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Islip

$96+ Cheap flights from Chicago (CHI) 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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ISP
May 9 — May 161
Sat 5/9
Sat 5/16
1 adult, Economy
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Find cheap flights from Chicago to Islip with Cheapflights

1. Tell us where you want to go

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Cheap flight deals from Chicago to Islip

Cheapest flights from Chicago to Islip
Explore the most affordable flight options available from Chicago to Islip. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 9, 2026.

This CheapOair deal was found by Cheapflights users on 4/5. 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 5/115:30 pm
ORD
-
ISP
1 stop16h 30m
Frontier
Wed 5/1311:00 am
ISP
-
ORD
1 stop13h 13m
Frontier
Deal found 4/5$180
This Kiwi.com deal was found by Cheapflights users on 4/5. 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.
Wed 5/133:55 pm
ORD
-
ISP
1 stop17h 32m
Frontier
Sun 5/1711:12 am
ISP
-
ORD
1 stop13h 01m
Frontier
Deal found 4/5$244
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
Wed 5/133:55 pm
ORD
-
ISP
1 stop17h 32m
Multiple Airlines
Sun 5/177:53 pm
ISP
-
ORD
2 stops37h 02m
Multiple Airlines
Deal found 4/6$271
This Kiwi.com deal was found by Cheapflights users on 4/7. 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.
Wed 5/69:00 am
ORD
-
ISP
2 stops33h 13m
Multiple Airlines
Wed 5/1311:00 am
ISP
-
ORD
1 stop12h 14m
Multiple Airlines
Deal found 4/7$273
This Kiwi.com deal was found by Cheapflights users on 4/8. 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.
Tue 4/218:52 pm
ORD
-
ISP
2 stops13h 18m
Multiple Airlines
Fri 4/248:31 pm
ISP
-
ORD
1 stop23h 23m
Multiple Airlines
Deal found 4/8$327
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 4/171:09 pm
ORD
-
ISP
1 stop21h 01m
Multiple Airlines
Mon 4/204:07 pm
ISP
-
ORD
2 stops19h 16m
Multiple Airlines
Deal found 4/4$328
This Expedia deal was found by Cheapflights users on 4/4. 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.
Sun 4/194:57 pm
ORD
-
ISP
1 stop15h 16m
Frontier
Thu 4/238:31 pm
ISP
-
ORD
1 stop28h 56m
Frontier
Deal found 4/4$330
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 4/242:09 pm
ORD
-
ISP
1 stop20h 01m
Multiple Airlines
Sun 4/268:35 pm
ISP
-
ORD
1 stop22h 45m
Multiple Airlines
Deal found 4/5$331
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 5/168:30 am
ORD
-
ISP
1 stop8h 28m
Multiple Airlines
Sat 5/2311:57 am
ISP
-
ORD
2 stops25h 26m
Multiple Airlines
Deal found 4/5$337

Find flight deals from Chicago to Islip

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Islip (ISP). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$180
(CheapOair)

One-way from

$96
(CheapOair)

Popular in

March

Cheapest in

January

Average price

$229
Provider with most accurate pricing for Chicago (CHI)-Islip Long Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Islip Long Island flights.
Search Deals
From Chicago (CHI) to Islip Long Island
Search Deals
One-way flight from Chicago (CHI) to Islip Long Island
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 April 9, 2026.
Use the filters below to find and compare flights from Chicago to Islip that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 5/11

5:30 pm-11:00 am

1 stop16h 30m

Islip Long Island

Wed 5/13

11:00 am-11:13 pm

1 stop13h 13m

$180

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Wed 5/13

3:55 pm-10:27 am

1 stop17h 32m

Islip Long Island

Sun 5/17

7:53 pm-7:55 am

2 stops37h 02m

$271

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Wed 5/6

9:00 am-7:13 pm

2 stops33h 13m

Islip Long Island

Wed 5/13

11:00 am-10:14 pm

1 stop12h 14m

$273

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Wed 5/6

11:55 am-10:10 pm

2 stops9h 15m

Islip Long Island

Wed 5/13

6:30 am-4:05 pm

2 stops10h 35m

$345

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 5/16

5:30 pm-10:27 am

1 stop15h 57m

Islip Long Island

Sat 5/23

11:00 am-11:13 pm

1 stop13h 13m

$351
Quickest round-trip

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 6/1

3:05 pm-10:30 pm

1 stop6h 25m

Islip Long Island

Wed 6/3

6:55 am-6:25 pm

1 stop12h 30m

$360

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 5/23

3:15 pm-10:40 pm

1 stop6h 25m

Islip Long Island

Tue 5/26

6:55 am-6:25 pm

1 stop12h 30m

$360

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Fri 5/29

10:49 am-10:05 am

1 stop22h 16m

Islip Long Island

Sun 5/31

11:00 am-11:13 pm

1 stop13h 13m

$361
Cheapest one-way

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 5/4

4:28 pm-10:05 am

2 stops40h 37m

$121

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sun 4/26

5:50 am-7:36 pm

2 stops36h 46m

$145

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/5

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

Compare providers for flights from Chicago to Islip

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Islip in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Islip, New York flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Islip, New York flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Islip, New York flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Islip, New York flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Islip, New York flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Islip

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

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Islip, New York (average of $34). Flying from Chicago to Islip, New York in July is currently the most expensive (average of $93). 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 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 April 9, 2026.
Read through reviews of airlines operating flights from Chicago to Islip, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,338 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,338 reviews
Southwest
8.0
Very good
4,338 reviews

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 Chicago?

    Most people fly into Islip Long Island (ISP) if they book a flight to Islip from Chicago. On average, Long Island has 0 inbound flights from Chicago per day from 0 airlines. Islip Long Island is conveniently located just 7.2 mi from Islip’s city center.

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

    There are many flights that can get you from Chicago to Islip, New York in 16h 30m. Fly via Frontier to get the fastest option. There are 770 mi between Chicago and Islip, New York.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago to Islip, New York (average of $34). Flying from Chicago to Islip, New York in July is currently the most expensive (average of $93). 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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