C$104 Cheap Flights from Chicago (CHIA) to Islip (ISP)

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Find the cheapest month or even day of the year to fly to Islip

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Find the cheapest month to fly from Chicago to Islip

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Islip flights are currently cheapest in May.

Chicago to Islip: Flight information

The things to know before you go.
Cheapest flight foundC$104
Cheapest month to flyMay

Finding cheap flights from Chicago to Islip: Frequently asked questions

The best price we found for a return flight from Chicago to Islip is C$348. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Chicago to Islip. But we found flights with one stop from C$348.
As of April 2026, there are no flights flying from Chicago to Islip.
The cheapest month to fly from Chicago to Islip is usually April.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Islip Airport on Thursday, April 16, 2026.
No airlines currently offer direct flights between Chicago and Islip Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Islip but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Islip is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Islip is Spirit Airlines .

Travelling from Chicago to Long Island MacArthur Airport (ISP): what you need to know

  • Begin your trip planning by checking out the most convenient departure point for your flight from Chicago to Long Island MacArthur Airport (ISP). Explore the options for taking off from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW), two of the city's main airports.

  • The timezone in Islip is UTC-4, which is 1 hour ahead of Chicago. Long Island MacArthur Airport is located in Islip.

  • Your flight from Chicago to ISP won't wait if you're late, so be at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're travelling internationally.

  • Peak months like August or vacation times such as Christmas and New Year will mean longer queues at check-in and security. Play it safe and head to the terminal even earlier. Arriving two hours before a domestic flight and up four hours ahead of international flights is wise.

Airports in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

About Long Island MacArthur Airport (ISP)

Getting from Long Island MacArthur Airport (ISP) to central Islip

  • Long Island MacArthur Airport is approximately 16 kilometres from central Islip. With your own car rental or if you take a cab, the drive is around 17 minutes.

  • It'll take around 1 hour and 11 minutes to get there using public transport.

How to find the cheapest flights from Chicago to Long Island MacArthur Airport (ISP)

  • C$104 is the lowest price we've seen for a one-way ticket from Chicago to Long Island MacArthur Airport. Return flights start from C$348. Prices are subject to change based on availability and may vary at the time of booking.

  • Don't leave everything to the last minute. You're more likely to find flight tickets from Chicago to ISP if you book in advance. Airlines often have some excellent early bird discounts.

  • If you're flexible with your travel plans, make the most of the 'Whole month' tool. It'll give you the cheapest price across each month when searching for your ticket from Chicago to Long Island MacArthur Airport.

  • Locking in a cheap ticket from Chicago to ISP is easy with Price Alerts. All you need to do is set up one of these automatic alerts and we'll get in touch when the price has fallen.

  • Use the filters to tailor your flights from Chicago to Long Island MacArthur Airport. Pick your ideal departure and arrival times, airlines and number of stops. You can also sort your results by 'Cheapest' to get the best deals.

The best time to fly from Chicago to Long Island MacArthur Airport (ISP)

  • August is the most popular month for flights from Chicago to Long Island MacArthur Airport. To escape the crowds, plan your trip to Islip in May when it's quieter.

  • Lock in your flight from Chicago to ISP for July if you're eager to head to the city during its warmest month. You can expect temperatures in Islip to range from 19ºC to 29ºC.

  • If you want to travel in cooler conditions, look for a cheap flight from Chicago to Long Island MacArthur Airport in January when temperatures average between -4ºC and 8ºC.

More about Islip

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.