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Islip

$84+ Cheap flights from Chicago (CHI) to Islip (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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ISP
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$168
(Frontier)

One-way from

$84
(Cheapflightsfares)

Popular in

October

Cheapest in

March

Average price

$366
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. 11% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This Frontier deal was found by Cheapflights users on 9/15. 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 9/298:49 pmORD - ISP
1 stop12h 51mFrontier
Thu 10/211:40 amISP - ORD
1 stop9h 04mFrontier
Deal found 9/15$168
This Frontier deal was found by Cheapflights users on 9/14. 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.
Thu 10/28:05 amORD - ISP
1 stop7h 22mFrontier
Sun 10/59:49 amISP - ORD
2 stops14h 31mFrontier
Deal found 9/14$206
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/295:17 pmORD - ISP
1 stop16h 23mMultiple Airlines
Fri 10/35:05 pmISP - ORD
1 stop24h 07mMultiple Airlines
Deal found 9/14$217
This Frontier deal was found by Cheapflights users on 9/14. 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.
Thu 9/188:05 amORD - ISP
1 stop7h 22mFrontier
Thu 9/2511:40 amISP - ORD
1 stop9h 04mFrontier
Deal found 9/14$224
This Frontier deal was found by Cheapflights users on 9/16. 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.
Thu 11/63:18 pmORD - ISP
2 stops16h 36mFrontier
Sat 11/811:40 amISP - ORD
2 stops12h 49mFrontier
Deal found 9/16$229
This Frontier deal was found by Cheapflights users on 9/13. 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.
Fri 9/268:49 pmORD - ISP
1 stop13h 06mFrontier
Sun 9/2811:25 amISP - ORD
1 stop9h 19mFrontier
Deal found 9/13$240
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/76:00 amORD - ISP
1 stop13h 42mMultiple Airlines
Wed 10/84:58 pmISP - ORD
1 stop16h 16mMultiple Airlines
Deal found 9/14$249
This Frontier deal was found by Cheapflights users on 9/15. 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.
Sun 9/288:49 pmORD - ISP
1 stop12h 51mFrontier
Sun 10/511:25 amISP - ORD
1 stop9h 19mFrontier
Deal found 9/15$256
This Frontier deal was found by Cheapflights users on 9/14. 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.
Thu 10/305:50 pmORD - ISP
2 stops15h 47mFrontier
Mon 11/39:54 amISP - ORD
2 stops15h 17mFrontier
Deal found 9/14$268

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 September 16, 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

Mon 9/29

8:49 pm-10:40 am

1 stop12h 51m

Islip Long Island

Thu 10/2

11:40 am-7:44 pm

1 stop9h 04m

$168

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 10/2

8:05 am-4:27 pm

1 stop7h 22m

Islip Long Island

Sun 10/5

9:49 am-11:20 pm

2 stops14h 31m

$206

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 9/29

5:17 pm-10:40 am

1 stop16h 23m

Islip Long Island

Fri 10/3

5:05 pm-4:12 pm

1 stop24h 07m

$217

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Fri 10/3

8:49 pm-10:55 am

1 stop13h 06m

Islip Long Island

Sun 10/5

11:25 am-7:44 pm

1 stop9h 19m

$224

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 11/6

3:18 pm-8:54 am

2 stops16h 36m

Islip Long Island

Sat 11/8

11:40 am-11:29 pm

2 stops12h 49m

$229

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Fri 9/26

8:49 pm-10:55 am

1 stop13h 06m

Islip Long Island

Sun 9/28

11:25 am-7:44 pm

1 stop9h 19m

$240

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Tue 10/7

6:00 am-8:42 pm

1 stop13h 42m

Islip Long Island

Wed 10/8

4:58 pm-8:14 am

1 stop16h 16m

$249

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sun 9/28

8:49 pm-10:40 am

1 stop12h 51m

Islip Long Island

Sun 10/5

11:25 am-7:44 pm

1 stop9h 19m

$256

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 10/2

8:05 am-4:27 pm

1 stop7h 22m

$84

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 9/22

8:49 pm-10:40 am

1 stop12h 51m

$90

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 16 results
1
2

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?

Currently, January is the cheapest month in which you can book a flight from Chicago to Islip (average of $108). Flying from Chicago to Islip 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 September 16, 2025.

It’s typically best to fly out from Chicago to Islip 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 September 16, 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
4,242 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chicago to Islip?

    Departing from Chicago to Islip will take you 12h 51m. The distance from Chicago to Islip is about 770 mi.

  • What is the cheapest airline to fly from Chicago to Islip round-trip?

    Cheapflights users have booked flights from Chicago to Islip round-trip from $254. You may be able to fly from Chicago to Islip for 31% less than the average price by searching for this airline.

  • 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?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Islip (average of $108). Flying from Chicago to Islip 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?

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

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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$254Average$371FlexibilityNo cancel feeOn-time63%

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