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Cheap flights from Chicago to New York from $90

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to New York departing on 9/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Frontier Logo
8:49 pm - 10:40 amORD-ISP
12h 51m1 stop
Frontier Logo
11:25 am - 7:44 pmISP-ORD
9h 19m1 stop
$206Frontier
Find Deal
Thu, Sep 25 - Sun, Sep 28
Frontier Logo
8:14 am - 8:52 pmORD-ISP
11h 38m1 stop
Frontier Logo
9:37 pm - 7:34 amISP-ORD
10h 57m1 stop
$211Frontier
Find Deal
Sun, Oct 12 - Thu, Oct 16
Frontier Logo
3:18 pm - 8:54 amORD-ISP
16h 36m2 stops
Frontier Logo
11:40 am - 11:29 pmISP-ORD
12h 49m2 stops
$249Frontier
Find Deal
Thu, Nov 6 - Sat, Nov 8
Frontier Logo
8:49 pm - 10:40 amORD-ISP
12h 51m1 stop
Frontier Logo
11:40 am - 7:44 pmISP-ORD
9h 04m1 stop
$258Frontier
Find Deal
Mon, Sep 22 - Thu, Sep 25
Logo
5:46 pm - 1:39 pmORD-ISP
18h 53m2 stops
Logo
11:25 am - 7:44 pmISP-ORD
9h 19m1 stop
$269
Find Deal
Wed, Sep 24 - Sun, Sep 28
Frontier Logo
8:49 pm - 10:55 amORD-ISP
13h 06m1 stop
Frontier Logo
11:25 am - 7:44 pmISP-ORD
9h 19m1 stop
$274Frontier
Find Deal
Fri, Oct 3 - Sun, Oct 5
Southwest Logo
1:50 pm - 11:45 pmORD-ISP
8h 55m1 stop
Southwest Logo
5:25 am - 11:50 amISP-ORD
7h 25m1 stop
$402Southwest
Find Deal
Fri, Oct 10 - Sun, Oct 12
Southwest Logo
1:50 pm - 11:45 pmORD-ISP
8h 55m1 stop
Southwest Logo
5:25 am - 11:50 amISP-ORD
7h 25m1 stop
$412Southwest
Find Deal
Fri, Oct 10 - Sun, Oct 19
Southwest Logo
12:40 pm - 9:35 pmORD-ISP
7h 55m2 stops
Southwest Logo
5:25 am - 3:20 pmISP-ORD
10h 55m2 stops
$438Southwest
Find Deal
Sat, Oct 11 - Sun, Oct 12
Southwest Logo
1:50 pm - 11:45 pmORD-ISP
8h 55m1 stop
Southwest Logo
5:25 am - 4:25 pmISP-ORD
12h 00m2 stops
$449Southwest
Find Deal
Fri, Oct 10 - Sun, Oct 19

Southwest flights from Chicago to Islip

Our best Southwest deals on Chicago to Islip flight tickets
Southwest
Oct 10
ORD1:50 pmChicago O'Hare Intl
8h 55m
1 stop
ISP11:45 pmIslip Long Island
Oct 12
ISP5:25 amIslip Long Island
7h 25m
1 stop
ORD11:50 amChicago O'Hare Intl
$402
Find similar
Southwest
Oct 10
ORD1:50 pmChicago O'Hare Intl
8h 55m
1 stop
ISP11:45 pmIslip Long Island
Oct 19
ISP5:25 amIslip Long Island
7h 25m
1 stop
ORD11:50 amChicago O'Hare Intl
$412
Find similar
Southwest
Oct 11
ORD12:40 pmChicago O'Hare Intl
7h 55m
2 stops
ISP9:35 pmIslip Long Island
Oct 12
ISP5:25 amIslip Long Island
10h 55m
2 stops
ORD3:20 pmChicago O'Hare Intl
$438
Find similar

Frontier flights from Chicago to Islip

Our best Frontier deals on Chicago to Islip flight tickets
Frontier
Sep 25
ORD8:49 pmChicago O'Hare Intl
12h 51m
1 stop
ISP10:40 amIslip Long Island
Sep 28
ISP11:25 amIslip Long Island
9h 19m
1 stop
ORD7:44 pmChicago O'Hare Intl
$206
Find similar
Frontier
Oct 12
ORD8:14 amChicago O'Hare Intl
11h 38m
1 stop
ISP8:52 pmIslip Long Island
Oct 16
ISP9:37 pmIslip Long Island
10h 57m
1 stop
ORD7:34 amChicago O'Hare Intl
$211
Find similar
Frontier
Sep 25
ORD8:49 pmChicago O'Hare Intl
12h 51m
1 stop
ISP10:40 amIslip Long Island
Oct 2
ISP11:40 amIslip Long Island
9h 04m
1 stop
ORD7:44 pmChicago O'Hare Intl
$218
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Islip that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Chicago to Islip that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 9/25

8:49 pm-10:40 am

1 stop12h 51m

Islip Long Island

Sun 9/28

11:25 am-7:44 pm

1 stop9h 19m

$206

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sun 10/12

8:14 am-8:52 pm

1 stop11h 38m

Islip Long Island

Thu 10/16

9:37 pm-7:34 am

1 stop10h 57m

$211

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 11/6

3:18 pm-8:54 am

2 stops16h 36m

Islip Long Island

Sat 11/8

11:40 am-11:29 pm

2 stops12h 49m

$249

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 9/22

8:49 pm-10:40 am

1 stop12h 51m

Islip Long Island

Thu 9/25

11:40 am-7:44 pm

1 stop9h 04m

$258

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Wed 9/24

5:46 pm-1:39 pm

2 stops18h 53m

Islip Long Island

Sun 9/28

11:25 am-7:44 pm

1 stop9h 19m

$269

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Fri 10/3

8:49 pm-10:55 am

1 stop13h 06m

Islip Long Island

Sun 10/5

11:25 am-7:44 pm

1 stop9h 19m

$274

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Fri 10/10

1:50 pm-11:45 pm

1 stop8h 55m

Islip Long Island

Sun 10/12

5:25 am-11:50 am

1 stop7h 25m

$402

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Fri 10/10

1:50 pm-11:45 pm

1 stop8h 55m

Islip Long Island

Sun 10/19

5:25 am-11:50 am

1 stop7h 25m

$412

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 10/11

12:40 pm-9:35 pm

2 stops7h 55m

Islip Long Island

Sun 10/12

5:25 am-3:20 pm

2 stops10h 55m

$438

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Fri 10/10

1:50 pm-11:45 pm

1 stop8h 55m

Islip Long Island

Sun 10/19

5:25 am-4:25 pm

2 stops12h 00m

$449

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to New York from

How to get the cheapest flight ticket from Chicago to Islip

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 Chicago and Islip?

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

On average, the least expensive day to fly to Islip from Chicago is on a Thursday. momondo users have found tickets for Thursday departures for as low as $223. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago to Islip on a Wednesday will generally be more expensive and average around $416. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Flying to Islip 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 in the morning are often more expensive with an average ticket price of $369.

When to book flights from Chicago to Islip

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Islip according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

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

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

Direct flights

None
There are no direct flights from Chicago to Islip. There are no popular flight routes from Chicago to Islip.
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 22m.

  • 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?

  • 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?

Best airlines flying from Chicago to Islip

Compare and see reviews for airlines that fly from Chicago to Islip with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $254Free CancellationRating
8.0
4,248 reviews
Search Southwest flights

Traveling to a place near New York?

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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.

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