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Cheap flights from Chicago to New York from $121

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 4/4. 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
1 adult, Economy, 0 bags

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Find the cheapest flights from Chicago to New York

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
10:25 am - 9:13 am
ORD
-
ISP
21h 48m
1 stop
Frontier Logo
4:07 pm - 2:17 pm
ISP
-
ORD
23h 10m
1 stop
$215Frontier
Thu, May 14 - Sun, May 17
Multiple Airlines Logo
11:25 am - 11:10 am
ORD
-
ISP
22h 45m
2 stops
Multiple Airlines Logo
4:07 pm - 11:07 pm
ISP
-
ORD
8h 00m
1 stop
$310Multiple Airlines
Tue, Apr 14 - Fri, Apr 17
Southwest Logo
12:15 pm - 10:40 pm
ORD
-
ISP
9h 25m
1 stop
Southwest Logo
6:30 am - 4:05 pm
ISP
-
ORD
10h 35m
2 stops
$342Southwest
Sat, May 9 - Tue, May 12
Southwest Logo
12:15 pm - 10:40 pm
ORD
-
ISP
9h 25m
1 stop
Southwest Logo
6:55 am - 6:25 pm
ISP
-
ORD
12h 30m
1 stop
$343Southwest
Sat, May 9 - Tue, May 12
Frontier Logo
9:32 am - 11:57 pm
ORD
-
ISP
13h 25m
1 stop
Frontier Logo
5:43 pm - 11:36 pm
ISP
-
ORD
6h 53m
1 stop
$345Frontier
Sat, Apr 4 - Tue, Apr 7
Southwest Logo
12:15 pm - 11:20 pm
ORD
-
ISP
10h 05m
2 stops
Southwest Logo
6:30 am - 4:05 pm
ISP
-
ORD
10h 35m
2 stops
$348Southwest
Sat, May 9 - Tue, May 12
Frontier Logo
9:32 am - 11:57 pm
ORD
-
ISP
13h 25m
1 stop
Frontier Logo
5:43 pm - 11:36 pm
ISP
-
ORD
6h 53m
1 stop
$365Frontier
Sat, Apr 4 - Tue, Apr 7
Southwest Logo
3:20 pm - 11:40 pm
ORD
-
ISP
7h 20m
1 stop
Southwest Logo
6:25 am - 2:20 pm
ISP
-
ORD
8h 55m
1 stop
$387Southwest
Thu, Jul 16 - Tue, Jul 21
Southwest Logo
1:35 pm - 10:40 pm
ORD
-
ISP
8h 05m
1 stop
Southwest Logo
6:50 am - 2:20 pm
ISP
-
ORD
8h 30m
1 stop
$391Southwest
Tue, Apr 14 - Fri, Apr 17
Southwest Logo
3:20 pm - 11:40 pm
ORD
-
ISP
7h 20m
1 stop
Southwest Logo
2:55 pm - 11:55 pm
ISP
-
ORD
10h 00m
2 stops
$392Southwest
Thu, Jul 16 - Tue, Jul 21

Frontier flights from Chicago to Islip, New York

Our best Frontier deals on Chicago to Islip, New York flight tickets
Frontier
May 14
ORD10:25 amChicago O'Hare Intl
21h 48m
1 stop
ISP9:13 amIslip Long Island
May 17
ISP4:07 pmIslip Long Island
23h 10m
1 stop
ORD2:17 pmChicago O'Hare Intl
$215
Frontier
Apr 4
ORD9:32 amChicago O'Hare Intl
13h 25m
1 stop
ISP11:57 pmIslip Long Island
Apr 7
ISP5:43 pmIslip Long Island
6h 53m
1 stop
ORD11:36 pmChicago O'Hare Intl
$345
Frontier
Apr 4
ORD9:32 amChicago O'Hare Intl
13h 25m
1 stop
ISP11:57 pmIslip Long Island
Apr 7
ISP5:43 pmIslip Long Island
6h 53m
1 stop
ORD11:36 pmChicago O'Hare Intl
$365

Southwest flights from Chicago to Islip, New York

Our best Southwest deals on Chicago to Islip, New York flight tickets
Southwest
May 9
ORD12:15 pmChicago O'Hare Intl
9h 25m
1 stop
ISP10:40 pmIslip Long Island
May 12
ISP6:30 amIslip Long Island
10h 35m
2 stops
ORD4:05 pmChicago O'Hare Intl
$342
Southwest
May 9
ORD12:15 pmChicago O'Hare Intl
9h 25m
1 stop
ISP10:40 pmIslip Long Island
May 12
ISP6:55 amIslip Long Island
12h 30m
1 stop
ORD6:25 pmChicago O'Hare Intl
$343
Southwest
May 9
ORD12:15 pmChicago O'Hare Intl
10h 05m
2 stops
ISP11:20 pmIslip Long Island
May 12
ISP6:30 amIslip Long Island
10h 35m
2 stops
ORD4:05 pmChicago O'Hare Intl
$348

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 March 13, 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

Thu 5/14

10:25 am-9:13 am

1 stop21h 48m

Islip Long Island

Sun 5/17

4:07 pm-2:17 pm

1 stop23h 10m

$215

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Tue 4/14

11:25 am-11:10 am

2 stops22h 45m

Islip Long Island

Fri 4/17

4:07 pm-11:07 pm

1 stop8h 00m

$310

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 5/9

12:15 pm-10:40 pm

1 stop9h 25m

Islip Long Island

Tue 5/12

6:30 am-4:05 pm

2 stops10h 35m

$342

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 5/9

12:15 pm-10:40 pm

1 stop9h 25m

Islip Long Island

Tue 5/12

6:55 am-6:25 pm

1 stop12h 30m

$343

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 4/4

9:32 am-11:57 pm

1 stop13h 25m

Islip Long Island

Tue 4/7

5:43 pm-11:36 pm

1 stop6h 53m

$345

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 5/9

12:15 pm-11:20 pm

2 stops10h 05m

Islip Long Island

Tue 5/12

6:30 am-4:05 pm

2 stops10h 35m

$348

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 4/4

9:32 am-11:57 pm

1 stop13h 25m

Islip Long Island

Tue 4/7

5:43 pm-11:36 pm

1 stop6h 53m

$365
Quickest round-trip

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 7/16

3:20 pm-11:40 pm

1 stop7h 20m

Islip Long Island

Tue 7/21

6:25 am-2:20 pm

1 stop8h 55m

$387

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Tue 4/14

1:35 pm-10:40 pm

1 stop8h 05m

Islip Long Island

Fri 4/17

6:50 am-2:20 pm

1 stop8h 30m

$391

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 7/16

3:20 pm-11:40 pm

1 stop7h 20m

Islip Long Island

Tue 7/21

2:55 pm-11:55 pm

2 stops10h 00m

$392

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 is the most popular carrier 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 43% 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

5h 29m

Direct flights

None
The fastest flight from Chicago to Islip, New York takes 5h 29m
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

  • 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 5h 29m.

  • 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
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.

An easier way to manage your Islip, New York trip

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