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Islip

$109+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ISP
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$225
(FlightHub)

One-way from

$109
(Frontier)

Popular in

July

Cheapest in

March

Average price

$446
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. 3% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 31, 2025.

This Frontier deal was found by Cheapflights users on 7/30. 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.
mié. 8/1311:28 amORD - ISP
1 stop7h 24mFrontier
jue. 8/146:00 amISP - ORD
1 stop10h 27mFrontier
Deal found 7/30$228
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/101:50 pmORD - ISP
1 stop7h 15mSouthwest
dom. 9/146:00 amISP - ORD
1 stop6h 50mSouthwest
Deal found 7/29$302
This Mytrip deal was found by Cheapflights users on 7/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/45:17 pmORD - ISP
2 stops25h 50mMultiple Airlines
dom. 9/72:19 pmISP - ORD
3 stops32h 39mMultiple Airlines
Deal found 7/31$586

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 julio 31, 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

mié. 8/13

11:28 am-7:52 pm

1 stop7h 24m

Islip Long Island

jue. 8/14

6:00 am-3:27 pm

1 stop10h 27m

$228

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

mié. 9/10

1:50 pm-10:05 pm

1 stop7h 15m

Islip Long Island

dom. 9/14

6:00 am-11:50 am

1 stop6h 50m

$302

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

jue. 9/4

5:17 pm-8:07 pm

2 stops25h 50m

Islip Long Island

dom. 9/7

2:19 pm-9:58 pm

3 stops32h 39m

$586

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

mar. 8/12

11:28 am-9:58 pm

1 stop9h 30m

$109

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

sáb. 12/6

1:45 pm-9:45 pm

2 stops7h 00m

$146

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

sáb. 12/6

10:15 am-11:00 am

3 stops23h 45m

$251

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 julio 31, 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.

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 julio 31, 2025.
Read through reviews of airlines operating flights from Chicago to Islip, such as Southwest and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 1 airline. 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 ($225), and Southwest ($302) offers the cheapest pricing from Chicago to Islip, New York. Frontier is currently priced 34% below the average price you’ll pay for this route.

  • 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.

See more FAQs

Traveling to a place near Islip?

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Alternative routes for Chicago to Islip

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Chicago to Islip

Discover the top airline that operate flights from Chicago 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$254Average$371FlexibilityNo cancel feeOn-time63%

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