C$108 Cheap Flights from Islip to Chicago

Compare Islip to Chicago flight deals

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

Book the best Chicago fare with no extra fees

Flight deals from Islip Airport to Chicago

Looking for a cheap last-minute deal or the best return flight from Islip Airport to Chicago? If you want to travel next month, return fares start from C$245. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Islip to Chicago

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

Islip to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$108
Cheapest month to flyApril

Finding cheap flights from Islip to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Islip to Chicago is C$245. 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 Islip to Chicago. But we found flights with one or more stops from C$245.
As of March 2026, there are no flights flying from Islip to Chicago.
The cheapest month to fly from Islip to Chicago is usually April.
If you're flying from Islip Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from C$245.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Islip Airport to Chicago on Thursday, April 16, 2026.
No airlines currently offer direct flights between Islip Airport and Chicago. 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 Chicago 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In March, the average temperature is usually around 3°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Frontier Airlines offers the cheapest flight tickets to Chicago.

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

  • Long Island MacArthur Airport is located in Islip. Operating on the UTC-5 timezone, Chicago is 1 hour behind Islip.

  • To ensure you catch your flight from ISP to Chicago, allow plenty of time for things like baggage drop and finding your gate. Turning up two hours before international departures and one hour before domestic flights is the general travel rule.

  • Flying during a peak time like August? High seasons (like Thanksgiving, Christmas/New Year and spring break) can add another hour at check-in and security. Be extra cautious and arrive up to four hours ahead of an international flight and two hours before domestic departures.

  • Once you've booked your flight tickets from Long Island MacArthur Airport to Chicago, get your travel documents ready. A passport or visa isn't required since you're flying within United States. As long as you have another valid proof of identity, like an ID card or driver's licence, you're all set.

  • The journey from central Islip to ISP takes about 1 hour and 11 minutes on public transport. If you drive, ride-share or get a cab, you'll cover the 16 kilometres in 17 minutes or so, depending on traffic.

  • After a relaxed start to your travels? Stay near ISP. Whether you're catching an early flight from Long Island MacArthur Airport to Chicago or just don't like being rushed, these hotels are just the thing:

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

  • The best price we've seen for a one-way ticket from Long Island MacArthur Airport to Chicago is C$108. The cheapest price for a return flight is C$245. Remember fares may change due to availability at the time of booking.

  • To pick up cheap tickets from ISP to Chicago, book ahead. Airlines usually offer the most competitive fares when flights are first made available.

  • If you can be flexible with your trip dates, try using the 'Whole month' tool. It'll give you the cheapest price across each month when looking for your ticket from Long Island MacArthur Airport to Chicago.

  • Sign into your online account or use the app to set up a Price Alert. You'll get notified straight away if there's a better deal on this route. It's simple to do, and it'll save you from searching for cheap tickets from ISP to Chicago every day.

  • Make the most of the filters to find your ideal trip. To see the 'Cheapest,' 'Fastest' or 'Best' flights from Long Island MacArthur Airport to Chicago, use the 'Sort by' tool. You can also filter by airline, departure and arrival times, and number of stops.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to central Chicago is approximately 40 kilometres. It takes about 35 minutes to reach the centre driving.

  • It typically takes 54 minutes if you're travelling by public transport.

  • If you're arriving on a late flight from Long Island MacArthur Airport to Chicago, nothing beats the convenience of staying near the terminal. Grab your bags from the carousel and then be showered and relaxing soon after at one of these accommodation options near ORD:

Chicago Midway International Airport (MDW)

Best time to go to Chicago

  • It's time to figure out your trip dates for your flight from Long Island MacArthur Airport to Chicago. August is the busiest month to travel to Chicago. If you like a more relaxed vibe, go in February.

  • The warmest month in Chicago is July, with the temperature ranging between 15ºC and 29ºC. Lock in your flights from Long Island MacArthur Airport to Chicago in this month if this is the type of weather you enjoy.

  • If you'd rather travel in cooler conditions, search for a cheap flight from ISP to Chicago in January when temperatures average between -12ºC and 3ºC.

More about Chicago

  • Start your Chicago trip right by choosing the perfect place to stay. Once you've booked your flight from Long Island MacArthur Airport to Chicago, check out our selection of hotels including:

  • There are so many things to explore in this city it can be difficult to know where to begin. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are highlights which should be on every Chicago itinerary.

Complete your Chicago trip with a car rental

  • Finding you a cheap flight from Long Island MacArthur Airport to Chicago isn't the only thing we're good at. Check out our car rentals in Chicago and see the sights your way. We search for deals from trusted car rental providers and put them all in one place. You can instantly compare offers and then book with no fees.

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