$86 Flights from Chicago (CHIA) to Islip (ISP)

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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 March.

Chicago to Islip: Flight information

The things to know before you go.
Cheapest flight found$86
Cheapest month to flyMarch

Finding cheap flights from Chicago to Islip: Frequently asked questions

The best price we found for a round-trip flight from Chicago to Islip is $179. 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 $179.
There are no flights flying from Chicago to Islip, as of February 2026.
The cheapest month to fly from Chicago to Islip is usually March.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Islip Airport on Sunday, March 1, 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 Frontier Airlines.

Flying from Chicago to Long Island MacArthur Airport (ISP): What you need to know

  • Start your journey at one of Chicago's main airports, O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Check out your options for booking a flight from Chicago to Long Island MacArthur Airport (ISP) departing from either of these.

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

  • Get to the airport on time so you don't miss your flight from Chicago to ISP. Be there at least two hours ahead for international flights and an hour early for domestic departures to prevent a last-minute sprint to your gate.

  • With more travelers during peak seasons, it's wise to get to your terminal even earlier. Two hours for domestic flights and up to four for international trips will help you stay ahead of the crowds.

Airports in Chicago

O'Hare International Airport (ORD)

  • ORD is about 25 miles from central Chicago. If you're driving, catching a cab or ride-sharing from the center, it'll take you 35 minutes or so to get there, depending on the traffic. If you're taking public transport, expect the trip time to be around 55 minutes.

  • Searching for a comfortable hotel close to O'Hare International Airport? If you're catching an early flight from Chicago to Long Island MacArthur Airport, these accommodation options will have you sleeping just around the corner from the terminal:

  • 74.85% of flights that take off from O'Hare International Airport reach their destination on time.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Using public transport, you can travel from central Chicago to MDW in about 45 minutes. The airport is roughly 12 miles away, and getting there by car takes approximately 20 minutes.

  • Flying off with the first light? You might like to check in to one of these accommodation options near Chicago Midway International Airport the day before your Chicago to ISP flight:

  • Chicago Midway International Airport has an on-time performance of 77.88%. This figure sheds light on how frequently flights departing from this airport land at their destination on time.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • From the center of Chicago, RFD is around 85 miles away. It takes roughly 1 hour 25 minutes to reach the airport by car and 4 hours 15 minutes or so if you take public transport.

  • Rest a little longer, move a little slower, and still make your Chicago to Long Island MacArthur Airport flight without having to rush. These accommodation options near Chicago Rockford International Airport make departure day effortless if you're jetting off early:

  • Airports have an on-time performance rating that measures how often flights get to their destinations when they should. At RFD, that figure is 76.19%.

  • The address of Chicago Rockford International Airport is 2 Airport Cir.

About Long Island MacArthur Airport (ISP)

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

  • Central Islip is around 7 miles from Long Island MacArthur Airport. Travel times by car rental or cab will vary depending on traffic conditions, so do some research before your trip.

  • It takes roughly 1 hour 10 minutes if you're using public transport.

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

  • $86 is the best price for a one-way ticket from Chicago to Long Island MacArthur Airport. A return flight starts from $179. These prices may change based on availability.

  • Don't leave things to the last minute. You're more likely to walk away with cheap flights from Chicago to ISP if you book early. Airlines often offer some amazing early bird rates.

  • If you're flexible with your travel plans, use the 'Whole month' search tool. It'll show you the cheapest price across every month when searching for your Chicago to Long Island MacArthur Airport ticket.

  • Be the first to know about deals for plane tickets from Chicago to ISP by creating a Price Alert. We'll send you an email or notification through the app when prices go down.

  • Filters make it easier to scoop up a deal on your flight from Chicago to Long Island MacArthur Airport. Pick the flight times, carriers and stops that line up with your plans. Then sort the results by 'Cheapest' to bring up the lowest fares right away.

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

  • May is the quietest month for flights from Chicago to Long Island MacArthur Airport (ISP), while August is the busiest. Choose the best time to go to Islip based on whether you prefer a laid-back vibe or a lively atmosphere.

  • When booking your Chicago to ISP plane ticket, consider the kind of weather you prefer. July is the warmest month in Islip, with temperatures ranging from 66ºF to 84ºF.

  • For cooler conditions, look for a cheap ticket from Chicago to Long Island MacArthur Airport in January when temperatures are between 25ºF and 46ºF.

More about Islip

Explore more of the United States

  • Islip has its own special appeal, but there are so many other parts of the United States just waiting to be discovered. About 120 miles south-west of Islip, a trip to Philadelphia will keep your itinerary packed. Start with leading attractions like Independence Hall, Liberty Bell and Philadelphia Museum of Art.

  • Around 150 miles north-east of Islip, Boston is another favorite stop in the United States. Experience the best of this destination with a visit to Museum of Fine Arts Boston, Freedom Trail and Quincy Market.

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