Cheap Flights from Islip (ISP) to Chicago (PWK)

Popular airlines from MacArthur Airport (ISP) to Chicago, IL (PWK-Chicago Executive)

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $178
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $178
Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $180
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $180
Flights from Islip (ISP) to Chicago (PWK)
Origin airport
MacArthur
Destination airport
Chicago Executive
Distance
770 mi

Islip to Chicago Flights

The cheapest times to fly from Islip to Chicago

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 Islip to Chicago are during the month of . You can find some of the cheapest flights from Islip to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Islip to Chicago

Sunday is one of the best days to book for cheap flights from Islip to Chicago: 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 Islip to Chicago

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 Islip to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from 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 Islip to Chicago 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 Islip to Chicago 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 MacArthur Airport (ISP) to Chicago Executive Airport (PWK) cost?
Grab a cheap one-way flight or cheap return flight from MacArthur Airport (ISP) to Chicago Executive Airport (PWK) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from MacArthur Airport (ISP) to Chicago Executive Airport (PWK)?
Planning your trip for may help you find better deals, as it's the cheapest month for flights between ISP and PWK. You'll typically find the lowest fares during off-peak months.
What is the cheapest airline that flies from MacArthur Airport (ISP) to Chicago Executive Airport (PWK)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Select your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest ISP to PWK flight.
How many flights per day from MacArthur Airport (ISP) to Chicago Executive Airport (PWK)?
Nonstop flights from MacArthur Airport (ISP) to Chicago Executive Airport (PWK) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ISP to PWK?
You'll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from MacArthur Airport (ISP) to Chicago Executive Airport (PWK)?
To avoid potential delays on the MacArthur Airport (ISP) to Chicago Executive Airport (PWK) route, fly before 3 PM. Flights after this time have a 22% higher chance of being canceled.**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.
Is it cheaper to buy a plane ticket from MacArthur Airport (ISP) to Chicago Executive Airport (PWK) last-minute?
Waiting until just before your departure to book a flight from ISP to PWK generally means paying more. While you may find some last-minute offers, they're not always guaranteed. Be flexible with your travel plans to boost your chances of landing a bargain.
Is it cheaper to book an ISP to PWK flight and hotel package?
Securing an ISP to PWK flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels in one place. Select from our extensive range of stays and then add activities, flights 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 MacArthur Airport (ISP) to Chicago Executive Airport (PWK)?
Usually, it's possible to cancel or reschedule your ISP to PWK flight. However, for bookings made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more information on our Customer Service portal.

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*Available to One Key members.