Cheap Flights from Chicago O'Hare International to Islip

Compare Chicago O'Hare International to Islip flight deals

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

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Flight deals from Chicago O'Hare International Airport to Islip Airport

Looking for a cheap last-minute deal or the best return flight from Chicago O'Hare International Airport to Islip Airport? If you want to travel next month, return fares start from $633. Find the lowest prices on one-way and return tickets right here.

Islip.$633 per passenger.Departing Wed, 15 Apr, returning Sun, 19 Apr.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago O'Hare International on Wed, 15 Apr, arriving in Islip.Inbound indirect flight with Southwest Airlines, departs from Islip on Sun, 19 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From $633, select.

Islip.$660 per passenger.Departing Thu, 23 Jul, returning Sun, 26 Jul.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago O'Hare International on Thu, 23 Jul, arriving in Islip.Inbound indirect flight with Southwest Airlines, departs from Islip on Sun, 26 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From $660, select.

Islip.$678 per passenger.Departing Wed, 1 Jul, returning Sat, 8 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago O'Hare International on Wed, 1 Jul, arriving in Islip.Inbound indirect flight with Southwest Airlines, departs from Islip on Sat, 8 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $678, select.

Islip.$753 per passenger.Departing Fri, 21 Aug, returning Mon, 24 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago O'Hare International on Fri, 21 Aug, arriving in Islip.Inbound indirect flight with Southwest Airlines, departs from Islip on Mon, 24 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $753, select.

Islip.$816 per passenger.Departing Tue, 24 Mar, returning Thu, 26 Mar.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago O'Hare International on Tue, 24 Mar, arriving in Islip.Inbound indirect flight with Southwest Airlines, departs from Islip on Thu, 26 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From $816, select.

Find the cheapest month to fly from Chicago O'Hare International to Islip

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

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Chicago O'Hare International to Islip: Alternative routes

Compare routes from Chicago O'Hare International to Islip below. You may find an airport to fly into that's cheaper, faster, or easier than Islip.

Chicago to Islip: Flight information

The things to know before you go.

Cheapest flight found	$633
Cheapest month to fly	April

Finding cheap flights from Chicago O'Hare International to Islip: Frequently asked questions

How much are return flights from Chicago O'Hare International to Islip?

The best price we found for a return flight from Chicago O'Hare International to Islip is $633. 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.

Which airlines fly direct from Chicago O'Hare International to Islip?

Currently, there are no airlines that fly direct from Chicago O'Hare International to Islip. But we found flights with one or more stops from $633.

How many flights are there a week from Chicago O'Hare International to Islip?

As of March 2026, there are no flights flying from Chicago O'Hare International to Islip.

When is the cheapest time to fly from Chicago O'Hare International to Islip?

The cheapest month to fly from Chicago O'Hare International to Islip is usually April.

Which upcoming date is cheapest to fly from Chicago O'Hare International Airport to Islip Airport on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago O'Hare International Airport to Islip Airport on Wednesday, 15 April 2026.

Can I get a direct flight from Chicago O'Hare International Airport to Islip Airport?

No airlines currently offer direct flights between Chicago O'Hare International Airport and Islip Airport. Most routes have one or more stops.

How can I find the best flight deal to Islip?

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.

When is the best time to book flights to Islip?

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.

Which is the cheapest airline to fly from Chicago O'Hare International Airport to Islip with?

Currently, Southwest Airlines offers the cheapest flight tickets to Islip.

Flying from O'Hare International Airport (ORD) to Long Island MacArthur Airport (ISP): what you need to know

To ensure you catch your ORD to ISP flight, allow plenty of time to check in and drop off your luggage. Turning up two hours before international departures and one hour before domestic flights is the general travel rule.
You can expect longer lines in popular months like August. Arriving up to four hours in advance for an international flight and two hours for a domestic departure will give you ample time for security and boarding.
If you want to break up your flight, simply uncheck 'Direct flights only' when searching for your ticket from O'Hare International Airport to Long Island MacArthur Airport. Here are the top stopovers between ORD and ISP:
- Baltimore/Wash International Thurgood Marshall Airport
- Raleigh-Durham International Airport
- Portland International Jetport Airport

How to find the cheapest flights from O'Hare International Airport (ORD) to Long Island MacArthur Airport (ISP)

$309 is the best price for a one-way O'Hare International Airport to Long Island MacArthur Airport flight. A return flight starts from $633. These fares can change based on availability and demand.
It's a good idea to book early if you're hoping to get cheap tickets from ORD to ISP. That's because flight prices are based on demand, which tends to increase closer to the date of departure.
If you're willing to be flexible with your travel dates, use the 'Whole month' search tool. It'll show you the lowest price across the month when searching for a flight from O'Hare International Airport to Long Island MacArthur Airport.
Picking up cheap flights from ORD to ISP is easy with Price Alerts. All you need to do is set up one of these automatic alerts and we'll notify you as soon as a new deal comes up.
Discover the right flight for you by using the filters. To see the 'Best,' 'Fastest' or 'Cheapest' flights from O'Hare International Airport to Long Island MacArthur Airport, use the 'Sort by' function. You can also filter by arrival and departure times, airline, and number of stops.

Handy information about O'Hare International Airport (ORD)

ORD is located at 10000 West O'Hare.
Of the flights that depart from O'Hare International Airport, 74.85% touch down on time at their destination.
To reach O'Hare International Airport from central Chicago, it takes about 35 minutes if you're planning to drive. This depends on traffic, however. It's approximately 40 kilometres from the airport to the city centre.
You can expect a journey time of roughly 55 minutes on public transport.
Looking for a convenient hotel near ORD? If you're boarding an early flight from O'Hare International Airport to Long Island MacArthur Airport, these stays will put you moments from check-in:

Arriving at Long Island MacArthur Airport (ISP)

The last thing you need is a lengthy journey to your hotel if you're getting in late on an O'Hare International Airport to Long Island MacArthur Airport flight. Book one of these accommodation options near ISP instead:
Say yes to new adventures by picking up a Long Island MacArthur Airport rental car. Grab your wheels from Enterprise, Budget or Avis and explore beyond Islip's usual tourist stops.
Give yourself a better shot at getting a great price by booking as soon as possible. Reserving your ride from Long Island MacArthur Airport at least a few weeks in advance is a good move.

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

ISP is located at 100 Arrivals Avenue.
Long Island MacArthur Airport is roughly 16 kilometres from the centre of Islip. Driving there takes about 15 minutes.
If you're using public transport, expect a journey time of around 1 hour 10 minutes.

When to fly to Long Island MacArthur Airport (ISP)

It's time to pick your trip dates for your flight from O'Hare International Airport to Long Island MacArthur Airport. August is the most popular month to visit Islip. If you like a more relaxed vibe, go in May.
The warmest month in Islip is July, with temperatures ranging between 19ºC and 29ºC. Lock in your flights from O'Hare International Airport to Long Island MacArthur Airport in this month if this is the kind of weather you like.
If you want cooler conditions, search for a cheap ticket from ORD to ISP in January. Average temperatures are between -4ºC and 8ºC then.

Explore more of United States

Islip has loads to offer, but there are so many other parts of United States waiting to be discovered. Around 64 kilometres west of Islip, a trip to New York will keep you busy. Check out popular attractions like Statue of Liberty, Central Park and Empire State Building.
Philadelphia is another favourite destination in United States and is around 193 kilometres south-west of Islip. No journey is complete without a visit to Liberty Bell, Independence Hall and Philadelphia Museum of Art.