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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 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ISP
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheap 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 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$181
(CheapOair)

One-way from

$88
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$206
Provider with most accurate pricing for Chicago (CHI)-Islip Long Island flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Islip Long Island flights.
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From Chicago (CHI) to Islip Long Island
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One-way flight from Chicago (CHI) to Islip Long Island
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Highest demand for flights based on searches. 8% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find 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 24, 2025.

This CheapOair deal was found by Cheapflights users on 4/22. 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 5/285:03 pmORD - ISP
1 stop25h 23mFrontier
Sat 5/319:06 pmISP - ORD
1 stop28h 30mFrontier
Deal found 4/22$181
This Southwest deal was found by Cheapflights users on 4/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/131:50 pmORD - ISP
1 stop8h 00mSouthwest
Wed 5/147:30 amISP - ORD
1 stop6h 35mSouthwest
Deal found 4/22$308
This Trip.com deal was found by Cheapflights users on 4/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/75:08 pmORD - ISP
1 stop25h 33mMultiple Airlines
Sat 6/148:21 pmISP - ORD
2 stops18h 15mMultiple Airlines
Deal found 4/23$355
This KAYAK deal was found by Cheapflights users on 4/23. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/127:31 pmORD - ISP
1 stop24h 57mJetBlue
Thu 5/156:00 amISP - ORD
1 stop13h 36mJetBlue
Deal found 4/23$424

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 24, 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

Wed 5/28

5:03 pm-7:26 pm

1 stop25h 23m

Islip Long Island

Sat 5/31

9:06 pm-12:36 am

1 stop28h 30m

$181

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Tue 5/13

1:50 pm-10:50 pm

1 stop8h 00m

Islip Long Island

Wed 5/14

7:30 am-1:05 pm

1 stop6h 35m

$308

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 6/7

5:08 pm-7:41 pm

1 stop25h 33m

Islip Long Island

Sat 6/14

8:21 pm-1:36 pm

2 stops18h 15m

$355

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 5/12

7:31 pm-9:28 pm

1 stop24h 57m

Islip Long Island

Thu 5/15

6:00 am-6:36 pm

1 stop13h 36m

$424

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 5/31

1:02 pm-8:42 pm

1 stop6h 40m

$88

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 5/12

7:31 pm-9:28 pm

1 stop24h 57m

$201

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 6/21

12:40 pm-11:10 pm

2 stops9h 30m

$209

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 5/24

4:35 pm-6:59 pm

3 stops25h 24m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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*
FlightHubPrice Accuracy3 starsTrust Score*2 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust 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 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 $108). Flying from Chicago 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 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 April 24, 2025.

It’s typically best to fly out from Chicago to Islip, New York at noon. Doing so could potentially save you 62% on the flight price compared to flying in the morning, which is usually more expensive.

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 April 24, 2025.
Read reviews from past customers who have flown Southwest, JetBlue and Frontier from Chicago to Islip. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,283 reviews
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

  • What are the cheapest airlines flying from Chicago to Islip, New York round-trip?

    According to our current data, Frontier ($181), Southwest ($308), and JetBlue ($424) offers the cheapest pricing from Chicago to Islip, New York.

  • What are the cheapest airlines to fly from Chicago to Islip, New York one-way?

    $88 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on JetBlue and Southwest, with prices starting from $201 and $209, respectively.

  • 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 $108). Flying from Chicago 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.

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