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Cheap flights from Islip, New York to Chicago from $129

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Islip, New York to Chicago departing on 9/10. 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

Find the cheapest flights from Islip, New York to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
7:09 pm - 1:20 pm
ISP
-
ORD
19h 11m
1 stop
Frontier Logo
7:44 pm - 9:53 am
ORD
-
ISP
13h 09m
1 stop
$258Frontier
Thu, Aug 20 - Thu, Aug 27
Frontier Logo
10:57 am - 11:08 pm
ISP
-
ORD
13h 11m
1 stop
Frontier Logo
6:05 am - 6:14 pm
ORD
-
ISP
11h 09m
1 stop
$263Frontier
Fri, Aug 21 - Mon, Aug 24
Frontier Logo
10:57 am - 11:08 pm
ISP
-
ORD
13h 11m
1 stop
Frontier Logo
7:44 pm - 9:53 am
ORD
-
ISP
13h 09m
1 stop
$268Frontier
Fri, Aug 21 - Sun, Aug 23
Frontier Logo
10:57 am - 11:08 pm
ISP
-
ORD
13h 11m
1 stop
Frontier Logo
5:59 pm - 6:14 pm
ORD
-
ISP
23h 15m
1 stop
$270Frontier
Thu, Aug 20 - Wed, Aug 26
Frontier Logo
10:57 am - 11:08 pm
ISP
-
ORD
13h 11m
1 stop
Frontier Logo
7:44 pm - 9:53 am
ORD
-
ISP
13h 09m
1 stop
$273Frontier
Tue, Sep 1 - Wed, Sep 2
Frontier Logo
7:09 pm - 11:08 pm
ISP
-
ORD
28h 59m
1 stop
Frontier Logo
5:59 pm - 6:14 pm
ORD
-
ISP
23h 15m
1 stop
$276Frontier
Mon, Aug 24 - Wed, Aug 26
Frontier Logo
10:57 am - 11:08 pm
ISP
-
ORD
13h 11m
1 stop
Frontier Logo
7:44 pm - 9:53 am
ORD
-
ISP
13h 09m
1 stop
$278Frontier
Thu, Aug 20 - Sun, Aug 23
Frontier Logo
7:09 pm - 11:08 pm
ISP
-
ORD
28h 59m
1 stop
Frontier Logo
5:59 pm - 6:14 pm
ORD
-
ISP
23h 15m
1 stop
$281Frontier
Mon, Aug 24 - Wed, Aug 26
Frontier Logo
10:57 am - 11:10 pm
ISP
-
ORD
13h 13m
1 stop
Frontier Logo
5:13 pm - 9:53 am
ORD
-
ISP
15h 40m
1 stop
$290Frontier
Wed, Aug 5 - Sun, Aug 9
Frontier Logo
10:57 am - 11:10 pm
ISP
-
ORD
13h 13m
1 stop
Frontier Logo
5:13 pm - 9:53 am
ORD
-
ISP
15h 40m
1 stop
$297Frontier
Fri, Jul 31 - Tue, Aug 4

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Frontier flights from Islip, New York to Chicago O'Hare Intl Airport

Our best Frontier deals on Islip, New York to Chicago O'Hare Intl Airport flight tickets
Frontier
Aug 20
ISP7:09 pmIslip Long Island
19h 11m
1 stop
ORD1:20 pmChicago O'Hare Intl
Aug 27
ORD7:44 pmChicago O'Hare Intl
13h 09m
1 stop
ISP9:53 amIslip Long Island
$258
Frontier
Aug 21
ISP10:57 amIslip Long Island
13h 11m
1 stop
ORD11:08 pmChicago O'Hare Intl
Aug 24
ORD6:05 amChicago O'Hare Intl
11h 09m
1 stop
ISP6:14 pmIslip Long Island
$263
Frontier
Aug 21
ISP10:57 amIslip Long Island
13h 11m
1 stop
ORD11:08 pmChicago O'Hare Intl
Aug 23
ORD7:44 pmChicago O'Hare Intl
13h 09m
1 stop
ISP9:53 amIslip Long Island
$268

JetBlue flights from Islip, New York to Chicago O'Hare Intl Airport

Our best JetBlue deals on Islip, New York to Chicago O'Hare Intl Airport flight tickets
JetBlue
Sep 15
ISP7:00 amIslip Long Island
8h 01m
1 stop
ORD2:01 pmChicago O'Hare Intl
Sep 17
ORD3:00 pmChicago O'Hare Intl
7h 22m
1 stop
ISP11:22 pmIslip Long Island
$415
JetBlue
Sep 8
ISP6:00 amIslip Long Island
8h 39m
1 stop
ORD1:39 pmChicago O'Hare Intl
Sep 12
ORD3:00 pmChicago O'Hare Intl
7h 22m
1 stop
ISP11:22 pmIslip Long Island
$420
JetBlue
Sep 27
ISP7:00 amIslip Long Island
8h 01m
1 stop
ORD2:01 pmChicago O'Hare Intl
Oct 2
ORD3:00 pmChicago O'Hare Intl
7h 22m
1 stop
ISP11:22 pmIslip Long Island
$494

momondo Fare Finder

 
Customize your flight search to find flights from Islip, New York to Chicago O'Hare Intl Airport 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 July 9, 2026.
Use the filters below to find and compare flights from Islip, New York to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 8/20

7:09 pm-1:20 pm

1 stop19h 11m

Chicago O'Hare Intl

Thu 8/27

7:44 pm-9:53 am

1 stop13h 09m

$258
Quickest round-trip

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 8/21

10:57 am-11:08 pm

1 stop13h 11m

Chicago O'Hare Intl

Mon 8/24

6:05 am-6:14 pm

1 stop11h 09m

$263

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 8/21

10:57 am-11:08 pm

1 stop13h 11m

Chicago O'Hare Intl

Sun 8/23

7:44 pm-9:53 am

1 stop13h 09m

$268

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 8/20

10:57 am-11:08 pm

1 stop13h 11m

Chicago O'Hare Intl

Wed 8/26

5:59 pm-6:14 pm

1 stop23h 15m

$270

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 9/1

10:57 am-11:08 pm

1 stop13h 11m

Chicago O'Hare Intl

Wed 9/2

7:44 pm-9:53 am

1 stop13h 09m

$273

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 8/24

7:09 pm-11:08 pm

1 stop28h 59m

Chicago O'Hare Intl

Wed 8/26

5:59 pm-6:14 pm

1 stop23h 15m

$276

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 8/20

10:57 am-11:08 pm

1 stop13h 11m

Chicago O'Hare Intl

Sun 8/23

7:44 pm-9:53 am

1 stop13h 09m

$278

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 8/24

7:09 pm-11:08 pm

1 stop28h 59m

Chicago O'Hare Intl

Wed 8/26

5:59 pm-6:14 pm

1 stop23h 15m

$281

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 8/5

10:57 am-11:10 pm

1 stop13h 13m

Chicago O'Hare Intl

Sun 8/9

5:13 pm-9:53 am

1 stop15h 40m

$290

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 7/31

10:57 am-11:10 pm

1 stop13h 13m

Chicago O'Hare Intl

Tue 8/4

5:13 pm-9:53 am

1 stop15h 40m

$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 Chicago from

How to get the cheapest flight ticket from Islip, New York to Chicago O'Hare Intl Airport

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 day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Saturday when prices can be found for as low as $320. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Islip, New York because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $391.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Islip, New York in the evening is the least expensive time of day to depart. momondo users have found prices as low as $308 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $371. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from Islip, New York to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Islip, New York to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Islip, New York to Chicago O'Hare Intl Airport (ISP to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Islip, New York to Chicago O'Hare Intl Airport

Fastest flight time

8h 01m

Direct flights

None
The fastest flight from Islip, New York to Chicago O'Hare Intl Airport takes 8h 01m
There are no direct flights from Islip, New York to Chicago O'Hare Intl Airport. There are no popular flight routes from Islip, New York to Chicago O'Hare Intl Airport.
Search flight deals

Frequently asked questions about flying from Islip, New York to Chicago O'Hare Intl Airport

  • How far is Islip Long Island to Chicago O'Hare Intl by plane?

    Chicago O'Hare Intl is 765.5 mi away from Islip Long Island. In terms of flight time, this usually takes a little over 8h 01m.

  • When did momondo last update prices for flights from Islip Long Island Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Islip Long Island Airport to Chicago O'Hare Intl Airport are updated daily.

  • How old do you have to be to fly from Islip Long Island Airport to Chicago O'Hare Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Islip Long Island Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
Orland Park
Oak Brook
New Buffalo
Joliet
Kenosha
Hammond
Aurora
Racine
Janesville
Elgin
Evanston
South Holland

Why use momondo?

Why should I use momondo to find a flight deal from Islip to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Islip.

Can I find flights from Islip to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Islip to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Islip to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Islip. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Islip to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Islip to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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