$96 Cheap Flights from Chicago (ORD) to Islip (ISP)

View $96 flight on Thu, Apr 16, 2026Opens in a new window

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

Cheap Flights from Chicago to Islip (ORD-ISP)

Prices were available within the past 7 days and start at $96 for one-way flights and $160 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Apr 16 - Sun, Apr 19
ORD
Chicago
ISP
Islip
$160 Roundtrip, found 10 hours ago
$160
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Chicago to Islip, returning Sun, Apr 19, priced at $160 found 10 hours ago
Frontier Airlines
Sun, Apr 26 - Sun, May 3
ORD
Chicago
ISP
Islip
$172 Roundtrip, found 1 day ago
$172
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Apr 26 from Chicago to Islip, returning Sun, May 3, priced at $172 found 1 day ago
Frontier Airlines
Thu, Apr 30 - Wed, May 6
ORD
Chicago
ISP
Islip
$180 Roundtrip, found 13 hours ago
$180
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Chicago to Islip, returning Wed, May 6, priced at $180 found 13 hours ago
Frontier Airlines
Thu, Apr 16 - Sun, Apr 19
ORD
Chicago
ISP
Islip
$201 Roundtrip, found 10 hours ago
$201
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Chicago to Islip, returning Sun, Apr 19, priced at $201 found 10 hours ago
Frontier Airlines
Thu, Apr 23 - Fri, May 1
ORD
Chicago
ISP
Islip
$213 Roundtrip, found 4 days ago
$213
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Apr 23 from Chicago to Islip, returning Fri, May 1, priced at $213 found 4 days ago
Frontier Airlines
Sun, May 3 - Sat, May 9
ORD
Chicago
ISP
Islip
$218 Roundtrip, found 14 hours ago
$218
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sun, May 3 from Chicago to Islip, returning Sat, May 9, priced at $218 found 14 hours ago
Frontier Airlines
Sat, Apr 4 - Tue, Apr 7
ORD
Chicago
ISP
Islip
$226 Roundtrip, found 15 hours ago
$226
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sat, Apr 4 from Chicago to Islip, returning Tue, Apr 7, priced at $226 found 15 hours ago
Frontier Airlines
Thu, Apr 30 - Wed, May 6
ORD
Chicago
ISP
Islip
$231 Roundtrip, found 13 hours ago
$231
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Chicago to Islip, returning Wed, May 6, priced at $231 found 13 hours ago
Southwest Airlines
Tue, May 12 - Thu, May 14
ORD
Chicago
ISP
Islip
$273 Roundtrip, found 12 hours ago
$273
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Tue, May 12 from Chicago to Islip, returning Thu, May 14, priced at $273 found 12 hours ago
JetBlue Airways
Fri, Mar 27 - Thu, Apr 2
ORD
Chicago
ISP
Islip
$1,779 Roundtrip, found 1 day ago
$1,779
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Mar 27 from Chicago to Islip, returning Thu, Apr 2, priced at $1,779 found 1 day ago

Alternative airports near Islip

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to MacArthur ISP. Cheapest and Closest option available. Average driving time to city center is 14 minutes. Flights from $534
ISP
MacArthur
CheapestClosest
Average driving time to city center14 min
Flights from $534

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

February is typically the cheapest month to fly

From $110 - $730 per traveler.

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur) cost?
You can find cheap one-way flights from $96 and cheap return flights from $160 Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur) with Expedia. Roundtrip flights usually range from $340 to $2164. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur)?
The cheapest month to fly from ORD to ISP is April when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur)?
Enter ORD to ISP and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur)?
Frontier Airlines is one of the cheapest airlines offering connecting flights from O'Hare Intl. (ORD) to MacArthur (ISP), with round-trip tickets starting from around $360. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur)?
The earliest flight from Chicago, IL (ORD) to Islip, NY (ISP) typically leaves at around 5:00 AM, operated by American Airlines. This is a seasonal service active in October, and an early departure can help you maximize your time in Islip. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur)?
a Wednesday typically has the most flights from O'Hare Intl. (ORD) to MacArthur (ISP), with approximately 18 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include United and American Airlines.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur)?
The most popular departure times for flights from Chicago (ORD) to Islip (ISP) are in the early morning, from 6am to 9am. About 62% of passengers prefer this time window. Many major carriers, including Southwest Airlines and United Airlines, operate flights during this time. This early schedule is great for travelers looking to start their day in Islip.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur)?
Flying from ORD to ISP with a connection usually takes about 8 hours, traveling roughly 771 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur)?
Select the "Business class" and "First class" filters when looking for ORD to ISP flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Islip from O'Hare Intl. (ORD)?
From O'Hare Intl. (ORD), you can fly into MacArthur (ISP) to reach Islip. Some flights may connect through major hubs like Liberty Intl. (EWR), Orlando Intl. (MCO), LaGuardia (LGA) before reaching Islip. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur) flight and hotel package?
Securing a Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Islip, NY (ISP-MacArthur) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
MacArthur
Airlines serving
Frontier Airlines, JetBlue Airways, Southwest Airlines
Roundtrip price
$160
Distance
770 mi

Book with confidence

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 April. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $96 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.

 

Chicago to Islip Flights

*Flight schedules are subject to change.

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*Available to One Key members.