
Raleigh to Providenciales flights

Top 6 airlines flying from Chesapeake to Dominican Republic

Discover the top 6 airlines that operate flights from Chesapeake to Dominican Republic. 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$234Average$424FlexibilityNo cancel feeOn-time65%
DeltaCheapest$240Average$577FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$248Average$560FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$289Average$559FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$310Average$594FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$425Average$671FlexibilityNo cancel feeOn-time63%

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