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Cheap flights from Chicago to New York from $96

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 4/5. 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
6:00 am - 9:28 am
ORD
-
ISP
26h 28m
1 stop
Frontier Logo
8:31 pm - 11:58 pm
ISP
-
ORD
28h 27m
1 stop
$162Frontier
Sun, Apr 26 - Sun, May 3
Frontier Logo
5:25 am - 1:38 am
ORD
-
ISP
19h 13m
1 stop
Frontier Logo
3:55 pm - 11:36 pm
ISP
-
ORD
8h 41m
1 stop
$201Frontier
Sun, Apr 5 - Thu, Apr 9
Frontier Logo
5:25 am - 1:38 am
ORD
-
ISP
19h 13m
1 stop
Frontier Logo
3:55 pm - 11:36 pm
ISP
-
ORD
8h 41m
1 stop
$203Frontier
Sun, Apr 5 - Thu, Apr 9
Frontier Logo
5:25 am - 1:26 am
ORD
-
ISP
19h 01m
1 stop
Frontier Logo
8:31 pm - 11:58 pm
ISP
-
ORD
28h 27m
1 stop
$222Frontier
Thu, Apr 9 - Thu, Apr 16
Frontier Logo
5:25 am - 12:23 am
ORD
-
ISP
17h 58m
1 stop
Frontier Logo
4:01 pm - 11:36 pm
ISP
-
ORD
8h 35m
1 stop
$235Frontier
Mon, Apr 6 - Fri, Apr 10
Frontier Logo
5:30 pm - 10:05 am
ORD
-
ISP
15h 35m
1 stop
Frontier Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
$249Frontier
Thu, May 14 - Mon, May 18
Multiple Airlines Logo
11:51 am - 10:05 am
ORD
-
ISP
21h 14m
2 stops
Multiple Airlines Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
$254Multiple Airlines
Thu, May 14 - Mon, May 18
Frontier Logo
5:25 am - 1:26 am
ORD
-
ISP
19h 01m
1 stop
Frontier Logo
4:01 pm - 11:36 pm
ISP
-
ORD
8h 35m
1 stop
$256Frontier
Thu, Apr 9 - Mon, Apr 13
Frontier Logo
4:21 pm - 11:13 am
ORD
-
ISP
17h 52m
1 stop
Frontier Logo
5:43 pm - 11:36 pm
ISP
-
ORD
6h 53m
1 stop
$260Frontier
Sat, Apr 4 - Tue, Apr 7
Frontier Logo
8:45 am - 6:39 pm
ORD
-
ISP
8h 54m
1 stop
Frontier Logo
5:28 pm - 11:36 pm
ISP
-
ORD
7h 08m
1 stop
$270Frontier
Sat, Apr 4 - Wed, Apr 8

Southwest flights from Chicago to Islip, New York

Our best Southwest deals on Chicago to Islip, New York flight tickets
Southwest
May 1
ORD2:40 pmChicago O'Hare Intl
7h 50m
2 stops
ISP11:30 pmIslip Long Island
May 5
ISP6:30 amIslip Long Island
10h 35m
2 stops
ORD4:05 pmChicago O'Hare Intl
$328
Southwest
May 1
ORD7:35 pmChicago O'Hare Intl
12h 45m
1 stop
ISP9:20 amIslip Long Island
May 5
ISP6:30 amIslip Long Island
10h 35m
2 stops
ORD4:05 pmChicago O'Hare Intl
$329
Southwest
May 14
ORD2:40 pmChicago O'Hare Intl
7h 50m
2 stops
ISP11:30 pmIslip Long Island
May 18
ISP6:00 amIslip Long Island
7h 50m
2 stops
ORD12:50 pmChicago O'Hare Intl
$373

Frontier flights from Chicago to Islip, New York

Our best Frontier deals on Chicago to Islip, New York flight tickets
Frontier
Apr 26
ORD6:00 amChicago O'Hare Intl
26h 28m
1 stop
ISP9:28 amIslip Long Island
May 3
ISP8:31 pmIslip Long Island
28h 27m
1 stop
ORD11:58 pmChicago O'Hare Intl
$162
Frontier
Apr 5
ORD5:25 amChicago O'Hare Intl
19h 13m
1 stop
ISP1:38 amIslip Long Island
Apr 9
ISP3:55 pmIslip Long Island
8h 41m
1 stop
ORD11:36 pmChicago O'Hare Intl
$201
Frontier
Apr 5
ORD5:25 amChicago O'Hare Intl
19h 13m
1 stop
ISP1:38 amIslip Long Island
Apr 9
ISP3:55 pmIslip Long Island
8h 41m
1 stop
ORD11:36 pmChicago O'Hare Intl
$203

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 25, 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 4/26

6:00 am-9:28 am

1 stop26h 28m

Islip Long Island

Sun 5/3

8:31 pm-11:58 pm

1 stop28h 27m

$162

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sun 4/5

5:25 am-1:38 am

1 stop19h 13m

Islip Long Island

Thu 4/9

3:55 pm-11:36 pm

1 stop8h 41m

$201

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sun 4/5

5:25 am-1:38 am

1 stop19h 13m

Islip Long Island

Thu 4/9

3:55 pm-11:36 pm

1 stop8h 41m

$203

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 4/9

5:25 am-1:26 am

1 stop19h 01m

Islip Long Island

Thu 4/16

8:31 pm-11:58 pm

1 stop28h 27m

$222

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 4/6

5:25 am-12:23 am

1 stop17h 58m

Islip Long Island

Fri 4/10

4:01 pm-11:36 pm

1 stop8h 35m

$235

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 5/14

5:30 pm-10:05 am

1 stop15h 35m

Islip Long Island

Mon 5/18

11:00 am-11:13 pm

1 stop13h 13m

$249

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 5/14

11:51 am-10:05 am

2 stops21h 14m

Islip Long Island

Mon 5/18

11:00 am-11:13 pm

1 stop13h 13m

$254

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 4/9

5:25 am-1:26 am

1 stop19h 01m

Islip Long Island

Mon 4/13

4:01 pm-11:36 pm

1 stop8h 35m

$256

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 4/4

4:21 pm-11:13 am

1 stop17h 52m

Islip Long Island

Tue 4/7

5:43 pm-11:36 pm

1 stop6h 53m

$260
Quickest round-trip

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 4/4

8:45 am-6:39 pm

1 stop8h 54m

Islip Long Island

Wed 4/8

5:28 pm-11:36 pm

1 stop7h 08m

$270

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 44% 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 43m

Direct flights

None
The fastest flight from Chicago to Islip, New York takes 7h 43m
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 7h 43m.

  • 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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