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$97+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — CHI
Apr 27 — May 41
Sun 4/27
Sun 5/4
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 April 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$181
(CheapOair)

One-way from

$97
(CheapOair)

Popular in

December

Cheapest in

April

Average price

$81
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. 20% potential increase in price ($86 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 22, 2025.

This CheapOair deal was found by Cheapflights users on 4/21. 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 5/77:15 pmISP - ORD
1 stop29h 17mFrontier
Sat 5/104:15 pmORD - ISP
1 stop16h 57mFrontier
Deal found 4/21$181
This JetBlue deal was found by Cheapflights users on 4/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/316:00 amISP - ORD
1 stop5h 08mJetBlue
Sat 6/710:50 amORD - ISP
1 stop9h 38mJetBlue
Deal found 4/21$313
This Trip.com deal was found by Cheapflights users on 4/21. 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.
Sun 5/1811:02 amISP - ORD
1 stop14h 03mMultiple Airlines
Tue 5/205:05 amORD - ISP
1 stop13h 12mMultiple Airlines
Deal found 4/21$314
This Southwest deal was found by Cheapflights users on 4/21. 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.
Thu 8/76:00 amISP - ORD
1 stop7h 45mSouthwest
Sat 8/161:30 pmORD - ISP
1 stop7h 10mSouthwest
Deal found 4/21$324

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 22, 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 5/7

7:15 pm-11:32 pm

1 stop29h 17m

Chicago O'Hare Intl

Sat 5/10

4:15 pm-10:12 am

1 stop16h 57m

$181

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 5/31

6:00 am-10:08 am

1 stop5h 08m

Chicago O'Hare Intl

Sat 6/7

10:50 am-9:28 pm

1 stop9h 38m

$313

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 5/18

11:02 am-12:05 am

1 stop14h 03m

Chicago O'Hare Intl

Tue 5/20

5:05 am-7:17 pm

1 stop13h 12m

$314

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 8/7

6:00 am-12:45 pm

1 stop7h 45m

Chicago O'Hare Intl

Sat 8/16

1:30 pm-9:40 pm

1 stop7h 10m

$324

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 4/30

6:51 pm-11:32 pm

1 stop29h 41m

$97

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 5/10

6:00 am-10:08 am

1 stop5h 08m

$142

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 8/16

5:40 am-11:50 am

1 stop7h 10m

$152

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 5/12

10:44 am-8:50 am

3 stops23h 06m

$218

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

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*2 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, 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 eDreams the most. eDreams 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, August is the cheapest month in which you can book a flight from Islip, New York to Chicago (average of $245). Flying from Islip, New York to Chicago in March is currently the most expensive (average of $321). 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 22, 2025.
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,923 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,283 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

  • What are the cheapest airlines flying from Islip, New York to Chicago round-trip?

    Cheapflights users have booked flights from Islip, New York to Chicago round-trip from $181. Other airlines that can offer you cheap pricing are JetBlue, from $313, and Southwest, from $324. Frontier is currently priced 44% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Islip, New York to Chicago one-way?

    One-way options have recently been found by users for as low as $97 on Frontier. Other airlines that offer cheap prices include JetBlue from $142 and Southwest from $152 one-way.

  • 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, August is the cheapest month in which you can book a flight from Islip, New York to Chicago (average of $245). Flying from Islip, New York to Chicago in March is currently the most expensive (average of $321). 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 Islip?

Book flights to Islip if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$296Average$366FlexibilityNo cancel feeOn-time63%

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