Trip.com
>
Flights
>
Flights to United States
>
Flights to Illinois
>
Flights to Chicago
Hotels in Chicago
>
Flights from Islip to Chicago

Find flight deals from Islip to Chicago for the next 3 months. Book one way flights from AU$154 or round trip flights from AU$289.

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Flying from Islip to Chicago

The distance between Islip and Chicago is about 1,218.34 km. It takes around 4 hours on average to fly from Islip to Chicago. The most popular month to Chicago is July. The off-season for travel is September.

Cheapest one-way flight priceAU$154
Cheapest round-trip ticket priceAU$289
Off-season for travelSeptember
Peak season for travelJuly
Flight distance1,218.34 km
Average flight time4 hours

When is the cheapest time to fly from Islip to Chicago?

The cheapest time for Islip to Chicago flights: Nov 6 to Nov 12 — one way flight prices from AU$153.

Cheapest flights
From price
Search
  • 2329

  • Nov

    305
  • 612
  • 1319
  • 2026

  • Dec

    273
  • 410
  • 1117
  • 1824
  • 2531

  • Jan

    17
  • 814
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • How long does it take to fly from Islip (ISP) to Chicago (CHI) and what is the distance?

    It takes around 4 hours to fly from Islip (ISP) to Chicago (CHI).
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Islip to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • The cheapest months to fly from Islip to Chicago is September, when demand for travel is lower.
  • After crunching the numbers on our October flight calendar, it's currently cheapest to fly from Islip to Chicago on October 23, 2025 with Frontier Airlines, with prices starting at AU$306.
  • The time difference between Chicago and Islip is 1h.
  • Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

How to find a cheap flight from Islip to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Islip to Chicago. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
For the best booking experience on the go, download Trip.com and search for cheap flights to access exclusive deals just for you.

More Travel Options