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$85+ Cheap flights from Islip, NY (ISP) to Chicago (CHI)

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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — CHI
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap flight deals from Islip to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Islip (ISP) to Chicago (CHI). 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 August 18, 2025.

Round-trip from

$164
(Priceline)

One-way from

$85
(Frontier)

Popular in

July

Cheapest in

April

Average price

$302
From Islip Long Island to Chicago (CHI)
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One-way flight from Islip Long Island to Chicago (CHI)
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Highest demand for flights based on searches. 16% potential increase in price ($75 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Islip to Chicago

Cheapest flights from Islip to Chicago
Explore the most affordable flight options available from Islip to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This Frontier deal was found by Cheapflights users on 8/17. 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 9/2511:40 amISP - ORD
1 stop9h 04mFrontier
Sun 9/288:05 amORD - ISP
1 stop7h 22mFrontier
Deal found 8/17$173
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1711:35 amISP - ORD
1 stop11h 23mMultiple Airlines
Sat 9/205:17 pmORD - ISP
1 stop16h 23mMultiple Airlines
Deal found 8/16$175
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1812:38 pmISP - ORD
1 stop25h 37mFrontier
Sun 10/196:07 pmORD - ISP
1 stop15h 30mFrontier
Deal found 8/17$180
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/85:05 pmISP - ORD
2 stops18h 47mMultiple Airlines
Sat 9/135:17 pmORD - ISP
1 stop16h 23mMultiple Airlines
Deal found 8/16$186
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Sun 9/711:35 amISP - ORD
1 stop29h 37mMultiple Airlines
Mon 9/158:49 pmORD - ISP
1 stop12h 51mMultiple Airlines
Deal found 8/17$193
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/2311:25 amISP - ORD
1 stop11h 33mMultiple Airlines
Mon 9/298:49 pmORD - ISP
1 stop12h 51mMultiple Airlines
Deal found 8/17$195
This Frontier deal was found by Cheapflights users on 8/17. 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 9/2511:40 amISP - ORD
2 stops12h 40mFrontier
Mon 9/298:49 pmORD - ISP
1 stop12h 51mFrontier
Deal found 8/17$197
This Frontier deal was found by Cheapflights users on 8/17. 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 9/59:49 amISP - ORD
2 stops15h 21mFrontier
Thu 9/258:49 pmORD - ISP
1 stop12h 51mFrontier
Deal found 8/17$199
This Frontier deal was found by Cheapflights users on 8/17. 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 9/411:45 amISP - ORD
2 stops12h 35mFrontier
Thu 9/118:05 amORD - ISP
1 stop7h 22mFrontier
Deal found 8/17$200
This Frontier deal was found by Cheapflights users on 8/17. 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 9/79:49 amISP - ORD
2 stops14h 31mFrontier
Mon 9/158:49 pmORD - ISP
1 stop12h 51mFrontier
Deal found 8/17$201
This Frontier deal was found by Cheapflights users on 8/17. 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 9/129:49 amISP - ORD
2 stops13h 56mFrontier
Sun 9/148:49 pmORD - ISP
1 stop12h 51mFrontier
Deal found 8/17$204

Cheapflights Fare Finder

 
Customize your flight search to find flights from Islip to Chicago 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 August 18, 2025.
Use the filters below to find and compare flights from Islip to Chicago that are best for you.

Fly from

Islip

Fly to

Chicago

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 9/4

11:45 am-7:44 pm

1 stop8h 59m

Chicago O'Hare Intl

Thu 9/11

8:05 am-4:27 pm

1 stop7h 22m

$173

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 9/11

11:25 am-7:44 pm

1 stop9h 19m

Chicago O'Hare Intl

Sun 9/14

8:05 am-4:27 pm

1 stop7h 22m

$173

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 9/25

11:40 am-7:44 pm

1 stop9h 04m

Chicago O'Hare Intl

Sun 9/28

8:05 am-4:27 pm

1 stop7h 22m

$173

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 9/17

11:35 am-9:58 pm

1 stop11h 23m

Chicago O'Hare Intl

Sat 9/20

5:17 pm-10:40 am

1 stop16h 23m

$175

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 10/18

12:38 pm-1:15 pm

1 stop25h 37m

Chicago O'Hare Intl

Sun 10/19

6:07 pm-10:37 am

1 stop15h 30m

$180

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 9/8

5:05 pm-10:52 am

2 stops18h 47m

Chicago O'Hare Intl

Sat 9/13

5:17 pm-10:40 am

1 stop16h 23m

$186

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 9/7

11:35 am-4:12 pm

1 stop29h 37m

Chicago O'Hare Intl

Mon 9/15

8:49 pm-10:40 am

1 stop12h 51m

$193

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 9/23

11:25 am-9:58 pm

1 stop11h 33m

Chicago O'Hare Intl

Mon 9/29

8:49 pm-10:40 am

1 stop12h 51m

$195

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 9/25

11:40 am-11:20 pm

2 stops12h 40m

Chicago O'Hare Intl

Mon 9/29

8:49 pm-10:40 am

1 stop12h 51m

$197

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 9/11

11:25 am-7:44 pm

1 stop9h 19m

$85

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 14 results
1
2

Best time to book a flight from Islip to Chicago

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

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

Currently, August is the cheapest month in which you can book a flight from Islip, New York to Chicago (average of $245). Flying from Islip, New York to Chicago in March is currently the most expensive (average of $321). 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.

How much does it cost to fly round-trip from Islip, New York to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated August 18, 2025.
Read reviews from past customers who have flown Southwest from Islip to Chicago. 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

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Islip to Chicago. 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 from for flights from Islip to Chicago?

    Most people fly from Islip Long Island (ISP) if they book a flight from Islip to Chicago. On average, Long Island has 0 outbound flights to 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 Islip, New York to Chicago?

    Departing from Islip, New York to Chicago will take you 8h 59m. The distance between Islip, New York and Chicago is about 770 mi.

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

    Cheapflights users have booked flights from Islip, New York to Chicago round-trip from $336. Southwest is currently priced 10% below the average price you’ll pay for this route.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Islip, New York to Chicago (average of $245). Flying from Islip, New York to Chicago in March is currently the most expensive (average of $321). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Islip to Chicago

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

Discover the top airline that operate flights from Islip to Chicago. 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$336Average$772FlexibilityNo cancel feeOn-time63%

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