HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$126+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — CHI
Aug 17 — Aug 241
Mon 8/17
Mon 8/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Islip to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 July 18, 2026.

This Expedia deal was found by Cheapflights users on 7/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:09 pm
ISP
-
ORD
1 stop19h 11m
Frontier
Thu 8/277:44 pm
ORD
-
ISP
1 stop13h 09m
Frontier
Deal found 7/15$252
This Frontier deal was found by Cheapflights users on 7/15. 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.
Sat 8/2910:57 am
ISP
-
ORD
1 stop13h 11m
Frontier
Sat 9/57:44 pm
ORD
-
ISP
1 stop13h 09m
Frontier
Deal found 7/15$253
This Frontier deal was found by Cheapflights users on 7/13. 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.
Wed 9/210:57 am
ISP
-
ORD
1 stop13h 11m
Frontier
Tue 9/87:44 pm
ORD
-
ISP
1 stop12h 49m
Frontier
Deal found 7/13$258
This Frontier deal was found by Cheapflights users on 7/14. 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.
Fri 8/2810:57 am
ISP
-
ORD
1 stop13h 11m
Frontier
Mon 8/316:05 am
ORD
-
ISP
1 stop11h 09m
Frontier
Deal found 7/14$260
This CheapOair deal was found by Cheapflights users on 7/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/234:13 pm
ISP
-
ORD
1 stop17h 08m
Frontier
Tue 10/274:44 pm
ORD
-
ISP
1 stop20h 49m
Frontier
Deal found 7/17$262
This Frontier deal was found by Cheapflights users on 7/13. 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.
Thu 8/2710:57 am
ISP
-
ORD
1 stop13h 11m
Frontier
Fri 8/286:05 am
ORD
-
ISP
1 stop11h 09m
Frontier
Deal found 7/13$263
This Frontier deal was found by Cheapflights users on 7/14. 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.
Fri 8/2810:57 am
ISP
-
ORD
1 stop13h 11m
Frontier
Sun 8/307:44 pm
ORD
-
ISP
1 stop13h 09m
Frontier
Deal found 7/14$268
This CheapOair deal was found by Cheapflights users on 7/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:13 pm
ISP
-
ORD
1 stop8h 42m
Frontier
Sun 10/44:49 pm
ORD
-
ISP
1 stop15h 44m
Frontier
Deal found 7/17$270
This Trip.com deal was found by Cheapflights users on 7/18. 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.
Wed 9/94:13 pm
ISP
-
ORD
1 stop8h 42m
Frontier
Fri 9/114:49 pm
ORD
-
ISP
1 stop15h 44m
Frontier
Deal found 7/18$276
This Frontier deal was found by Cheapflights users on 7/14. 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 9/310:57 am
ISP
-
ORD
1 stop13h 11m
Frontier
Mon 9/79:10 pm
ORD
-
ISP
1 stop11h 43m
Frontier
Deal found 7/14$278
This Trip.com deal was found by Cheapflights users on 7/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/810:57 am
ISP
-
ORD
1 stop13h 11m
Frontier
Fri 9/114:49 pm
ORD
-
ISP
1 stop15h 44m
Frontier
Deal found 7/15$283
This Frontier deal was found by Cheapflights users on 7/15. 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.
Wed 8/1910:57 am
ISP
-
ORD
1 stop13h 11m
Frontier
Sun 8/237:44 pm
ORD
-
ISP
1 stop13h 09m
Frontier
Deal found 7/15$286

Find 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 July 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$252
(Expedia)

One-way from

$126
(Frontier)

Popular in

March

Cheapest in

November

Average price

$448
Provider with most accurate pricing for Islip Long Island-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Islip Long Island-Chicago (CHI) flights.
Search Deals
From Islip Long Island to Chicago (CHI)
Search Deals
One-way flight from Islip Long Island to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 39% potential increase in price ($276 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 15% potential price decrease ($57 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 July 18, 2026.
Use the filters below to find and compare flights from Islip to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 8/28

10:57 am-11:08 pm

1 stop13h 11m

Chicago O'Hare Intl

Sun 8/30

7:44 pm-9:53 am

1 stop13h 09m

$268

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 9/3

10:57 am-11:08 pm

1 stop13h 11m

Chicago O'Hare Intl

Tue 9/8

7:44 pm-9:33 am

1 stop12h 49m

$297

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 8/20

10:57 am-11:08 pm

1 stop13h 11m

Chicago O'Hare Intl

Thu 8/27

7:44 pm-9:53 am

1 stop13h 09m

$300

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 8/15

10:43 am-11:10 pm

1 stop13h 27m

Chicago O'Hare Intl

Wed 8/19

5:59 pm-6:14 pm

1 stop23h 15m

$356

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 9/8

6:00 am-1:39 pm

1 stop8h 39m

Chicago O'Hare Intl

Sat 9/12

3:00 pm-11:22 pm

1 stop7h 22m

$379
Quickest round-trip

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 9/16

7:00 am-2:01 pm

1 stop8h 01m

Chicago O'Hare Intl

Sat 9/19

3:00 pm-11:22 pm

1 stop7h 22m

$399

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 9/12

7:00 am-2:01 pm

1 stop8h 01m

Chicago O'Hare Intl

Sat 9/19

3:00 pm-11:22 pm

1 stop7h 22m

$399

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 9/16

7:00 am-2:01 pm

1 stop8h 01m

Chicago O'Hare Intl

Fri 9/18

3:00 pm-11:22 pm

1 stop7h 22m

$437

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 9/22

7:00 am-2:01 pm

1 stop8h 01m

Chicago O'Hare Intl

Tue 9/29

3:00 pm-11:22 pm

1 stop7h 22m

$449

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 9/13

7:00 am-2:01 pm

1 stop8h 01m

Chicago O'Hare Intl

Thu 9/17

3:00 pm-11:22 pm

1 stop7h 22m

$471

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/17

Showing 1-10 of 23 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Islip to Chicago

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 Islip to Chicago in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
Trip.comPrice 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 Islip, New York-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Islip, New York-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Islip, New York-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Islip, New York-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub 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 Islip, New York-Chicago 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 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

No data available for this route at this time. Please check back soon.

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 July 18, 2026.
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
4,241 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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 0 airlines. 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 39m. The distance between Islip, New York and Chicago is about 770 mi. This flight may include one or multiple stops.

  • 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.

See more FAQs

Traveling to a place near Chicago?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.