What airlines fly to Islip, New York?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Islip, New York from Chicago according to our data. American Airlines is the first choice among our users, with 34% of people opting to fly with this airline when traveling to Islip, New York. Keep in mind that there are 7 different airlines that fly to Islip, New York on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Chicago to Islip Long Island?

Frontier and Southwest are the most popular carriers operating from Chicago to Islip Long Island

When did momondo last update prices for flights from Chicago to Islip Long Island Airport?

Prices for flights from Chicago to Islip Long Island Airport refresh daily.

How many operators does momondo search for flights from Chicago to Islip Long Island Airport?

As of August 2025, there is 1 operator available to choose from for flights from Chicago to Islip Long Island Airport.

How old do you have to be to fly from Chicago to Islip Long Island Airport?

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 Chicago to Islip Long Island Airport.

What documentation or ID do you need to fly to Islip Long Island Airport?

The travel and health documents you'll need for your trip to Islip Long Island Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Islip Long Island Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$87 Cheap Flights from Chicago to Islip in 2025

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Find the cheapest flights from Chicago to New York

Round-trip

One-way

Last minute

Cheap round-trip flights

8:49 pm - 10:40 amORD-ISP

12h 51m1 stop

11:35 am - 9:58 pmISP-ORD

11h 23m1 stop

$189

Find Deal

Mon, Sep 8 - Wed, Sep 10

8:05 am - 4:27 pmORD-ISP

7h 22m1 stop

11:40 am - 7:44 pmISP-ORD

9h 04m1 stop

$254Frontier

Find Deal

Thu, Sep 11 - Thu, Sep 18

8:49 pm - 10:40 amORD-ISP

12h 51m1 stop

11:25 am - 7:44 pmISP-ORD

9h 19m1 stop

$272Frontier

Find Deal

Thu, Sep 11 - Sun, Sep 14

6:56 am - 11:41 pmORD-ISP

15h 45m1 stop

6:05 am - 4:10 pmISP-ORD

11h 05m1 stop

$293

Find Deal

Wed, Aug 27 - Sun, Aug 31

1:30 pm - 9:40 pmORD-ISP

7h 10m1 stop

5:30 am - 1:05 pmISP-ORD

8h 35m1 stop

$295Southwest

Find Deal

Sat, Aug 30 - Wed, Sep 3

8:05 am - 4:27 pmORD-ISP

7h 22m1 stop

11:25 am - 7:44 pmISP-ORD

9h 19m1 stop

$296Frontier

Find Deal

Thu, Sep 4 - Thu, Sep 11

1:30 pm - 9:40 pmORD-ISP

7h 10m1 stop

5:30 am - 5:55 pmISP-ORD

13h 25m1 stop

$300Southwest

Find Deal

Sat, Aug 30 - Tue, Sep 2

5:16 pm - 11:41 pmORD-ISP

29h 25m1 stop

6:05 am - 4:10 pmISP-ORD

11h 05m1 stop

$304

Find Deal

Tue, Aug 26 - Sun, Aug 31

6:00 am - 2:55 pmORD-ISP

7h 55m2 stops

5:30 am - 5:55 pmISP-ORD

13h 25m1 stop

$306Southwest

Find Deal

Sat, Aug 30 - Tue, Sep 2

2:55 pm - 10:55 pmORD-ISP

7h 00m2 stops

5:30 am - 1:05 pmISP-ORD

8h 35m1 stop

$317Southwest

Find Deal

Mon, Sep 8 - Wed, Sep 10

Frontier flights from Chicago to Islip, New York

Our best Frontier deals on Chicago to Islip, New York flight tickets

Frontier

Aug 21

ORD7:46 pmChicago O'Hare Intl

12h 27m

1 stop

ISP9:13 amIslip Long Island

Aug 24

ISP9:01 pmIslip Long Island

12h 36m

1 stop

ORD8:37 amChicago O'Hare Intl

$241

Find similar

Frontier

Sep 11

ORD8:05 amChicago O'Hare Intl

7h 22m

1 stop

ISP4:27 pmIslip Long Island

Sep 18

ISP11:40 amIslip Long Island

9h 04m

1 stop

ORD7:44 pmChicago O'Hare Intl

$254

Find similar

Frontier

Aug 21

ORD7:46 pmChicago O'Hare Intl

12h 27m

1 stop

ISP9:13 amIslip Long Island

Aug 24

ISP9:01 pmIslip Long Island

14h 38m

2 stops

ORD10:39 amChicago O'Hare Intl

$264

Find similar

Southwest flights from Chicago to Islip, New York

Our best Southwest deals on Chicago to Islip, New York flight tickets

Southwest

Aug 30

ORD1:30 pmChicago O'Hare Intl

7h 10m

1 stop

ISP9:40 pmIslip Long Island

Sep 3

ISP5:30 amIslip Long Island

8h 35m

1 stop

ORD1:05 pmChicago O'Hare Intl

$295

Find similar

Southwest

Aug 30

ORD1:30 pmChicago O'Hare Intl

7h 10m

1 stop

ISP9:40 pmIslip Long Island

Sep 2

ISP5:30 amIslip Long Island

13h 25m

1 stop

ORD5:55 pmChicago O'Hare Intl

$300

Find similar

Southwest

Aug 30

ORD6:00 amChicago O'Hare Intl

7h 55m

2 stops

ISP2:55 pmIslip Long Island

Sep 2

ISP5:30 amIslip Long Island

13h 25m

1 stop

ORD5:55 pmChicago O'Hare Intl

$306

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 9/8

8:49 pm-10:40 am

1 stop12h 51m

Islip Long Island

Wed 9/10

11:35 am-9:58 pm

1 stop11h 23m

$189

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 9/11

8:05 am-4:27 pm

1 stop7h 22m

Islip Long Island

Thu 9/18

11:40 am-7:44 pm

1 stop9h 04m

$254

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 9/11

8:49 pm-10:40 am

1 stop12h 51m

Islip Long Island

Sun 9/14

11:25 am-7:44 pm

1 stop9h 19m

$272

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Wed 8/27

6:56 am-11:41 pm

1 stop15h 45m

Islip Long Island

Sun 8/31

6:05 am-4:10 pm

1 stop11h 05m

$293

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 8/30

1:30 pm-9:40 pm

1 stop7h 10m

Islip Long Island

Wed 9/3

5:30 am-1:05 pm

1 stop8h 35m

$295

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 9/4

8:05 am-4:27 pm

1 stop7h 22m

Islip Long Island

Thu 9/11

11:25 am-7:44 pm

1 stop9h 19m

$296

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 8/30

1:30 pm-9:40 pm

1 stop7h 10m

Islip Long Island

Tue 9/2

5:30 am-5:55 pm

1 stop13h 25m

$300

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Tue 8/26

5:16 pm-11:41 pm

1 stop29h 25m

Islip Long Island

Sun 8/31

6:05 am-4:10 pm

1 stop11h 05m

$304

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 8/30

6:00 am-2:55 pm

2 stops7h 55m

Islip Long Island

Tue 9/2

5:30 am-5:55 pm

1 stop13h 25m

$306

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 9/8

2:55 pm-10:55 pm

2 stops7h 00m

Islip Long Island

Wed 9/10

5:30 am-1:05 pm

1 stop8h 35m

$317

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Islip, New York

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

Prices

Airlines

What is the cheapest day to depart on your flight to Islip, New York?

The cheapest day to depart from Chicago to Islip, New York is on a Thursday. Travelers who choose to depart for Islip, New York on a Thursday will often find tickets for as low as $223. The most expensive day to fly to Islip, New York is Wednesday, with ticket prices averaging around $416.

What is the cheapest time of day to depart on your flight to Islip, New York?

Flying to Islip, New York from Chicago at noon is the least expensive time of day to depart. momondo users have found prices as low as $141 when looking at flights departing at noon. Flights to Islip, New York are more costly in the morning, with an average ticket price of $369. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

When to book flights from Chicago to Islip, New York

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Islip, New York according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Islip, New York (CHI to ISP) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Islip, New York

Best Price Found	$87
Fastest flight time	7h 00m
Direct flights	None
Airports in Islip, New York	1 airport

The best one-way flight to Islip, New York from Chicago in the past 72 hours is $87. The best round-trip flight deal from Chicago to Islip, New York found on momondo in the last 72 hours is $189.

The fastest flight from Chicago to Islip, New York takes 7h 00m

There are no direct flights from Chicago to Islip, New York. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - Islip Long Island Airport.

There is 1 airport near Islip, New York: Islip Long Island (ISP)

Search flight deals

How far is Chicago to Islip Long Island by plane?
The distance between Chicago and Islip Long Island is about 751.1 mi. By plane, this route typically takes 7h 00m.
When did momondo last update prices for flights from Chicago to Islip Long Island Airport?
Prices for flights from Chicago to Islip Long Island Airport refresh daily.
How many operators does momondo search for flights from Chicago to Islip Long Island Airport?
As of August 2025, there is 1 operator available to choose from for flights from Chicago to Islip Long Island Airport.
How old do you have to be to fly from Chicago to Islip Long Island Airport?
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 Chicago to Islip Long Island Airport.
What documentation or ID do you need to fly to Islip Long Island Airport?
The travel and health documents you'll need for your trip to Islip Long Island Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Islip Long Island Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular airline from Chicago to Islip, New York?
momondo data reveals that the most frequently booked airline on the route from Chicago to Islip, New York is Southwest, representing 100% of all bookings.

Best airlines flying from Chicago to Islip, New York

Compare and see reviews for airlines that fly from Chicago to Islip, New York with momondo

Airline	Rating	Free Cancellation	Price
Southwest	PriceFrom $254	Free Cancellation	Rating 8.0 4,244 reviews		Search Southwest flights

Montauk

Riverhead

Sag Harbor

Southampton

Amagansett

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Islip?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Islip. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Islip with flexible booking policies on momondo?

All flight searches from Chicago to Islip on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Islip?

Once all potential Chicago to Islip flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Islip right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Islip now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Islip and let you know when they change.