$100 Cheap Flights from Islip (ISP) to Chicago (ORD)

View $100 flight on Sat, May 24, 2025Opens in a new window

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

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Find available prices by choosing your travel dates.

Cheap Flights from Islip to Chicago (ISP-ORD)

Prices were available within the past 7 days and start at $100 for one-way flights and $188 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, May 24 - Sat, May 31
ISP
Islip
ORD
Chicago
$188 Roundtrip, found 3 hours ago
$188
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, May 24 from Islip to Chicago, returning Sat, May 31, priced at $188 found 3 hours ago
Frontier Airlines
Sat, May 31 - Thu, Jun 5
ISP
Islip
ORD
Chicago
$198 Roundtrip, found 17 hours ago
$198
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sat, May 31 from Islip to Chicago, returning Thu, Jun 5, priced at $198 found 17 hours ago
Frontier Airlines
Thu, May 15 - Fri, May 16
ISP
Islip
ORD
Chicago
$208 Roundtrip, found 5 hours ago
$208
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Thu, May 15 from Islip to Chicago, returning Fri, May 16, priced at $208 found 5 hours ago
Frontier Airlines
Wed, May 21 - Thu, May 29
ISP
Islip
ORD
Chicago
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, May 21 from Islip to Chicago, returning Thu, May 29, priced at $218 found 1 day ago
Frontier Airlines
Tue, May 27 - Wed, Jun 4
ISP
Islip
ORD
Chicago
$221 Roundtrip, found 1 day ago
$221
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 27 from Islip to Chicago, returning Wed, Jun 4, priced at $221 found 1 day ago
Frontier Airlines
Thu, May 1 - Mon, May 5
ISP
Islip
ORD
Chicago
$228 Roundtrip, found 17 hours ago
$228
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, May 1 from Islip to Chicago, returning Mon, May 5, priced at $228 found 17 hours ago
Frontier Airlines
Mon, May 26 - Wed, Jun 4
ISP
Islip
ORD
Chicago
$230 Roundtrip, found 1 day ago
$230
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, May 26 from Islip to Chicago, returning Wed, Jun 4, priced at $230 found 1 day ago
Frontier Airlines
Tue, May 27 - Thu, Jun 5
ISP
Islip
ORD
Chicago
$231 Roundtrip, found 1 day ago
$231
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 27 from Islip to Chicago, returning Thu, Jun 5, priced at $231 found 1 day ago
JetBlue Airways
Sat, May 3 - Sat, May 10
ISP
Islip
ORD
Chicago
$240 Roundtrip, found 5 days ago
$240
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, May 3 from Islip to Chicago, returning Sat, May 10, priced at $240 found 5 days ago
Southwest Airlines
Tue, May 27 - Sat, May 31
ISP
Islip
ORD
Chicago
$266 Roundtrip, found 2 days ago
$266
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, May 27 from Islip to Chicago, returning Sat, May 31, priced at $266 found 2 days ago
Flights from Islip (ISP) to Chicago (ORD)
Origin airport
MacArthur
Destination airport
O'Hare Intl.
Airlines serving
Frontier Airlines, JetBlue Airways, Southwest Airlines
Roundtrip price
$188
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 May. 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 $100 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 O'Hare Intl. Airport (ORD) cost?
Discover the latest flight deals from ISP to ORD 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 ISP to ORD?
The cheapest flights from ISP to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from MacArthur Airport (ISP) to O'Hare Intl. Airport (ORD)?
There are no direct flights from Islip, NY (ISP-MacArthur) to O’Hare Intl. Airport (ORD). However, you’ll find other airports offering nonstop flights. Board your plane at John F. Kennedy Intl. Airport (JFK) and head straight to Chicago without a layover.
What is the cheapest airline that flies from ISP to ORD?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from ISP to ORD. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from MacArthur Airport (ISP) to O'Hare Intl. Airport (ORD)?
Nonstop flights from MacArthur Airport (ISP) to O’Hare Intl. Airport (ORD) 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 dates and select either “1 Stop” or “2+ Stops.”
What day of the week has the most flights from ISP to ORD?
Usually you’ll have the most choice when it comes to flights on a Friday. Tuesdays are often the quietest.* However, this can change depending on the airline, season 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 MacArthur Airport (ISP) to O'Hare Intl. Airport (ORD)?
Book a flight from MacArthur Airport (ISP) to O’Hare Intl. Airport (ORD) that takes off before 3 PM to reduce the risk of cancellations and delays. Departures after this hour are on average 22% more likely to be 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 O'Hare Intl. Airport (ORD) last-minute?
Last-minute bookings from ISP to ORD are usually more expensive. To lock in the lowest rates, start searching for flights well ahead of time. That being said, if you’re flexible with your travel dates, you may land a cheap ticket right before you leave.
Is it cheaper to book an ISP to ORD flight and hotel package?
Opting for an ISP to ORD flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip in one place. Choose from our wide range of accommodations 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 O'Hare Intl. Airport (ORD)?
It’s usually possible to reschedule or cancel your ISP to ORD flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline’s policies in your itinerary to see what changes are allowed and if any costs are involved. You’ll also find further details on our Customer Service portal.

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*Available to One Key members.