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Cheap flights from Chicago to New York from $85

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 5/28. 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
5:11 pm - 10:05 am
ORD
-
ISP
15h 54m
1 stop
Frontier Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
$180Frontier
Thu, May 28 - Mon, Jun 1
Frontier Logo
6:00 am - 11:00 am
ORD
-
ISP
28h 00m
1 stop
Frontier Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
$236Frontier
Mon, May 4 - Fri, May 8
Multiple Airlines Logo
1:59 pm - 10:05 am
ORD
-
ISP
19h 06m
2 stops
Multiple Airlines Logo
6:02 pm - 10:14 pm
ISP
-
ORD
29h 12m
1 stop
$245Multiple Airlines
Tue, May 19 - Tue, May 26
Multiple Airlines Logo
1:50 pm - 10:05 am
ORD
-
ISP
19h 15m
2 stops
Multiple Airlines Logo
10:48 am - 10:14 pm
ISP
-
ORD
12h 26m
1 stop
$251Multiple Airlines
Fri, Jun 5 - Wed, Jun 10
Multiple Airlines Logo
2:10 pm - 11:00 am
ORD
-
ISP
19h 50m
2 stops
Multiple Airlines Logo
6:59 pm - 12:23 pm
ISP
-
ORD
18h 24m
1 stop
$256Multiple Airlines
Mon, May 4 - Fri, May 8
Frontier Logo
7:15 am - 10:05 am
ORD
-
ISP
25h 50m
2 stops
Frontier Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
$258Frontier
Tue, May 5 - Sat, May 9
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
$270Frontier
Thu, May 14 - Sun, May 17
Multiple Airlines Logo
3:55 pm - 10:05 am
ORD
-
ISP
17h 10m
1 stop
Multiple Airlines Logo
11:00 am - 10:14 pm
ISP
-
ORD
12h 14m
1 stop
$273Multiple Airlines
Tue, May 5 - Sat, May 9
Multiple Airlines Logo
8:30 am - 5:58 pm
ORD
-
ISP
8h 28m
1 stop
Multiple Airlines Logo
6:43 pm - 11:33 am
ISP
-
ORD
17h 50m
2 stops
$278Multiple Airlines
Sat, Jun 6 - Mon, Jun 8
Multiple Airlines Logo
10:49 am - 11:00 am
ORD
-
ISP
23h 11m
1 stop
Multiple Airlines Logo
6:59 pm - 12:23 pm
ISP
-
ORD
18h 24m
1 stop
$297Multiple Airlines
Mon, May 4 - Fri, May 8

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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 28
ORD5:11 pmChicago O'Hare Intl
15h 54m
1 stop
ISP10:05 amIslip Long Island
Jun 1
ISP11:00 amIslip Long Island
13h 13m
1 stop
ORD11:13 pmChicago O'Hare Intl
$180
Frontier
May 4
ORD6:00 amChicago O'Hare Intl
28h 00m
1 stop
ISP11:00 amIslip Long Island
May 8
ISP11:00 amIslip Long Island
13h 13m
1 stop
ORD11:13 pmChicago O'Hare Intl
$236
Frontier
May 5
ORD7:15 amChicago O'Hare Intl
25h 50m
2 stops
ISP10:05 amIslip Long Island
May 9
ISP11:00 amIslip Long Island
13h 13m
1 stop
ORD11:13 pmChicago O'Hare Intl
$258

Southwest flights from Chicago to Islip, New York

Our best Southwest deals on Chicago to Islip, New York flight tickets
Southwest
May 22
ORD2:40 pmChicago O'Hare Intl
7h 50m
2 stops
ISP11:30 pmIslip Long Island
May 26
ISP2:30 pmIslip Long Island
8h 25m
2 stops
ORD9:55 pmChicago O'Hare Intl
$366
Southwest
May 26
ORD5:55 amChicago O'Hare Intl
11h 35m
2 stops
ISP6:30 pmIslip Long Island
May 28
ISP6:50 amIslip Long Island
8h 30m
1 stop
ORD2:20 pmChicago O'Hare Intl
$396
Southwest
May 26
ORD5:55 amChicago O'Hare Intl
11h 35m
2 stops
ISP6:30 pmIslip Long Island
May 28
ISP6:00 amIslip Long Island
9h 20m
2 stops
ORD2:20 pmChicago O'Hare Intl
$401

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 23, 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 5/28

5:11 pm-10:05 am

1 stop15h 54m

Islip Long Island

Mon 6/1

11:00 am-11:13 pm

1 stop13h 13m

$180

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 5/4

6:00 am-11:00 am

1 stop28h 00m

Islip Long Island

Fri 5/8

11:00 am-11:13 pm

1 stop13h 13m

$236

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Tue 5/19

1:59 pm-10:05 am

2 stops19h 06m

Islip Long Island

Tue 5/26

6:02 pm-10:14 pm

1 stop29h 12m

$245

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Fri 6/5

1:50 pm-10:05 am

2 stops19h 15m

Islip Long Island

Wed 6/10

10:48 am-10:14 pm

1 stop12h 26m

$251

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 5/4

2:10 pm-11:00 am

2 stops19h 50m

Islip Long Island

Fri 5/8

6:59 pm-12:23 pm

1 stop18h 24m

$256

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Tue 5/5

7:15 am-10:05 am

2 stops25h 50m

Islip Long Island

Sat 5/9

11:00 am-11:13 pm

1 stop13h 13m

$258

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Thu 5/14

5:30 pm-10:05 am

1 stop15h 35m

Islip Long Island

Sun 5/17

11:12 am-11:13 pm

1 stop13h 01m

$270

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Tue 5/5

3:55 pm-10:05 am

1 stop17h 10m

Islip Long Island

Sat 5/9

11:00 am-10:14 pm

1 stop12h 14m

$273
Quickest round-trip

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Sat 6/6

8:30 am-5:58 pm

1 stop8h 28m

Islip Long Island

Mon 6/8

6:43 pm-11:33 am

2 stops17h 50m

$278

ChicagoIslip

ORD - ISP

ORDISP

Chicago O'Hare Intl

Mon 5/4

10:49 am-11:00 am

1 stop23h 11m

Islip Long Island

Fri 5/8

6:59 pm-12:23 pm

1 stop18h 24m

$297

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

12h 15m

Direct flights

None
The fastest flight from Chicago to Islip, New York takes 12h 15m
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 12h 15m.

  • 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.

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