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Islip

$54+ Cheap flights from Chesapeake, VA to Islip, NY (ISP)

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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ISP
nov. 28 — dic. 51
vie. 11/28
vie. 12/5
1 adult, Economy
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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 octubre 29, 2025.

This Breeze Airways deal was found by Cheapflights users on 10/26. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/118:43 amORF - ISP
Nonstop1h 15mBreeze Airways
dom. 12/1410:38 amISP - ORF
Nonstop1h 20mBreeze Airways
Deal found 10/26$123
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/29:26 pmORF - ISP
1 stop25h 18mMultiple Airlines
jue. 12/410:38 amISP - ORF
Nonstop1h 20mMultiple Airlines
Deal found 10/28$131
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/29:26 pmORF - ISP
1 stop25h 18mMultiple Airlines
dom. 12/710:38 amISP - ORF
Nonstop1h 20mMultiple Airlines
Deal found 10/28$144
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/135:41 pmORF - ISP
Nonstop1h 15mBreeze Airways
dom. 11/167:36 pmISP - ORF
Nonstop1h 20mBreeze Airways
Deal found 10/28$147
This Breeze Airways 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/65:41 pmORF - ISP
Nonstop1h 15mBreeze Airways
dom. 11/97:36 pmISP - ORF
Nonstop1h 20mBreeze Airways
Deal found 10/29$158
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/118:43 amORF - ISP
Nonstop1h 15mMultiple Airlines
dom. 12/1411:15 amISP - ORF
1 stop20h 28mMultiple Airlines
Deal found 10/26$161
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/132:00 pmORF - ISP
1 stop20h 37mMultiple Airlines
dom. 11/167:36 pmISP - ORF
Nonstop1h 20mMultiple Airlines
Deal found 10/28$164
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/126:33 pmORF - ISP
1 stop23h 09mMultiple Airlines
dom. 11/167:36 pmISP - ORF
Nonstop1h 20mMultiple Airlines
Deal found 10/28$169

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 octubre 29, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$123
(Breeze Airways)

One-way from

$54
(Breeze Airways)

Popular in

February

Cheapest in

May

Average price

$193
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
One-way flight from Chesapeake to Islip Long Island
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
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 octubre 29, 2025.
Use the filters below to find and compare flights from Chesapeake to Islip that are best for you.

Fly from

Chesapeake

Fly to

Islip

Route

Depart

Return

Price

NorfolkIslip

ORF - ISP

ORFISP

Norfolk

jue. 12/11

8:43 am-9:58 am

Nonstop1h 15m

Islip Long Island

dom. 12/14

10:38 am-11:58 am

Nonstop1h 20m

$123

NorfolkIslip

ORF - ISP

ORFISP

Norfolk

mar. 12/2

9:26 pm-10:44 pm

1 stop25h 18m

Islip Long Island

jue. 12/4

10:38 am-11:58 am

Nonstop1h 20m

$131

NorfolkIslip

ORF - ISP

ORFISP

Norfolk

mar. 12/2

9:26 pm-10:44 pm

1 stop25h 18m

Islip Long Island

dom. 12/7

10:38 am-11:58 am

Nonstop1h 20m

$144

NorfolkIslip

ORF - ISP

ORFISP

Norfolk

jue. 11/13

5:41 pm-6:56 pm

Nonstop1h 15m

Islip Long Island

dom. 11/16

7:36 pm-8:56 pm

Nonstop1h 20m

$147

NorfolkIslip

ORF - ISP

ORFISP

Norfolk

jue. 12/11

8:43 am-9:58 am

Nonstop1h 15m

Islip Long Island

dom. 12/14

11:15 am-7:43 am

1 stop20h 28m

$161

NorfolkIslip

ORF - ISP

ORFISP

Norfolk

jue. 11/13

2:00 pm-10:37 am

1 stop20h 37m

Islip Long Island

dom. 11/16

7:36 pm-8:56 pm

Nonstop1h 20m

$164

NorfolkIslip

ORF - ISP

ORFISP

Norfolk

mié. 11/12

6:33 pm-5:42 pm

1 stop23h 09m

Islip Long Island

dom. 11/16

7:36 pm-8:56 pm

Nonstop1h 20m

$169

NorfolkIslip

ORF - ISP

ORFISP

Norfolk

vie. 11/14

4:57 pm-10:37 am

1 stop17h 40m

Islip Long Island

dom. 11/16

7:36 pm-8:56 pm

Nonstop1h 20m

$189

NorfolkIslip

ORF - ISP

ORFISP

Norfolk

jue. 11/27

5:41 pm-6:56 pm

Nonstop1h 15m

$54

NorfolkIslip

ORF - ISP

ORFISP

Norfolk

mié. 11/26

9:26 pm-9:07 am

1 stop11h 41m

$95

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 17 results
1
2

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.

Cheapflights Insights

Everything you need to know about your flight from Chesapeake to Islip

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

Currently, February is the cheapest month in which you can book a flight from Chesapeake to Islip, New York (average of $78). Flying from Chesapeake to Islip, New York in April is currently the most expensive (average of $157). 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 octubre 29, 2025.

When flying from Chesapeake to Islip, New York, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 64% versus a flight at noon.

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 octubre 29, 2025.
Get a feel of what it's like to fly with Breeze Airways and Southwest from Chesapeake to Islip by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
221 reviews

Boarding

8.3

Crew

8.7

Comfort

8.2

Entertainment

6.6

Overall

8.1

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.1
Very good
221 reviews
Breeze Airways
8.1
Very good
221 reviews

Boarding

8.3

Crew

8.7

Comfort

8.2

Entertainment

6.6

Overall

8.1

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Southwest
8.0
Very good
4,241 reviews
Breeze Airways
8.1
Very good
221 reviews

Boarding

8.3

Crew

8.7

Comfort

8.2

Entertainment

6.6

Overall

8.1

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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.

  • How long is the flight from Chesapeake to Islip, New York?

    There are many flights that can get you from Chesapeake to Islip, New York in 1h 15m. Fly via Breeze Airways to get the fastest option. Chesapeake and Islip, New York are separated by a distance of 316 mi. Generally, flights for this route are nonstop.

  • 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, February is the cheapest month in which you can book a flight from Chesapeake to Islip, New York (average of $78). Flying from Chesapeake to Islip, New York in April is currently the most expensive (average of $157). 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 Islip?

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

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Alternative routes for Chesapeake to Islip

See prices for flight routes from nearby airports that may be better suited for you.
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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 octubre 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$78Average$132FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$152Average$351FlexibilityNo cancel feeOn-time63%

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