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$134+ 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 7/18. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — CHI
Jul 4 — Jul 111
Sat 7/4
Sat 7/11
1 adult, Economy
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Find cheap flights from Islip to Chicago with Cheapflights

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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 June 4, 2026.

This Booking.com deal was found by Cheapflights users on 6/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/210:48 am
ISP
-
ORD
1 stop23h 33m
Frontier
Tue 7/75:13 pm
ORD
-
ISP
1 stop15h 40m
Frontier
Deal found 6/2$301
This Booking.com deal was found by Cheapflights users on 6/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/210:48 am
ISP
-
ORD
1 stop23h 33m
Frontier
Thu 7/95:13 pm
ORD
-
ISP
1 stop15h 40m
Frontier
Deal found 6/2$307
This Travelocity deal was found by Cheapflights users on 6/3. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2210:57 am
ISP
-
ORD
1 stop13h 13m
Frontier
Tue 7/285:13 pm
ORD
-
ISP
1 stop15h 40m
Frontier
Deal found 6/3$308
This Frontier deal was found by Cheapflights users on 6/2. 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 9/104:13 pm
ISP
-
ORD
1 stop8h 42m
Frontier
Sun 9/139:26 am
ORD
-
ISP
1 stop23h 07m
Frontier
Deal found 6/2$309
This Kiwi.com deal was found by Cheapflights users on 6/2. 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.
Thu 8/2710:48 am
ISP
-
ORD
1 stop13h 26m
Multiple Airlines
Mon 8/315:30 pm
ORD
-
ISP
2 stops22h 17m
Multiple Airlines
Deal found 6/2$324
This Kiwi.com deal was found by Cheapflights users on 6/2. 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.
Thu 8/2710:48 am
ISP
-
ORD
1 stop13h 26m
Multiple Airlines
Tue 9/15:30 pm
ORD
-
ISP
2 stops16h 47m
Multiple Airlines
Deal found 6/2$335
This Expedia deal was found by Cheapflights users on 6/2. 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.
Tue 6/234:41 pm
ISP
-
ORD
1 stop7h 38m
Frontier
Fri 6/264:59 pm
ORD
-
ISP
1 stop26h 58m
Frontier
Deal found 6/2$339
This Expedia deal was found by Cheapflights users on 6/1. 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.
Wed 7/19:52 pm
ISP
-
ORD
1 stop26h 27m
Frontier
Tue 7/75:13 pm
ORD
-
ISP
1 stop15h 40m
Frontier
Deal found 6/1$349
This Kiwi.com deal was found by Cheapflights users on 5/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:57 am
ISP
-
ORD
2 stops36h 17m
Multiple Airlines
Tue 9/15:30 pm
ORD
-
ISP
1 stop15h 33m
Multiple Airlines
Deal found 5/30$352
This Booking.com deal was found by Cheapflights users on 6/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/289:52 pm
ISP
-
ORD
1 stop12h 29m
Frontier
Thu 7/24:59 pm
ORD
-
ISP
1 stop16h 04m
Frontier
Deal found 6/1$357

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 June 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$301
(Booking.com)

One-way from

$134
(Frontier)

Popular in

March

Cheapest in

May

Average price

$419
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 ($279 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 June 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 June 4, 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

Wed 7/1

9:52 pm-11:19 pm

1 stop26h 27m

Chicago O'Hare Intl

Tue 7/7

5:13 pm-9:53 am

1 stop15h 40m

$349

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 8/26

11:57 am-11:14 pm

2 stops36h 17m

Chicago O'Hare Intl

Tue 9/1

5:30 pm-10:03 am

1 stop15h 33m

$352

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 6/28

9:52 pm-9:21 am

1 stop12h 29m

Chicago O'Hare Intl

Thu 7/2

4:59 pm-10:03 am

1 stop16h 04m

$357
Quickest round-trip

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 8/26

6:00 am-1:39 pm

1 stop8h 39m

Chicago O'Hare Intl

Tue 9/1

2:35 pm-10:56 pm

1 stop7h 21m

$363

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 7/3

10:48 am-11:19 pm

1 stop13h 31m

Chicago O'Hare Intl

Fri 7/10

10:16 am-9:53 am

1 stop22h 37m

$381

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 8/19

10:48 am-11:14 pm

1 stop13h 26m

Chicago O'Hare Intl

Sun 8/23

5:30 pm-10:03 am

1 stop15h 33m

$411

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 8/25

6:00 am-1:39 pm

1 stop8h 39m

Chicago O'Hare Intl

Thu 8/27

2:35 pm-10:56 pm

1 stop7h 21m

$418

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 8/26

10:48 am-11:14 pm

1 stop13h 26m

Chicago O'Hare Intl

Tue 9/1

5:30 pm-10:03 am

1 stop15h 33m

$468

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 7/3

2:28 pm-11:19 pm

2 stops33h 51m

Chicago O'Hare Intl

Fri 7/10

5:13 pm-9:53 am

1 stop15h 40m

$473

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 7/17

10:57 am-11:10 pm

1 stop13h 13m

Chicago O'Hare Intl

Mon 7/20

5:13 pm-4:47 pm

2 stops22h 34m

$480

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/3

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 June.
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

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 June 4, 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
4,256 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!
Southwest
8.0
Very good
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

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
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