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$96+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — CHI
May 17 — May 241
Sun 5/17
Sun 5/24
1 adult, Economy
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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 April 17, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:02 pm
ISP
-
ORD
1 stop30h 11m
Frontier
Thu 5/285:11 pm
ORD
-
ISP
1 stop15h 54m
Frontier
Deal found 4/13$203
This Trip.com deal was found by Cheapflights users on 4/15. 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.
Thu 4/304:07 pm
ISP
-
ORD
1 stop22h 08m
Frontier
Mon 5/46:00 am
ORD
-
ISP
1 stop28h 00m
Frontier
Deal found 4/15$218
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Thu 5/1411:12 am
ISP
-
ORD
1 stop12h 02m
Multiple Airlines
Tue 5/193:55 pm
ORD
-
ISP
1 stop17h 10m
Multiple Airlines
Deal found 4/14$239
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Wed 5/1311:00 am
ISP
-
ORD
1 stop12h 14m
Multiple Airlines
Mon 5/186:55 am
ORD
-
ISP
2 stops27h 05m
Multiple Airlines
Deal found 4/14$241
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:31 pm
ISP
-
ORD
1 stop22h 49m
Multiple Airlines
Mon 5/42:10 pm
ORD
-
ISP
2 stops19h 50m
Multiple Airlines
Deal found 4/15$245
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Fri 5/2911:00 am
ISP
-
ORD
1 stop13h 13m
Frontier
Mon 6/11:50 pm
ORD
-
ISP
2 stops26h 27m
Frontier
Deal found 4/14$253
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Fri 5/18:31 pm
ISP
-
ORD
1 stop22h 49m
Multiple Airlines
Tue 5/57:15 am
ORD
-
ISP
2 stops25h 50m
Multiple Airlines
Deal found 4/16$254
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Fri 5/2911:00 am
ISP
-
ORD
1 stop13h 13m
Multiple Airlines
Mon 6/18:30 am
ORD
-
ISP
1 stop8h 28m
Multiple Airlines
Deal found 4/14$259
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2911:00 am
ISP
-
ORD
1 stop13h 13m
Frontier
Fri 6/55:11 pm
ORD
-
ISP
1 stop15h 54m
Frontier
Deal found 4/13$268
This Trip.com deal was found by Cheapflights users on 4/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1411:12 am
ISP
-
ORD
1 stop13h 01m
Frontier
Mon 5/186:55 am
ORD
-
ISP
2 stops27h 05m
Frontier
Deal found 4/14$269
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1311:00 am
ISP
-
ORD
1 stop12h 14m
Multiple Airlines
Wed 5/2010:49 am
ORD
-
ISP
1 stop22h 38m
Multiple Airlines
Deal found 4/15$271

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 April 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$203
(Kiwi.com)

One-way from

$96
(Frontier)

Popular in

March

Cheapest in

May

Average price

$421
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. 37% potential increase in price ($253 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 April 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 April 17, 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

Mon 6/1

2:28 pm-7:51 pm

2 stops30h 23m

Chicago O'Hare Intl

Fri 6/5

5:11 pm-10:05 am

1 stop15h 54m

$294

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 4/27

8:31 pm-6:20 pm

1 stop22h 49m

Chicago O'Hare Intl

Fri 5/1

5:50 am-7:36 pm

2 stops12h 46m

$324

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 5/1

4:07 pm-11:33 am

2 stops20h 26m

Chicago O'Hare Intl

Sat 5/2

4:50 pm-9:13 am

1 stop15h 23m

$335

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 5/13

12:30 pm-9:55 pm

2 stops10h 25m

Chicago O'Hare Intl

Wed 5/20

11:55 am-10:10 pm

2 stops9h 15m

$345

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 5/26

6:55 am-6:25 pm

1 stop12h 30m

Chicago O'Hare Intl

Thu 5/28

3:05 pm-10:30 pm

1 stop6h 25m

$360

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 5/5

6:30 am-4:05 pm

2 stops10h 35m

Chicago O'Hare Intl

Wed 5/6

11:55 am-10:10 pm

2 stops9h 15m

$365
Quickest round-trip

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 5/18

6:00 am-12:50 pm

2 stops7h 50m

Chicago O'Hare Intl

Sat 5/23

12:15 pm-10:40 pm

1 stop9h 25m

$380

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 5/30

6:00 am-3:30 pm

2 stops10h 30m

Chicago O'Hare Intl

Sun 5/31

1:35 pm-11:45 pm

1 stop9h 10m

$396
Cheapest one-way

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 5/30

11:00 am-11:13 pm

1 stop13h 13m

$97

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 5/18

11:00 am-11:13 pm

1 stop13h 13m

$117

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 19 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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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 April 17, 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
4,328 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,328 reviews
Southwest
8.0
Very good
4,328 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 10h 25m. 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 $387. Southwest is currently priced 8% 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.

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
Hammond
Porter

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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 April 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$387Average$1,046FlexibilityNo cancel feeOn-time63%

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