Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Islip, New York to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Frontier flights from Islip, New York to Chicago
Our best Frontier deals on Islip, New York to Chicago flight tickets
Southwest flights from Islip, New York to Chicago
Our best Southwest deals on Islip, New York to Chicago flight tickets
See travel insights to Chicago from
How to get the cheapest flight ticket from Islip, New York to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Islip, New York and Chicago?
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $286. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Islip, New York to Chicago for around $374.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Islip, New York to Chicago during this time can be as low as $238. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $339.
What is the cheapest airline that flies from Islip Long Island to Chicago?
Frontier and Southwest are the most popular carriers operating from Islip Long Island to Chicago
What airlines fly to Chicago?
American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from Islip, New York according to our data. American Airlines is the first choice among our users, with 35% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
When to book flights from Islip, New York to Chicago
Cheap Islip, New York to Chicago (ISP to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Islip, New York to Chicago
How far is Islip Long Island to Chicago by plane?
The distance between Islip Long Island and Chicago is about 751.1 mi. Typically, this will take 6h 25m by plane in normal conditions.
When did momondo last update prices for flights from Islip Long Island Airport to Chicago?
Prices for flights from Islip Long Island Airport to Chicago refresh daily.
How many operators does momondo search for flights from Islip Long Island Airport to Chicago?
As of June 2025, there is 1 operator available to choose from for flights from Islip Long Island Airport to Chicago.
How old do you have to be to fly from Islip Long Island Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Islip Long Island Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular airline from Islip, New York to Chicago?
Based on momondo bookings for flights between Islip, New York and Chicago, the leading airline is Southwest, making up 100% of the total bookings.
Best airlines flying from Islip, New York to Chicago
Compare and see reviews for airlines that fly from Islip, New York to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $336 | Free Cancellation | Rating 8.0 4,287 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Islip to Chicago?
It is quick and easy to find Islip to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Islip to Chicago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Islip to Chicago flights to just show those with flexible booking policies.
How can momondo help me find flights from Islip to Chicago?
momondo helps you find the best flight between Islip and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Islip to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Islip are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.