£272 Cheap Flights from Islip (ISP) to Chicago (ORD)

View £272 flight on Thu, 28 Aug 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at £272 for one-way flights and £608 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Cape Air
Fri, 22 Aug - Sun, 24 Aug
ISP
Islip
ORD
Chicago
£608 Return, found 4 days ago
£608
Return
found 4 days ago
Select Cape Air flight, departing Fri, 22 Aug from Islip to Chicago, returning Sun, 24 Aug, priced at £608 found 4 days ago

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

February is typically the cheapest month to fly

From £83 - £607 per traveller.

Graph displaying average flight prices per month

Flight from Islip to Chicago route information
Origin airport
MacArthur
Destination airport
O'Hare Intl.
Return price
£607
Distance
1233 km

Compare flights from Islip to Chicago easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Islip to Chicago. Operating between them flights per day, 12 airlines cover the route. And fly direct, getting you to O'Hare Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from MacArthur to O'Hare Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from MacArthur (ISP) to O'Hare Intl. (ORD)

The easiest way to view the best deals on flights from Islip to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from MacArthur to O'Hare Intl. start at just £608 and range up to £608.  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Islip and Chicago
  • booking your flight during August, the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Islip to Chicago flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from MacArthur to O'Hare Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Frequently asked questions

How much is a flight from MacArthur Airport to O'Hare Airport?
Based on fares quoted within the last 7 days on Expedia for flights departing within the next year, round-trip journeys from ISP to ORD start from £608. Book ASAP to secure the best price for your next big adventure. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from MacArthur Airport to O'Hare Airport?
This can vary between airlines, as each has its own set of terms and conditions. Head to the Customer Service Portal, where there are easy-to-follow instructions on how to cancel your flight online.
How do I find cheap flights from ISP to O'Hare Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for MacArthur Airport to ORD flights, you'll see a "no change fees" filter for you to select.
How far is the flight from MacArthur Airport (ISP) to O'Hare Airport?
A flight distance of just 1,250 kilometres separates Ronkonkoma and Chicago. Once you're in the air, you won't get a chance to do much more than read the magazine in your seat pocket.
Which airlines fly direct from MacArthur Airport to O'Hare Intl. Airport (ORD)?
If you want to fly straight from ISP to ORD, you'll have to book a flight with one or more stops. Unfortunately, there are no airlines that fly directly between these airports.
Are MacArthur Airport to ORD flight tickets cheaper when they're purchased at the last minute?
Last-minute planners can sometimes score a bargain, with some of the cheapest fares from ISP to ORD emerging a few weeks prior to the departure date. If you'd rather book ahead, Expedia compares and updates all the best flight deals frequently — as early as 12 months in advance in some cases. It depends on the carrier though, as not every airline releases prices that far in advance.

Explore a world of travel with Expedia

Islip Airports

New York

LaGuardia to Chicago
£104.70
John F. Kennedy Intl. to Chicago
£104.70
*Available to Expedia members.