$60 Cheap Flights from Islip (ISP) to Chicago (ORD)

View $60 flight on Thu, Nov 20, 2025Opens in a new window

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

Cheap Flights from Islip to Chicago (ISP-ORD)

Prices were available within the past 7 days and start at $60 for one-way flights and $120 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, Jan 14 - Thu, Jan 22
ISP
Islip
ORD
Chicago
$120 Roundtrip, found 1 day ago
$120
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jan 14 from Islip to Chicago, returning Thu, Jan 22, priced at $120 found 1 day ago
Frontier Airlines
Thu, Nov 13 - Thu, Nov 20
ISP
Islip
ORD
Chicago
$130 Roundtrip, found 1 day ago
$130
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Islip to Chicago, returning Thu, Nov 20, priced at $130 found 1 day ago
Frontier Airlines
Fri, Nov 14 - Thu, Nov 20
ISP
Islip
ORD
Chicago
$153 Roundtrip, found 2 days ago
$153
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Nov 14 from Islip to Chicago, returning Thu, Nov 20, priced at $153 found 2 days ago
Frontier Airlines
Mon, Nov 10 - Thu, Nov 13
ISP
Islip
ORD
Chicago
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Nov 10 from Islip to Chicago, returning Thu, Nov 13, priced at $160 found 2 days ago
Frontier Airlines
Thu, Nov 13 - Thu, Nov 20
ISP
Islip
ORD
Chicago
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Islip to Chicago, returning Thu, Nov 20, priced at $170 found 1 day ago
Frontier Airlines
Thu, Nov 20 - Fri, Dec 5
ISP
Islip
ORD
Chicago
$173 Roundtrip, found 3 days ago
$173
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Nov 20 from Islip to Chicago, returning Fri, Dec 5, priced at $173 found 3 days ago
Frontier Airlines
Thu, Nov 13 - Thu, Nov 20
ISP
Islip
ORD
Chicago
$178 Roundtrip, found 1 day ago
$178
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Islip to Chicago, returning Thu, Nov 20, priced at $178 found 1 day ago
Frontier Airlines
Mon, Nov 10 - Thu, Nov 20
ISP
Islip
ORD
Chicago
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Nov 10 from Islip to Chicago, returning Thu, Nov 20, priced at $179 found 2 days ago
Southwest Airlines
Mon, Dec 8 - Tue, Dec 9
ISP
Islip
ORD
Chicago
$318 Roundtrip, found 23 hours ago
$318
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Mon, Dec 8 from Islip to Chicago, returning Tue, Dec 9, priced at $318 found 23 hours ago
JetBlue Airways
Tue, Jan 20 - Tue, Feb 3
ISP
Islip
ORD
Chicago
$338 Roundtrip, found 2 days ago
$338
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Jan 20 from Islip to Chicago, returning Tue, Feb 3, priced at $338 found 2 days ago

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

February is typically the cheapest month to fly

From $110 - $789 per traveler.

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $153
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $153

Frequently asked questions

How much does a flight from MacArthur Airport (ISP) to O'Hare Intl. Airport (ORD) cost?
Snag a cheap one-way flight from $60 or cheap return flight from $120 from MacArthur Airport (ISP) to O'Hare Intl. Airport (ORD) 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 O'Hare Intl. Airport (ORD)?
January is the cheapest month to fly from ISP to ORD. Planning your trip for the off-season is often the key to finding a great deal.
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 MacArthur Airport (ISP) to O'Hare Intl. Airport (ORD)?
To find the cheapest airline flying from ISP to ORD, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
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.

Travel information

Origin airport
MacArthur
Destination airport
O'Hare Intl.
Airlines serving
Frontier Airlines, JetBlue Airways, Southwest Airlines
Roundtrip price
$120
Distance
770 mi

Book with confidence

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 January. 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 $60 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.

 

Islip to Chicago Flights

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*Available to One Key members.