HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Islip

$127+ Cheap flights from Chesapeake, VA to Islip, NY (ISP)

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 3/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ISP
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chesapeake to Islip with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chesapeake to Islip

Keep the following information in mind while searching for Chesapeake to Islip flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$127
(Expedia)

Popular in

February

Cheapest in

May

Average price

$366
Provider with most accurate pricing for Norfolk-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-New York (NYC) flights.
Search Deals
From Chesapeake to Islip Long Island
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals

Find flight deals from Chesapeake to Islip

Cheapest flights from Chesapeake to Islip
Explore the most affordable flight options available from Chesapeake to Islip. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Expedia deal was found by Cheapflights users on 2/19. 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.
Sat 3/159:05 amORF - ISP
1 stop10h 59mMultiple Airlines
Sun 3/2310:50 amISP - ORF
Nonstop1h 22mMultiple Airlines
Deal found 2/19$127
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/86:35 pmORF - ISP
1 stop5h 15mSouthwest
Tue 3/114:20 pmISP - ORF
1 stop6h 15mSouthwest
Deal found 2/20$270
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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.
Thu 6/125:45 pmORF - ISP
Nonstop1h 14mBreeze Airways
Sun 6/157:39 pmISP - ORF
Nonstop1h 21mBreeze Airways
Deal found 2/20$370

Find flights from Chesapeake to Islip within your budget

Customize your flight search to find flights from Chesapeake to Islip 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 February 20, 2025.

Fly from

Chesapeake

Fly to

Islip

Route

Depart

Return

Price

NorfolkIslip

ORF - ISP

ORFISP

Norfolk

Sat 3/15

9:05 am-8:04 pm

1 stop10h 59m

Islip Long Island

Sun 3/23

10:50 am-12:12 pm

Nonstop1h 22m

$127

NorfolkIslip

ORF - ISP

ORFISP

Norfolk

Sat 3/8

6:35 pm-11:50 pm

1 stop5h 15m

Islip Long Island

Tue 3/11

4:20 pm-10:35 pm

1 stop6h 15m

$270

NorfolkIslip

ORF - ISP

ORFISP

Norfolk

Thu 6/12

5:45 pm-6:59 pm

Nonstop1h 14m

Islip Long Island

Sun 6/15

7:39 pm-9:00 pm

Nonstop1h 21m

$370

NorfolkIslip

ORF - ISP

ORFISP

Norfolk

Sun 3/9

8:57 am-10:11 am

Nonstop1h 14m

$180

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Best time to book a flight from Chesapeake to Islip

Have a flexible travel schedule? Discover the best time to fly to Islip 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.

Travel insights for flights from Chesapeake to Islip

Get recent, data-driven insights about flights from Chesapeake to Islip including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chesapeake to Islip, New York?

Currently, January is the cheapest month in which you can book a flight from Chesapeake to Islip, New York (average of $108). Flying from Chesapeake to Islip, New York in November is currently the most expensive (average of $213). 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.

What is the cheapest time of day to fly from C6E to ISP?

Find hourly flight availability from Chesapeake to Islip. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chesapeake to Islip, New York as you normally would.

Rainfall in Islip by month

Plan your trip to Islip by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Islip, New York ranges from 3.3 - 4.4 inches per month. March is typically the wettest month, when rainfall can reach 4.4 in. February is typically the driest time to visit Islip, New York when rainfall is around 3.3 in.

Temperature in Islip by month

Plan your trip to Islip by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Islip, New York, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

Reviews of airlines servicing Islip

Get insights into the airlines that provide service to Islip. 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 Islip. Reviews last updated February 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Breeze Airways
8.1
Very good
150 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

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

    Islip Long Island (ISP) is the airport you will fly into if you book a flight from Chesapeake to Islip. You should not have trouble finding flights to Long Island from Chesapeake; the airport handles an average of 0 inbound flights from Chesapeake per day. You should also have plenty of airline options to choose from since 2 airlines have flights to the Islip airport from Chesapeake. It is only a 7.2 mi journey from Long Island (ISP) to Islip’s city center.

  • How popular is this Chesapeake to Islip, New York flight route?

    Within the past month, 1 users have taken a look at flights from Chesapeake to Islip Long Island.

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

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

  • How can I find direct flights from Chesapeake to Islip?

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

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

    Yes. Cheapflights offers flight deals from Chesapeake to Islip 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 Islip, New York?

    Currently, January is the cheapest month in which you can book a flight from Chesapeake to Islip, New York (average of $108). Flying from Chesapeake to Islip, New York in November is currently the most expensive (average of $213). 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

Traveling to a place near Chesapeake?

Book flights to Chesapeake if you plan to visit one of these locations
Southampton
Riverhead

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 Islip

See prices for flight routes from nearby airports that may be better suited for you.
Raleigh to John F Kennedy Intl flights
Raleigh to LaGuardia flights
Raleigh to Newark flights
Dulles Intl to John F Kennedy Intl flights
Richmond to John F Kennedy Intl flights
Dulles Intl to Newark flights
Richmond to LaGuardia flights
Reagan-National to John F Kennedy Intl flights
Reagan-National to LaGuardia flights
Richmond to Newark flights
Reagan-National to Newark flights
Dulles Intl to LaGuardia flights
Norfolk to John F Kennedy Intl flights
Greensboro to LaGuardia flights
Raleigh to Islip flights
Greensboro to Newark flights
Norfolk to LaGuardia flights
Greensboro to John F Kennedy Intl flights
Norfolk to Newark flights
Dulles Intl to Albany flights
Dulles Intl to Syracuse flights
Dulles Intl to Buffalo flights
Reagan-National to Syracuse flights
Raleigh to White Plains flights
Reagan-National to Buffalo flights
Reagan-National to Albany flights
Charlottesville to LaGuardia flights
Dulles Intl to Rochester flights
Charlottesville to John F Kennedy Intl flights
Reagan-National to White Plains flights
Raleigh to Buffalo flights
Dulles Intl to White Plains flights
Roanoke to John F Kennedy Intl flights
Charlottesville to Newark flights
Reagan-National to Rochester flights
Raleigh to Stewart flights
Roanoke to LaGuardia flights
Raleigh to Syracuse flights
Roanoke to Newark flights
Raleigh to Albany flights
Raleigh to Rochester flights
Dulles Intl to Ithaca flights
Reagan-National to Ithaca flights
Blountville to John F Kennedy Intl flights
Blountville to Newark flights
Richmond to Stewart flights
Blountville to LaGuardia flights
Norfolk to Buffalo flights
Richmond to Buffalo flights
Richmond to Albany flights

Top 2 airlines flying from Chesapeake to Islip

Discover the top 2 airlines that operate flights from Chesapeake to Islip. 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$78Average$166FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$237Average$346FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.