Cheap Flights from Islip (ISP) to Chicago (CHIA)

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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.

Alternative Islip to Chicago routes

Looking for the cheapest, fastest or easiest route from Islip to Chicago? You could fly into the following airports instead.

Islip to Chicago: Flight information

The things to know before you go.
Cheapest flight found$112
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 round-trip flight from Islip to Chicago is $271. 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 $271.
There are no flights flying from Islip to Chicago, as of June 2025.
The cheapest month to fly from Islip to Chicago is usually June 2025.
If you're flying from Islip Airport, the cheapest airport near Chicago is Chicago Midway – which is 9.0 miles away from the center of Chicago. We've found flights to this airport from $271.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Islip Airport to Chicago on Friday, June 20, 2025.
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 66°F. July is typically the warmest month in Chicago, when it usually averages around 80°F. You can expect the least rain in January. The coldest month is January, with temperatures averaging 18°F. 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-5. The city is one hour behind Islip, where Long Island MacArthur Airport is located.

  • To avoid missing your ISP to Chicago flight, allow plenty of time to check in and drop off your luggage. Arriving two hours ahead of international departures and an hour before domestic flights is the general travel rule.

  • If you're traveling during a major holiday or another peak period, allow extra time. A good rule is two hours ahead of domestic flights and up to four hours before international departures. Check-in and security lines will be longer.

  • Located around 7 miles from the center of Islip, ISP can be reached in about 15 minutes by car (depending on traffic). The journey on public transport takes roughly 1 hour 10 minutes.

  • Searching for a hotel close to ISP? If you're boarding an early flight from Long Island MacArthur Airport to Chicago, these stays put the terminal practically at your doorstep:

  • When it comes to Long Island MacArthur Airport's on-time performance, 77.45% of flights stick to their scheduled arrival time.

  • You'll find ISP at 100 Arrivals Avenue.

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

  • $112 is the lowest price we've seen for a one-way Long Island MacArthur Airport to Chicago flight. A round-trip plane ticket right now is $271. Depending on how early you book and the availability, these fares may change.

  • Don't wait until the last moment. You're more likely to pick up cheap flights from ISP to Chicago if you book early. Airlines often have some great early bird deals.

  • If you have flexibility with your trip dates, try using the 'Whole month' search tool. It'll find the cheapest price across each month when searching for a Long Island MacArthur Airport to Chicago ticket.

  • You don't need to check in daily to see if fares have dropped when you create a Price Alert. We'll update you as soon as there's an even bigger deal on cheap flights from ISP to Chicago.

  • Pick your ideal arrival and departure times, number of stops and airlines with our filters. Then, sort the results for your flight from Long Island MacArthur Airport to Chicago by 'Best,' 'Fastest' or 'Cheapest.'

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to the center of Chicago takes about 35 minutes by car. The center is roughly 25 miles away.

  • Getting there by public transport takes about 55 minutes.

  • The last thing you want is a lengthy journey to your hotel if you're getting in late on a flight from Long Island MacArthur Airport to Chicago. Stay at one of these accommodation options near ORD instead:

  • Hit the road running by picking up an O'Hare International Airport rental car. Grab your wheels from Routes Car Rentals, Dollar or Budget and explore beyond Chicago's usual tourist stops.

  • Reserving your ride from O'Hare International Airport around four weeks ahead of your flight from ISP to Chicago can help you lock in the lowest rate.

  • The street address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Once your flight from Long Island MacArthur Airport to Chicago has arrived, you can get to the city center in around 20 minutes by car. Central Chicago is roughly 12 miles from Chicago Midway International Airport (MDW).

  • If you travel by public transport, the ride to the center takes 45 minutes or so.

  • Following your ISP to Chicago flight, tuck yourself in at a hotel close to MDW. These are some great accommodation options that'll help you sink into relaxation mode:

  • Dollar, Hertz and Budget make picking up a Chicago Midway International Airport rental car simple. These providers are located in or around the terminal and will have you ready to go in a flash.

  • Lock in the best price by booking your ride from MDW four weeks in advance. You can also expect to have a bigger selection of vehicles.

  • Chicago Midway International Airport can be found at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Hop off your flight from Long Island MacArthur Airport to Chicago and head for your hotel or start taking in the sights right away. The center of Chicago is around 85 miles from Chicago Rockford International Airport (RFD) and typically takes 1 hour 25 minutes to reach by car.

  • If you go by public transport, the journey takes about 4 hours 15 minutes.

  • Reserve 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 keep your travel plans simple, these accommodation options will have you settling in quickly:

  • Stay in control of the next leg of your journey by picking up a Chicago Rockford International Airport rental car. Budget, Alamo and National will get you on the road.

  • Booking at least a few weeks in advance of your flight from Long Island MacArthur Airport to Chicago is a smart move. As well as better prices, you'll be able to choose the vehicle make and model you prefer at RFD.

  • Chicago Rockford International Airport's address is 2 Airport Cir.

Best time to go to Chicago

  • Travel to Chicago during high season if you like a bustling atmosphere, but remember that prices are generally higher. Alternatively, book your flights from Long Island MacArthur Airport to Chicago in the low season when prices are cheaper and it's not as busy.

  • The warmest month in Chicago is July, with temperatures ranging between 59ºF and 84ºF. Lock in your Long Island MacArthur Airport to Chicago plane ticket then if this is the type of weather you enjoy.

  • January sees average temperatures of between 10ºF and 37ºF. Look for a cheap ticket from ISP to Chicago around that time if you like traveling in cooler conditions.

More about Chicago

  • When it comes to looking for somewhere to lay your head, you'll find the best stays in Chicago right here. Browse these hotels once you've booked your flight from Long Island MacArthur Airport to Chicago:

  • Art Institute of Chicago and Millennium Park are just a couple of the leading attractions to add to your Chicago travel itinerary. Keep the adventure rolling by checking out LandShark Beer Garden at Navy Pier.

Explore more of United States

  • Chicago has its own special appeal, but there are so many other parts of United States you should also see. Around 280 miles south-east of Chicago, a trip to Columbus will keep you busy. Don't miss top attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another standout destination in United States and is around 160 miles south-east of Chicago. No trip is complete without dropping by The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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