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Islip

$88+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ISP
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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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 December 23, 2025.

This CheapOair deal was found by Cheapflights users on 12/21. 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.
Wed 12/3111:23 amORD - ISP
1 stop23h 02mFrontier
Fri 1/28:35 pmISP - ORD
1 stop13h 32mFrontier
Deal found 12/21$513
This CheapOair deal was found by Cheapflights users on 12/21. 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.
Sun 12/288:09 pmORD - ISP
1 stop16h 00mFrontier
Mon 12/298:35 pmISP - ORD
1 stop13h 27mFrontier
Deal found 12/21$602
This CheapOair deal was found by Cheapflights users on 12/21. 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.
Sun 12/288:09 pmORD - ISP
1 stop16h 00mFrontier
Wed 12/315:27 pmISP - ORD
1 stop17h 51mFrontier
Deal found 12/21$612
This CheapOair deal was found by Cheapflights users on 12/22. 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 12/307:01 pmORD - ISP
1 stop20h 36mFrontier
Thu 1/112:20 pmISP - ORD
1 stop21h 32mFrontier
Deal found 12/22$672
This CheapOair deal was found by Cheapflights users on 12/22. 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.
Wed 12/2411:23 amORD - ISP
1 stop23h 02mFrontier
Tue 1/612:55 pmISP - ORD
1 stop28h 24mFrontier
Deal found 12/22$702
This Frontier deal was found by Cheapflights users on 12/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/229:47 amORD - ISP
1 stop8h 53mFrontier
Mon 12/298:35 pmISP - ORD
1 stop13h 27mFrontier
Deal found 12/21$711
This CheapOair deal was found by Cheapflights users on 12/22. 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 12/299:47 amORD - ISP
1 stop24h 38mFrontier
Wed 12/315:27 pmISP - ORD
1 stop17h 51mFrontier
Deal found 12/22$727
This CheapOair deal was found by Cheapflights users on 12/21. 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 12/265:18 pmORD - ISP
1 stop29h 41mFrontier
Wed 12/315:27 pmISP - ORD
1 stop17h 51mFrontier
Deal found 12/21$732
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/2212:39 pmORD - ISP
2 stops21h 46mMultiple Airlines
Tue 12/234:40 pmISP - ORD
1 stop26h 59mMultiple Airlines
Deal found 12/21$769
This CheapOair deal was found by Cheapflights users on 12/21. 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.
Wed 12/3111:23 amORD - ISP
1 stop23h 02mFrontier
Sun 1/42:04 pmISP - ORD
1 stop19h 43mFrontier
Deal found 12/21$772
This CheapOair deal was found by Cheapflights users on 12/22. 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 12/2310:12 amORD - ISP
1 stop29h 25mFrontier
Tue 12/3012:20 pmISP - ORD
1 stop22h 58mFrontier
Deal found 12/22$777
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/2212:39 pmORD - ISP
2 stops10h 20mMultiple Airlines
Mon 12/294:40 pmISP - ORD
1 stop8h 50mMultiple Airlines
Deal found 12/21$778

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 December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$165
(CheapOair)

One-way from

$88
(CheapOair)

Popular in

June

Cheapest in

January

Average price

$236
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. 5% potential increase in price ($13 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 December 2025
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 December 23, 2025.
Use the filters below to find and compare flights from Chicago to Islip that are best for you.

Fly from

Chicago

Fly to

Islip

Route

Depart

Return

Price

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Fri 1/30

12:44 pm-8:47 pm

1 stop7h 03m

Islip Long Island

Sun 2/1

7:53 pm-9:03 pm

2 stops26h 10m

$201

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 1/26

7:20 am-6:48 pm

2 stops10h 28m

Islip Long Island

Tue 1/27

12:45 pm-10:04 pm

1 stop10h 19m

$234

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 1/5

12:25 pm-11:59 pm

1 stop10h 34m

Islip Long Island

Thu 1/8

8:40 pm-7:17 pm

1 stop23h 37m

$243

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Fri 1/30

11:45 am-8:47 pm

1 stop8h 02m

Islip Long Island

Sun 2/1

9:25 am-10:41 am

1 stop26h 16m

$252

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 2/9

7:00 am-6:40 pm

1 stop10h 40m

Islip Long Island

Thu 2/12

11:55 am-8:12 pm

2 stops33h 17m

$260

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Tue 1/6

4:55 pm-6:55 pm

1 stop25h 00m

Islip Long Island

Sat 1/10

7:56 pm-5:52 pm

1 stop22h 56m

$266

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Wed 1/7

9:19 am-6:55 pm

1 stop8h 36m

Islip Long Island

Sat 1/10

7:56 pm-5:52 pm

1 stop22h 56m

$266

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Fri 4/10

4:00 pm-11:59 pm

1 stop6h 59m

Islip Long Island

Sun 4/12

6:00 am-11:03 pm

1 stop18h 03m

$298

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 1/5

4:55 pm-11:58 am

1 stop18h 03m

Islip Long Island

Fri 1/9

2:01 pm-11:47 am

2 stops22h 46m

$299

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 1/10

8:27 pm-7:45 pm

1 stop22h 18m

$88

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 16 results
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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Islip, New York flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 $37). Flying from Chicago to Islip, New York in July is currently the most expensive (average of $104). 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 CHI to ISP?

Find hourly flight availability from Chicago 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 December 23, 2025.

It’s typically best to fly out from Chicago to Islip, New York in the evening. Doing so could potentially save you 57% on the flight price compared to flying in the morning, which is usually more expensive.

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 December 23, 2025.
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
4,253 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

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
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

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 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 10h 34m. 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 $37). Flying from Chicago to Islip, New York in July is currently the most expensive (average of $104). 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

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Alternative routes for Chicago to Islip

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