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$144+ 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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$282
(FlightHub)

One-way from

$144
(Frontier)

Popular in

December

Cheapest in

April

Average price

$376
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. 22% potential increase in price ($93 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($29 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This FlightHub deal was found by Cheapflights users on 6/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/411:27 amISP - ORD
1 stop26h 30mFrontier
Mon 9/86:10 amORD - ISP
1 stop27h 27mFrontier
Deal found 6/11$282
This Southwest deal was found by Cheapflights users on 6/11. 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 9/46:25 amISP - ORD
1 stop6h 25mSouthwest
Mon 9/86:00 amORD - ISP
2 stops9h 30mSouthwest
Deal found 6/11$324
This Mytrip deal was found by Cheapflights users on 6/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/252:55 pmISP - ORD
2 stops23h 41mMultiple Airlines
Sun 6/2910:19 amORD - ISP
3 stops22h 45mMultiple Airlines
Deal found 6/9$599

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 12, 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

Thu 9/4

11:27 am-12:57 pm

1 stop26h 30m

Chicago O'Hare Intl

Mon 9/8

6:10 am-10:37 am

1 stop27h 27m

$282

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 9/4

6:25 am-11:50 am

1 stop6h 25m

Chicago O'Hare Intl

Mon 9/8

6:00 am-4:30 pm

2 stops9h 30m

$324

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 6/25

2:55 pm-1:36 pm

2 stops23h 41m

Chicago O'Hare Intl

Sun 6/29

10:19 am-10:04 am

3 stops22h 45m

$599

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 7/4

8:21 pm-8:07 am

1 stop12h 46m

$144

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 8/12

5:30 am-1:05 pm

1 stop8h 35m

$152

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 7/11

10:44 am-7:04 am

3 stops21h 20m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 12, 2025.
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $282. Another airline that can offer you cheap pricing is Southwest. Frontier is currently priced 11% 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, 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
Lansing
Benton Harbor
Porter
Hammond
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$336Average$892FlexibilityNo cancel feeOn-time63%

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