Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Chicago to New York from $171

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago to New York

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:00 am - 11:45 amMDW  Chicago Midway-ISP Islip Long Island
4h 45m1 stop Baltimore/Washington
Southwest Logo
4:05 pm - 9:30 pmISP  Islip Long Island-MDW Chicago Midway
6h 25m1 stop Baltimore/Washington
$378Southwest
Wed, Dec 9 - Wed, Dec 9
Southwest Logo
6:00 am - 11:45 amMDW  Chicago Midway-ISP Islip Long Island
4h 45m1 stop Baltimore/Washington
Southwest Logo
4:05 pm - 10:45 pmISP  Islip Long Island-MDW Chicago Midway
7h 40m2 stops Baltimore/Washington Nashville Intl
$383Southwest
Wed, Dec 9 - Wed, Dec 9
Southwest Logo
12:55 pm - 10:50 pmMDW  Chicago Midway-ISP Islip Long Island
8h 55m2 stops Greater Rochester Intl Orlando
Southwest Logo
9:25 am - 4:30 pmISP  Islip Long Island-MDW Chicago Midway
8h 05m1 stop Tampa
$552Southwest
Fri, Nov 20 - Tue, Nov 24
Southwest Logo
12:55 pm - 10:50 pmMDW  Chicago Midway-ISP Islip Long Island
8h 55m2 stops Greater Rochester Intl Orlando
Southwest Logo
6:05 am - 1:45 pmISP  Islip Long Island-MDW Chicago Midway
8h 40m2 stops Baltimore/Washington Hartford Bradley Intl
$583Southwest
Fri, Nov 20 - Tue, Nov 24
Southwest Logo
5:10 am - 12:45 pmMDW  Chicago Midway-ISP Islip Long Island
6h 35m1 stop Orlando
Southwest Logo
9:25 am - 4:30 pmISP  Islip Long Island-MDW Chicago Midway
8h 05m1 stop Tampa
$597Southwest
Fri, Nov 20 - Tue, Nov 24
Frontier Logo
8:35 pm - 10:31 amMDW  Chicago Midway-ISP Islip Long Island
12h 56m1 stop Orlando
Frontier Logo
11:26 am - 7:30 pmISP  Islip Long Island-MDW Chicago Midway
9h 04m1 stop Orlando
$674Frontier
Sun, Dec 20 - Wed, Dec 23
Frontier Logo
8:42 pm - 3:45 pmMDW  Chicago Midway-ISP Islip Long Island
18h 03m1 stop Orlando
Frontier Logo
4:43 pm - 7:47 pmISP  Islip Long Island-MDW Chicago Midway
28h 04m1 stop Orlando
$740Frontier
Tue, Nov 24 - Sat, Nov 28
Frontier Logo
8:35 pm - 10:31 amMDW  Chicago Midway-ISP Islip Long Island
12h 56m1 stop Orlando
Frontier Logo
11:26 am - 12:01 amISP  Islip Long Island-MDW Chicago Midway
13h 35m2 stops Orlando Atlanta Hartsfield-Jackson
$763Frontier
Sun, Dec 20 - Wed, Dec 23
Southwest Logo
7:45 am - 5:20 pmMDW  Chicago Midway-ISP Islip Long Island
8h 35m2 stops Birmingham Tampa
Southwest Logo
5:30 am - 8:55 amISP  Islip Long Island-MDW Chicago Midway
4h 25m1 stop Baltimore/Washington
$768Southwest
Tue, Nov 24 - Sat, Nov 28
Southwest Logo
7:45 am - 5:20 pmMDW  Chicago Midway-ISP Islip Long Island
8h 35m2 stops Birmingham Tampa
Southwest Logo
5:30 am - 12:00 pmISP  Islip Long Island-MDW Chicago Midway
7h 30m2 stops Baltimore/Washington Lambert-St Louis
$840Southwest
Tue, Nov 24 - Sat, Nov 28

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Southwest flights from Chicago to Islip, New York

Our best Southwest deals on Chicago to Islip, New York flight tickets
Southwest
Dec 9
MDW6:00 amChicago Midway
4h 45m
1 stop
ISP11:45 amIslip Long Island
Dec 9
ISP4:05 pmIslip Long Island
6h 25m
1 stop
MDW9:30 pmChicago Midway
$378
Southwest
Dec 9
MDW6:00 amChicago Midway
4h 45m
1 stop
ISP11:45 amIslip Long Island
Dec 9
ISP4:05 pmIslip Long Island
7h 40m
2 stops
MDW10:45 pmChicago Midway
$383
Southwest
Nov 20
MDW12:55 pmChicago Midway
8h 55m
2 stops
ISP10:50 pmIslip Long Island
Nov 24
ISP9:25 amIslip Long Island
8h 05m
1 stop
MDW4:30 pmChicago Midway
$552

Frontier flights from Chicago to Islip, New York

Our best Frontier deals on Chicago to Islip, New York flight tickets
Frontier
Dec 20
MDW8:35 pmChicago Midway
12h 56m
1 stop
ISP10:31 amIslip Long Island
Dec 23
ISP11:26 amIslip Long Island
9h 04m
1 stop
MDW7:30 pmChicago Midway
$674
Frontier
Nov 24
MDW8:42 pmChicago Midway
18h 03m
1 stop
ISP3:45 pmIslip Long Island
Nov 28
ISP4:43 pmIslip Long Island
28h 04m
1 stop
MDW7:47 pmChicago Midway
$740
Frontier
Dec 20
MDW8:35 pmChicago Midway
12h 56m
1 stop
ISP10:31 amIslip Long Island
Dec 23
ISP11:26 amIslip Long Island
13h 35m
2 stops
MDW12:01 amChicago Midway
$763

momondo Fare Finder

 
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
Quickest round-trip

ChicagoIslip

MDW Chicago Midway - ISP Islip Long Island

MDWISP

Chicago Midway

Wed 12/9

6:00 am-11:45 am

1 stop4h 45m

Islip Long Island

Wed 12/9

4:05 pm-9:30 pm

1 stop6h 25m

$378

ChicagoIslip

MDW Chicago Midway - ISP Islip Long Island

MDWISP

Chicago Midway

Wed 12/9

6:00 am-11:45 am

1 stop4h 45m

Islip Long Island

Wed 12/9

4:05 pm-10:45 pm

2 stops7h 40m

$383

ChicagoIslip

MDW Chicago Midway - ISP Islip Long Island

MDWISP

Chicago Midway

Fri 11/20

12:55 pm-10:50 pm

2 stops8h 55m

Islip Long Island

Tue 11/24

9:25 am-4:30 pm

1 stop8h 05m

$552

ChicagoIslip

MDW Chicago Midway - ISP Islip Long Island

MDWISP

Chicago Midway

Fri 11/20

12:55 pm-10:50 pm

2 stops8h 55m

Islip Long Island

Tue 11/24

6:05 am-1:45 pm

2 stops8h 40m

$583

ChicagoIslip

MDW Chicago Midway - ISP Islip Long Island

MDWISP

Chicago Midway

Fri 11/20

5:10 am-12:45 pm

1 stop6h 35m

Islip Long Island

Tue 11/24

9:25 am-4:30 pm

1 stop8h 05m

$597

ChicagoIslip

MDW Chicago Midway - ISP Islip Long Island

MDWISP

Chicago Midway

Sun 12/20

8:35 pm-10:31 am

1 stop12h 56m

Islip Long Island

Wed 12/23

11:26 am-7:30 pm

1 stop9h 04m

$674

ChicagoIslip

MDW Chicago Midway - ISP Islip Long Island

MDWISP

Chicago Midway

Tue 11/24

8:42 pm-3:45 pm

1 stop18h 03m

Islip Long Island

Sat 11/28

4:43 pm-7:47 pm

1 stop28h 04m

$740

ChicagoIslip

MDW Chicago Midway - ISP Islip Long Island

MDWISP

Chicago Midway

Sun 12/20

8:35 pm-10:31 am

1 stop12h 56m

Islip Long Island

Wed 12/23

11:26 am-12:01 am

2 stops13h 35m

$763

ChicagoIslip

MDW Chicago Midway - ISP Islip Long Island

MDWISP

Chicago Midway

Tue 11/24

7:45 am-5:20 pm

2 stops8h 35m

Islip Long Island

Sat 11/28

5:30 am-8:55 am

1 stop4h 25m

$768

ChicagoIslip

MDW Chicago Midway - ISP Islip Long Island

MDWISP

Chicago Midway

Tue 11/24

7:45 am-5:20 pm

2 stops8h 35m

Islip Long Island

Sat 11/28

5:30 am-12:00 pm

2 stops7h 30m

$840

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

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 Delta 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 59% of people opting to fly with this airline when traveling to Islip, New York. Keep in mind that there are 6 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

Best Price Found

$171

Fastest flight time

9h 05m

Direct flights

None
The best one-way flight to Islip, New York from Chicago in the past 72 hours is $171. The best round-trip flight deal from Chicago to Islip, New York found on momondo in the last 72 hours is $378.
The fastest flight from Chicago to Islip, New York takes 9h 05m
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 9h 05m.

  • 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.

Traveling to a place near New York?

Book flights to New York if you plan to visit one of these locations
Montauk
Riverhead
Southampton
Amagansett
Sag Harbor

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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 12/9
Wed 12/16
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States