$104 Cheap Flights from Chicago (ORD) to Islip (ISP)

View $104 flight on Thu, Aug 21, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to MacArthur Airport (ISP)

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Cheap Flights from Chicago to Islip (ORD-ISP)

Prices were available within the past 7 days and start at $104 for one-way flights and $201 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Mon, Sep 8 - Thu, Sep 11
ORD
Chicago
ISP
Islip
$201 Roundtrip, found 2 days ago
$201
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Sep 8 from Chicago to Islip, returning Thu, Sep 11, priced at $201 found 2 days ago
Frontier Airlines
Sun, Sep 7 - Thu, Sep 11
ORD
Chicago
ISP
Islip
$205 Roundtrip, found 2 days ago
$205
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Sep 7 from Chicago to Islip, returning Thu, Sep 11, priced at $205 found 2 days ago
Frontier Airlines
Thu, Aug 28 - Thu, Sep 4
ORD
Chicago
ISP
Islip
$211 Roundtrip, found 2 days ago
$211
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Aug 28 from Chicago to Islip, returning Thu, Sep 4, priced at $211 found 2 days ago
Frontier Airlines
Thu, Aug 21 - Fri, Aug 29
ORD
Chicago
ISP
Islip
$212 Roundtrip, found 6 hours ago
$212
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Thu, Aug 21 from Chicago to Islip, returning Fri, Aug 29, priced at $212 found 6 hours ago
Frontier Airlines
Sun, Sep 7 - Fri, Sep 12
ORD
Chicago
ISP
Islip
$221 Roundtrip, found 2 days ago
$221
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Sep 7 from Chicago to Islip, returning Fri, Sep 12, priced at $221 found 2 days ago
Frontier Airlines
Thu, Aug 28 - Sat, Aug 30
ORD
Chicago
ISP
Islip
$222 Roundtrip, found 2 days ago
$222
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Aug 28 from Chicago to Islip, returning Sat, Aug 30, priced at $222 found 2 days ago
Frontier Airlines
Thu, Aug 21 - Sun, Aug 24
ORD
Chicago
ISP
Islip
$226 Roundtrip, found 3 days ago
$226
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Aug 21 from Chicago to Islip, returning Sun, Aug 24, priced at $226 found 3 days ago
Frontier Airlines
Mon, Sep 8 - Wed, Sep 24
ORD
Chicago
ISP
Islip
$227 Roundtrip, found 18 hours ago
$227
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Mon, Sep 8 from Chicago to Islip, returning Wed, Sep 24, priced at $227 found 18 hours ago
Southwest Airlines
Wed, Aug 6 - Wed, Aug 13
ORD
Chicago
ISP
Islip
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Aug 6 from Chicago to Islip, returning Wed, Aug 13, priced at $237 found 3 days ago
JetBlue Airways
Tue, Jan 13 - Tue, Jan 27
ORD
Chicago
ISP
Islip
$433 Roundtrip, found 2 days ago
$433
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Jan 13 from Chicago to Islip, returning Tue, Jan 27, priced at $433 found 2 days ago

Find the cheapest month to fly from Chicago (ORD) to Islip (ISP)

February is typically the cheapest month to fly

From $110 - $685 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (ORD) to Islip (ISP)
Origin airport
O'Hare Intl.
Destination airport
MacArthur
Airlines serving
Frontier Airlines, JetBlue Airways, Southwest Airlines
Roundtrip price
$201
Distance
770 mi

Chicago to Islip Flights

The cheapest times to fly from Chicago to Islip

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Islip are during the month of September. You can find some of the cheapest flights from Chicago to Islip with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Islip

Sunday is one of the best days to book for cheap flights from Chicago to Islip: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Islip

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Islip in 2025. You can also book with separate airlines for your outbound and return journeys, from $104 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Islip flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Islip airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to MacArthur Airport (ISP) cost?
Discover the latest flight deals from ORD to ISP by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ORD to ISP?
The cheapest flights from ORD to ISP are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to ISP?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from ORD to ISP. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to MacArthur Airport (ISP)?
Direct flights from O'Hare Intl. Airport (ORD) to MacArthur Airport (ISP) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel details and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to ISP?
Generally you'll have the most choice when it comes to flights on a Friday. Tuesdays tend to be the quietest.* But this can vary depending on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to MacArthur Airport (ISP)?
Choose a flight from O'Hare Intl. Airport (ORD) to MacArthur Airport (ISP) that takes off before 3 PM to reduce the likelihood of delays. Departures after this time have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Islip from O'Hare Intl. Airport (ORD)?
You can arrive at one of these Islip airports following your direct flight from O'Hare Intl. Airport (ORD):

  • LaGuardia Airport (LGA)
  • John F. Kennedy Intl. Airport (JFK)
  • Westchester County Airport (HPN)

Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to MacArthur Airport (ISP) last-minute?
Booking your flight from ORD to ISP shortly before your journey is generally more expensive. However, if there's some wiggle room with your travel dates and times, you could land a cheap last-minute fare.
Is it cheaper to book an ORD to ISP flight and hotel package?
You can save money by booking an ORD to ISP flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one convenient place. After selecting your preferred accommodations and flights, you can add extras like tours, activities and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to MacArthur Airport (ISP)?
You can usually reschedule or cancel your ORD to ISP flight. However, for bookings made more than 24 hours ago, additional charges may apply. Check your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more details on our Customer Service portal.

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*Available to One Key members.