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Cheap flights from Chicago to New York from $81

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 5/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Find the cheapest flights from Chicago to New York

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:00 am - 9:13 am
ORD
-
ISP
26h 13m
1 stop
Frontier Logo
11:12 am - 11:13 pm
ISP
-
ORD
13h 01m
1 stop
$218Frontier
Sun, May 3 - Thu, May 7
Frontier Logo
6:00 am - 9:13 am
ORD
-
ISP
26h 13m
1 stop
Frontier Logo
11:12 am - 8:32 pm
ISP
-
ORD
34h 20m
2 stops
$250Frontier
Sun, May 3 - Thu, May 7
Multiple Airlines Logo
5:50 am - 7:36 pm
ORD
-
ISP
12h 46m
2 stops
Multiple Airlines Logo
8:31 pm - 12:23 pm
ISP
-
ORD
16h 52m
1 stop
$257Multiple Airlines
Fri, May 1 - Mon, May 4
Multiple Airlines Logo
5:05 am - 7:36 pm
ORD
-
ISP
13h 31m
2 stops
Multiple Airlines Logo
8:31 pm - 6:24 pm
ISP
-
ORD
22h 53m
1 stop
$266Multiple Airlines
Mon, Apr 27 - Fri, May 1
Frontier Logo
5:30 pm - 10:05 am
ORD
-
ISP
15h 35m
1 stop
Frontier Logo
11:12 am - 11:13 pm
ISP
-
ORD
13h 01m
1 stop
$279Frontier
Thu, May 14 - Thu, May 21
Frontier Logo
5:30 pm - 10:05 am
ORD
-
ISP
15h 35m
1 stop
Frontier Logo
11:12 am - 11:13 pm
ISP
-
ORD
13h 01m
1 stop
$299Frontier
Fri, May 8 - Sun, May 10
Multiple Airlines Logo
3:44 pm - 6:14 pm
ORD
-
ISP
25h 30m
2 stops
Multiple Airlines Logo
11:12 am - 11:13 pm
ISP
-
ORD
13h 01m
1 stop
$301Multiple Airlines
Thu, May 14 - Thu, May 21
Frontier Logo
8:00 am - 9:13 am
ORD
-
ISP
24h 13m
1 stop
Frontier Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
$309Frontier
Sat, May 2 - Wed, May 6
Multiple Airlines Logo
10:49 am - 10:27 am
ORD
-
ISP
22h 38m
1 stop
Multiple Airlines Logo
2:08 pm - 12:23 pm
ISP
-
ORD
23h 15m
2 stops
$310Multiple Airlines
Wed, May 20 - Tue, May 26
Multiple Airlines Logo
8:30 am - 6:14 pm
ORD
-
ISP
8h 44m
1 stop
Multiple Airlines Logo
5:50 pm - 12:23 pm
ISP
-
ORD
19h 33m
2 stops
$315Multiple Airlines
Fri, May 15 - Sun, May 17

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Frontier flights from Chicago to Islip, New York

Our best Frontier deals on Chicago to Islip, New York flight tickets
Frontier
May 3
ORD6:00 amChicago O'Hare Intl
26h 13m
1 stop
ISP9:13 amIslip Long Island
May 7
ISP11:12 amIslip Long Island
13h 01m
1 stop
ORD11:13 pmChicago O'Hare Intl
$218
Frontier
May 3
ORD6:00 amChicago O'Hare Intl
26h 13m
1 stop
ISP9:13 amIslip Long Island
May 7
ISP11:12 amIslip Long Island
34h 20m
2 stops
ORD8:32 pmChicago O'Hare Intl
$250
Frontier
May 14
ORD5:30 pmChicago O'Hare Intl
15h 35m
1 stop
ISP10:05 amIslip Long Island
May 21
ISP11:12 amIslip Long Island
13h 01m
1 stop
ORD11:13 pmChicago O'Hare Intl
$279

Southwest flights from Chicago to Islip, New York

Our best Southwest deals on Chicago to Islip, New York flight tickets
Southwest
May 20
ORD1:35 pmChicago O'Hare Intl
8h 05m
1 stop
ISP10:40 pmIslip Long Island
May 26
ISP6:55 amIslip Long Island
12h 30m
1 stop
ORD6:25 pmChicago O'Hare Intl
$340
Southwest
May 20
ORD11:55 amChicago O'Hare Intl
9h 15m
2 stops
ISP10:10 pmIslip Long Island
May 26
ISP2:30 pmIslip Long Island
8h 25m
2 stops
ORD9:55 pmChicago O'Hare Intl
$345
Southwest
May 23
ORD3:15 pmChicago O'Hare Intl
6h 25m
1 stop
ISP10:40 pmIslip Long Island
May 27
ISP12:30 pmIslip Long Island
10h 25m
2 stops
ORD9:55 pmChicago O'Hare Intl
$360

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Islip, New York 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 April 17, 2026.
Use the filters below to find and compare flights from Chicago to Islip, New York that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sun 5/3

6:00 am-9:13 am

1 stop26h 13m

Islip Long Island

Thu 5/7

11:12 am-11:13 pm

1 stop13h 01m

$218

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sun 5/3

6:00 am-9:13 am

1 stop26h 13m

Islip Long Island

Thu 5/7

11:12 am-8:32 pm

2 stops34h 20m

$250

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Fri 5/1

5:50 am-7:36 pm

2 stops12h 46m

Islip Long Island

Mon 5/4

8:31 pm-12:23 pm

1 stop16h 52m

$257

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 4/27

5:05 am-7:36 pm

2 stops13h 31m

Islip Long Island

Fri 5/1

8:31 pm-6:24 pm

1 stop22h 53m

$266

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 5/14

5:30 pm-10:05 am

1 stop15h 35m

Islip Long Island

Thu 5/21

11:12 am-11:13 pm

1 stop13h 01m

$279

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Fri 5/8

5:30 pm-10:05 am

1 stop15h 35m

Islip Long Island

Sun 5/10

11:12 am-11:13 pm

1 stop13h 01m

$299

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 5/14

3:44 pm-6:14 pm

2 stops25h 30m

Islip Long Island

Thu 5/21

11:12 am-11:13 pm

1 stop13h 01m

$301

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 5/2

8:00 am-9:13 am

1 stop24h 13m

Islip Long Island

Wed 5/6

11:00 am-11:13 pm

1 stop13h 13m

$309

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Wed 5/20

10:49 am-10:27 am

1 stop22h 38m

Islip Long Island

Tue 5/26

2:08 pm-12:23 pm

2 stops23h 15m

$310
Quickest round-trip

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Fri 5/15

8:30 am-6:14 pm

1 stop8h 44m

Islip Long Island

Sun 5/17

5:50 pm-12:23 pm

2 stops19h 33m

$315

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, 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

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

What airlines fly to Islip, New York?

United Airlines, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Islip, New York from Chicago according to our data. United Airlines is the first choice among our users, with 46% 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.

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

Fastest flight time

7h 54m

Direct flights

None
The fastest flight from Chicago to Islip, New York takes 7h 54m
There are no direct flights from Chicago to Islip, New York. There are no popular flight routes from Chicago to Islip, New York.
Search flight deals

Frequently asked questions about flying from Chicago to Islip, New York

  • 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 54m.

  • 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 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?

Traveling to a place near New York?

Book flights to New York if you plan to visit one of these locations
Montauk
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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.

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