Cheap Flights from Islip to Chicago

Compare Islip to Chicago flight deals

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Flight deals from Islip 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 ج.م.‏ 16,375. 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 June.

Islip to Chicago: Flight information

The things to know before you go.
Cheapest flight foundج.م.‏ 8,514
Cheapest month to flyJune

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 ج.م.‏ 16,025. 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 ج.م.‏ 16,025.
As of June 2026, there are no flights flying from Islip to Chicago.
The cheapest month to fly from Islip to Chicago is usually June.
If you're flying from Islip Airport, the cheapest airport near Chicago is Chicago Rockford – which is 126.2 km away from the centre of Chicago. We've found flights into this airport from ج.م.‏ 16,025.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Islip Airport to Chicago on Friday, 26 June 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 June, the average temperature is usually around 19°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

  • The timezone in Chicago is UTC-6. The city is one hour behind Islip, where Long Island MacArthur Airport is located.

  • For a relaxed start to your ISP to Chicago flight, leave plenty of time to navigate the airport and find your gate. Turning up two hours ahead of international departures and one hour before domestic flights is the standard rule.

  • Flying during a popular month like February? School holidays and other popular periods can lead to longer queues and delays at security. Play it safe and arrive up to four hours ahead of an international flight and two hours before a domestic departure.

  • Located around 11 kilometres from central Islip, ISP can be reached in about 10 minutes by car. Travelling on public transport will take roughly 30 minutes.

  • Want a hassle-free start to your travels? Stay near ISP. Whether you're taking an early flight from Long Island MacArthur Airport to Chicago or just don't like being rushed, these hotels have you covered:

  • When it comes to the on-time performance of Long Island MacArthur Airport, data shows 76% of flights complete their journey on time.

  • You'll find ISP at 100 Arrivals Avenue.

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

  • ج.م.‏ 8,514 is the lowest price we've seen for a one-way Long Island MacArthur Airport to Chicago flight. A return plane ticket right now is ج.م.‏ 16,025. Depending on how early you book and the availability, these fares may change.

  • To find cheap flights from ISP to Chicago, book as early as possible. Airlines generally offer lower prices when tickets first go on sale.

  • The 'Whole month' search tool will show you the cheapest tickets from Long Island MacArthur Airport to Chicago across every month. It's a good way to find a bargain if your trip dates are flexible.

  • You don't need to check in daily to find out if fares have dropped when you set up a Price Alert. We'll notify you the moment there's an even bigger deal on cheap flights from ISP to Chicago.

  • Tailor your flights with filters. Pick your preferred arrival and departure times, total journey duration and airlines. You can also sort the results by 'Fastest,' 'Cheapest' or 'Best' flights from Long Island MacArthur Airport to Chicago.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) to the centre of Chicago takes around 30 minutes to reach by car. The centre is roughly 27 kilometres away.

  • Getting to the centre by public transport takes around 45 minutes.

  • Look into staying at a hotel near ORD if you have a late flight from Long Island MacArthur Airport to Chicago. Check in to one of these options and make arrival day easier:

  • Booking your vehicle from Chicago O'Hare International Airport around four weeks ahead of your flight from ISP to Chicago can help you lock in the best possible rate.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Central Chicago is around 16 kilometres from Chicago Midway International Airport (MDW). After your flight from Long Island MacArthur Airport to Chicago has landed and you've navigated your way to arrivals, expect a drive of about 25 minutes.

  • If you choose to travel on public transport, you'll reach the centre in 30 minutes or so.

  • Following your ISP to Chicago flight, kick back at a hotel near MDW. These are some great accommodation options that'll help you slip into relaxation mode:

  • Snap up a deal by securing your ride from MDW four weeks in advance. You can also expect to have a greater range of vehicles.

  • Chicago Midway International Airport is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is around 145 kilometres from central Chicago. It'll take you about 1 hour 40 minutes to reach the city centre in a taxi or ride-share once you've stepped off your flight from Long Island MacArthur Airport to Chicago.

  • Public transport will take you there in about 2 hours.

  • Stay at a hotel near RFD and go from the runway to resting in a snap. Whether you have a late ISP to Chicago flight or just want to simplify your travel plans, these accommodation options offer a quick route to a good night's sleep:

  • Booking at least a few weeks in advance of your flight from Long Island MacArthur Airport to Chicago is always smart. As well as better deals, you'll have a wider selection of vehicle makes and models at RFD.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

  • January is the quietest month for flights from Long Island MacArthur Airport to Chicago, while July is the busiest. Work out the best time to go to Chicago based on whether you want a laid-back vibe or a lively atmosphere.

  • Book a Long Island MacArthur Airport to Chicago plane ticket with a departure in July to visit the city during its warmest month. Expect temperatures to range from 16ºC to 28ºC.

  • January sees average temperatures of between -12ºC and 3ºC. Look for a cheap ticket from ISP to Chicago around that time if you'd rather travel in cooler conditions.

More about Chicago

Explore more of the United States

  • Columbus is just one of the many cities in the United States waiting to be explored after you've experienced Chicago. Around 451 kilometres away to the southeast, top sights here include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • Around 257 kilometres southeast of Chicago, Indianapolis is another favourite stop in the United States. Experience the best of this destination with a visit to Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.