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This Weekend's Flight Deals to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fares from $45 One Way, $105 Round Trip from Islip to Chicago

Prices starting at $105 for return flights and $45 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

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More About Flying To Chicago from Islip

Route Information for Flights from Islip to Chicago

Origin Airport IATA CodeNYC
Destination Airport IATA CodeCHI
Distance737 mi
Direct Flight AirlinesKLM, Kenya Airways, Delta Air Lines, Alitalia, Korean Air, Virgin Atlantic
Earliest Flight Arrival4:09PM UTC
Latest Flight Arrival11:29PM UTC

Flights Review

Mar 1, 2020

Service was excellent. The flight was smooth

Feb 20, 2020

Always a pleasure flying with Delta. Staff is family-friendly too

Feb 19, 2020

Not that pleased with check in, had to check carry ons even though we had room in 1st class. The service was mediocre at best...I feel we would have had the same service on Business...

Feb 18, 2020

Love the free carryon

Feb 13, 2020

I'm still waiting for my luggage to make it, but I'm home safe and sound!

Feb 12, 2020

I’m not one who enjoys flying; it’s a necessary evil, but my 2 American Airlines flights were a breeze. I managed to sleep during the duration of the flight. The free internet was a plus, but it was especially slow so I didn’t use while I was awake and able b

Feb 5, 2020

I am a tall person. (6'0" )This flight had tight quarters and was tolerable for a 2 hr flight. I could see how others might have trouble.

Jan 31, 2020

Keep up the good work.

Jan 30, 2020

Friendly staff

Jan 25, 2020

Nothing else for a short flight

Flying from Islip to Chicago

Islip Airport Information

Searching for low fares on flights from Islip can be time consuming, but Orbitz.com can help you save time and money. It compares and presents you with the rates of the airlines providing service to the airport, allowing you to choose the best rate for your budget and needs. The Long Island MacArthur Airport is the major airport serving Islip and its surrounding communities. It is located at 100 Arrival Avenue in Ronkonkoma and is about seven miles from downtown. Southwest Airlines and US Airways Express provide domestic and international flights. You will always receive the best air rates on Orbitz.com.

Transportation to the Airport

Alamo, National, Hertz, Budget, Avis, and Enterprise are the car rental companies located in the baggage claim area. Their rates vary by company and type of vehicle chosen. Orbitz.com works with these companies to give you the lowest rate available. Metered taxi service is also available. Public transportation is available for $1.50 from one of many bus stops to the airport.

Airport Parking Information

The airport has short-term, long-term, and economy parking located near the terminals. The short-term lots will cost $3 an hour, with a daily maximum rate of $25; the long-term rates are $4 an hour, with a maximum daily rate of $14. Economy parking is available for $4 an hour or a daily rate of $12.50. A cell phone lot is an option for picking up or dropping off passengers for free.

Airport Restaurant Information

The food court has several dining options for passengers, including Starbucks, Phillips' Crabs, Maggie O'Shea's, A&W, and the Great American Bagel and Bakery. You will find an assortment of breakfast, lunch, and dinner menu items. When you are searching for flights from Islip, check with Orbitz.com for the best rates on airfare and ground transportation.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Flights from Islip to Chicago - Frequently Asked Questions

What is the shortest flight from Islip to Chicago?

Traveling from Islip, NY (ISP-MacArthur) to Chicago, IL (MDW-Midway Intl.) takes at least 3 hours and 5 minutes. Enjoy a beverage and watch a movie or two — it's the ideal opportunity to chill out.

If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Chicago with flexible change policies?

In most cases you'll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2019 shows that Tuesday is the cheapest day to depart, followed by Monday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a fresh start to the new year. Be aware that the most expensive time to fly isn't the height of summer, as most people assume, but the festive month of December.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2019 saved over 50% on their airfares. Get mixing and matching today!

*According to flight demand on Orbitz.com from January to December 2019. Savings are subject to change based on departure location, date and destination.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.