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$122+ Cheap flights from Islip (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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — CHI
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$227
(Trip.com)

One-way from

$122
(Kiwi.com)

Popular in

July

Cheapest in

April

Average price

$386
Provider with most accurate pricing for Islip Long Island-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Islip Long Island-Chicago (CHI) flights.
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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. 17% potential increase in price ($78 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 October 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 October 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/14. 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 10/294:58 pmISP - ORD
1 stop20h 28mFrontier
Sun 11/25:25 amORD - ISP
1 stop28h 12mFrontier
Deal found 10/14$208
This Trip.com deal was found by Cheapflights users on 10/12. 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.
Mon 10/279:49 amISP - ORD
2 stops15h 55mFrontier
Fri 10/315:25 amORD - ISP
1 stop28h 12mFrontier
Deal found 10/12$227
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 10/286:27 pmISP - ORD
1 stop22h 56mMultiple Airlines
Sat 11/11:13 pmORD - ISP
2 stops21h 47mMultiple Airlines
Deal found 10/13$247
This Trip.com deal was found by Cheapflights users on 10/12. 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.
Sat 10/254:58 pmISP - ORD
1 stop15h 16mMultiple Airlines
Wed 10/295:28 pmORD - ISP
1 stop23h 14mMultiple Airlines
Deal found 10/12$250
This Frontier deal was found by Cheapflights users on 10/13. 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 10/239:37 pmISP - ORD
1 stop10h 57mFrontier
Sun 10/268:14 amORD - ISP
1 stop11h 38mFrontier
Deal found 10/13$300
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 11/74:58 pmISP - ORD
2 stops19h 14mMultiple Airlines
Sun 11/95:25 amORD - ISP
1 stop28h 12mMultiple Airlines
Deal found 10/13$331
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 10/274:58 pmISP - ORD
1 stop24h 25mMultiple Airlines
Fri 10/315:28 pmORD - ISP
1 stop25h 37mMultiple Airlines
Deal found 10/12$332
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:55 amISP - ORD
1 stop9h 30mSouthwest
Wed 12/3111:55 amORD - ISP
2 stops9h 10mSouthwest
Deal found 10/13$339

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 October 14, 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

Wed 10/29

4:58 pm-12:26 pm

1 stop20h 28m

Chicago O'Hare Intl

Sun 11/2

5:25 am-10:37 am

1 stop28h 12m

$208

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 10/27

9:49 am-12:44 am

2 stops15h 55m

Chicago O'Hare Intl

Fri 10/31

5:25 am-10:37 am

1 stop28h 12m

$227

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 10/28

6:27 pm-4:23 pm

1 stop22h 56m

Chicago O'Hare Intl

Sat 11/1

1:13 pm-12:00 pm

2 stops21h 47m

$247

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 10/25

4:58 pm-7:14 am

1 stop15h 16m

Chicago O'Hare Intl

Wed 10/29

7:43 pm-5:42 pm

2 stops20h 59m

$273

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 10/27

4:58 pm-4:23 pm

1 stop24h 25m

Chicago O'Hare Intl

Fri 10/31

5:28 pm-8:05 pm

1 stop25h 37m

$332

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 12/22

6:55 am-3:25 pm

1 stop9h 30m

Chicago O'Hare Intl

Wed 12/31

11:55 am-10:05 pm

2 stops9h 10m

$339

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 11/7

9:39 am-5:10 pm

1 stop8h 31m

Chicago O'Hare Intl

Mon 11/10

5:15 am-7:06 pm

1 stop12h 51m

$344

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 3/16

8:19 pm-9:02 am

1 stop13h 43m

Chicago O'Hare Intl

Mon 3/23

10:12 am-7:11 pm

1 stop7h 59m

$381

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 12/22

9:09 pm-12:40 pm

1 stop16h 31m

Chicago O'Hare Intl

Wed 12/31

8:00 am-7:21 pm

1 stop10h 21m

$382

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 11/26

11:03 am-9:17 am

2 stops23h 14m

Chicago O'Hare Intl

Sun 11/30

7:09 pm-8:02 am

1 stop11h 53m

$527

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 19 results
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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Islip-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Islip-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Islip-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-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 to Chicago?

Currently, May is the cheapest month in which you can book a flight from Islip to Chicago (average of $55). Flying from Islip to Chicago in July is currently the most expensive (average of $126). 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 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 October 14, 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
4,238 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 to Chicago?

    Airlines like Frontier fly from Islip to Chicago in about 20h 28m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 770 mi.

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

    Cheapflights users have booked flights from Islip to Chicago round-trip from $306. This flight start at 17% lower than the current average price 3 months from now.

  • 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 to Chicago?

    Currently, May is the cheapest month in which you can book a flight from Islip to Chicago (average of $55). Flying from Islip to Chicago in July is currently the most expensive (average of $126). 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
Porter
Benton Harbor
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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$306Average$604FlexibilityNo cancel feeOn-time63%

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