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$76+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — CHI
May 9 — May 161
Sat 5/9
Sat 5/16
1 adult, Economy
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1. Tell us where you want to go

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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 9, 2026.

This Expedia deal was found by Cheapflights users on 4/7. 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.
Fri 5/14:07 pm
ISP
-
ORD
1 stop24h 16m
Frontier
Sat 5/27:34 pm
ORD
-
ISP
1 stop23h 02m
Frontier
Deal found 4/7$181
This CheapOair deal was found by Cheapflights users on 4/7. 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.
Thu 4/238:31 pm
ISP
-
ORD
1 stop28h 56m
Frontier
Sat 4/258:00 am
ORD
-
ISP
1 stop24h 13m
Frontier
Deal found 4/7$201
This Frontier deal was found by Cheapflights users on 4/4. 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 4/198:31 pm
ISP
-
ORD
1 stop29h 38m
Frontier
Thu 4/232:05 pm
ORD
-
ISP
1 stop18h 08m
Frontier
Deal found 4/4$202
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 5/55:38 pm
ISP
-
ORD
1 stop30h 35m
Multiple Airlines
Tue 5/123:55 pm
ORD
-
ISP
2 stops18h 22m
Multiple Airlines
Deal found 4/5$206
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 4/244:07 pm
ISP
-
ORD
1 stop17h 58m
Multiple Airlines
Sun 4/266:00 am
ORD
-
ISP
1 stop26h 28m
Multiple Airlines
Deal found 4/4$227
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 5/55:38 pm
ISP
-
ORD
1 stop30h 35m
Frontier
Tue 5/123:55 pm
ORD
-
ISP
1 stop17h 10m
Frontier
Deal found 4/5$258
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 4/178:31 pm
ISP
-
ORD
1 stop15h 06m
Frontier
Sun 4/199:00 am
ORD
-
ISP
2 stops23h 13m
Frontier
Deal found 4/4$266
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 5/55:38 pm
ISP
-
ORD
1 stop29h 36m
Multiple Airlines
Thu 5/2110:49 am
ORD
-
ISP
1 stop22h 16m
Multiple Airlines
Deal found 4/8$275
This CheapOair deal was found by Cheapflights users on 4/7. 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.
Fri 4/105:45 am
ISP
-
ORD
1 stop19h 10m
Frontier
Mon 4/135:25 am
ORD
-
ISP
1 stop15h 13m
Frontier
Deal found 4/7$285

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 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$181
(Expedia)

One-way from

$76
(CheapOair)

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 9, 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

Tue 5/5

5:38 pm-11:13 pm

1 stop30h 35m

Chicago O'Hare Intl

Tue 5/12

3:55 pm-10:05 am

1 stop17h 10m

$258

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 5/5

5:38 pm-10:14 pm

1 stop29h 36m

Chicago O'Hare Intl

Thu 5/21

10:49 am-10:05 am

1 stop22h 16m

$275

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 5/5

6:30 am-4:05 pm

2 stops10h 35m

Chicago O'Hare Intl

Tue 5/12

11:55 am-10:10 pm

2 stops9h 15m

$345

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 4/29

6:30 am-4:05 pm

2 stops10h 35m

Chicago O'Hare Intl

Sat 5/2

6:00 am-4:00 pm

2 stops9h 00m

$365

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 5/15

12:30 pm-9:55 pm

2 stops10h 25m

Chicago O'Hare Intl

Mon 5/18

7:35 pm-11:55 am

2 stops15h 20m

$407

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 9/2

10:48 am-11:14 pm

1 stop13h 26m

Chicago O'Hare Intl

Tue 9/8

8:27 pm-11:20 am

2 stops13h 53m

$413

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 5/2

5:30 am-3:30 pm

2 stops11h 00m

Chicago O'Hare Intl

Tue 5/5

5:55 am-6:30 pm

2 stops11h 35m

$427

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 5/4

6:00 am-12:50 pm

2 stops7h 50m

Chicago O'Hare Intl

Thu 5/7

2:40 pm-11:30 pm

2 stops7h 50m

$429

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 4/24

8:31 pm-6:20 pm

1 stop22h 49m

Chicago O'Hare Intl

Mon 4/27

6:30 am-11:14 am

1 stop27h 44m

$442

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 5/1

6:00 am-3:30 pm

2 stops10h 30m

Chicago O'Hare Intl

Sat 5/2

12:15 pm-11:20 pm

2 stops10h 05m

$452

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/9

Showing 1-10 of 22 resultsSorted by cheapest first
1
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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 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

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

Currently, December is the cheapest month in which you can book a flight from Islip, New York to Chicago (average of $48). Flying from Islip, New York to Chicago in July is currently the most expensive (average of $119). 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 April 9, 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
4,338 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

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
4,338 reviews
Southwest
8.0
Very good
4,338 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

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 35m. The distance between Islip, New York and Chicago is about 770 mi. This flight may include one or multiple stops.

  • 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 $366. Southwest is currently priced 13% 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, December is the cheapest month in which you can book a flight from Islip, New York to Chicago (average of $48). Flying from Islip, New York to Chicago in July is currently the most expensive (average of $119). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$366Average$932FlexibilityNo cancel feeOn-time63%

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