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Cheap flights from Islip, New York to Chicago from $109

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.
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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
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
Frontier Logo
5:11 pm - 5:17 pm
ORD
-
ISP
23h 06m
1 stop
$261Frontier
Thu, May 28 - Mon, Jun 1
Frontier Logo
4:13 pm - 11:55 pm
ISP
-
ORD
8h 42m
1 stop
Frontier Logo
4:49 pm - 9:33 am
ORD
-
ISP
15h 44m
1 stop
$266Frontier
Sat, Oct 3 - Mon, Oct 5
Frontier Logo
4:13 pm - 11:55 pm
ISP
-
ORD
8h 42m
1 stop
Frontier Logo
9:26 am - 9:33 am
ORD
-
ISP
23h 07m
1 stop
$280Frontier
Thu, Sep 24 - Sun, Sep 27
Frontier Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
Frontier Logo
5:11 pm - 5:17 pm
ORD
-
ISP
23h 06m
1 stop
$292Frontier
Sat, May 30 - Mon, Jun 1
Frontier Logo
4:13 pm - 8:21 am
ISP
-
ORD
17h 08m
1 stop
Frontier Logo
4:49 pm - 9:33 am
ORD
-
ISP
15h 44m
1 stop
$301Frontier
Sat, Sep 26 - Mon, Sep 28
Frontier Logo
6:02 pm - 7:29 pm
ISP
-
ORD
26h 27m
2 stops
Frontier Logo
1:29 pm - 10:15 am
ORD
-
ISP
19h 46m
2 stops
$314Frontier
Tue, Jun 2 - Fri, Jun 5
Frontier Logo
10:48 am - 11:14 pm
ISP
-
ORD
13h 26m
1 stop
Frontier Logo
5:30 pm - 10:03 am
ORD
-
ISP
15h 33m
1 stop
$326Frontier
Sun, Aug 30 - Fri, Sep 4
Frontier Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
Frontier Logo
5:11 pm - 10:15 am
ORD
-
ISP
16h 04m
1 stop
$339Frontier
Mon, Jun 1 - Fri, Jun 5
Frontier Logo
11:00 am - 11:13 pm
ISP
-
ORD
13h 13m
1 stop
Frontier Logo
6:55 am - 10:05 am
ORD
-
ISP
26h 10m
2 stops
$349Frontier
Thu, Jun 4 - Sun, Jun 7
Multiple Airlines Logo
4:13 pm - 11:55 pm
ISP
-
ORD
8h 42m
1 stop
Multiple Airlines Logo
4:49 pm - 12:58 pm
ORD
-
ISP
19h 09m
2 stops
$350Multiple Airlines
Sat, Sep 26 - Mon, Sep 28

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

Our best Southwest deals on Islip, New York to Chicago O'Hare Intl Airport flight tickets
Southwest
May 30
ISP5:30 amIslip Long Island
11h 00m
2 stops
ORD3:30 pmChicago O'Hare Intl
Jun 1
ORD3:05 pmChicago O'Hare Intl
6h 25m
1 stop
ISP10:30 pmIslip Long Island
$462
Southwest
May 30
ISP6:00 amIslip Long Island
10h 30m
2 stops
ORD3:30 pmChicago O'Hare Intl
Jun 1
ORD7:35 pmChicago O'Hare Intl
15h 20m
2 stops
ISP11:55 amIslip Long Island
$473
Southwest
May 29
ISP6:50 amIslip Long Island
8h 30m
1 stop
ORD2:20 pmChicago O'Hare Intl
May 31
ORD1:35 pmChicago O'Hare Intl
9h 10m
1 stop
ISP11:45 pmIslip Long Island
$487

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
May 28
ISP11:00 amIslip Long Island
13h 13m
1 stop
ORD11:13 pmChicago O'Hare Intl
Jun 1
ORD5:11 pmChicago O'Hare Intl
23h 06m
1 stop
ISP5:17 pmIslip Long Island
$261
Frontier
Oct 3
ISP4:13 pmIslip Long Island
8h 42m
1 stop
ORD11:55 pmChicago O'Hare Intl
Oct 5
ORD4:49 pmChicago O'Hare Intl
15h 44m
1 stop
ISP9:33 amIslip Long Island
$266
Frontier
Sep 24
ISP4:13 pmIslip Long Island
8h 42m
1 stop
ORD11:55 pmChicago O'Hare Intl
Sep 27
ORD9:26 amChicago O'Hare Intl
23h 07m
1 stop
ISP9:33 amIslip Long Island
$280

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 May 16, 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 5/28

11:00 am-11:13 pm

1 stop13h 13m

Chicago O'Hare Intl

Mon 6/1

5:11 pm-5:17 pm

1 stop23h 06m

$261
Quickest round-trip

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 10/3

4:13 pm-11:55 pm

1 stop8h 42m

Chicago O'Hare Intl

Mon 10/5

4:49 pm-9:33 am

1 stop15h 44m

$266

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 9/24

4:13 pm-11:55 pm

1 stop8h 42m

Chicago O'Hare Intl

Sun 9/27

9:26 am-9:33 am

1 stop23h 07m

$280

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 5/30

11:00 am-11:13 pm

1 stop13h 13m

Chicago O'Hare Intl

Mon 6/1

5:11 pm-5:17 pm

1 stop23h 06m

$292

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 9/26

4:13 pm-8:21 am

1 stop17h 08m

Chicago O'Hare Intl

Mon 9/28

4:49 pm-9:33 am

1 stop15h 44m

$301

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 6/2

6:02 pm-7:29 pm

2 stops26h 27m

Chicago O'Hare Intl

Fri 6/5

1:29 pm-10:15 am

2 stops19h 46m

$314

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 8/30

10:48 am-11:14 pm

1 stop13h 26m

Chicago O'Hare Intl

Fri 9/4

5:30 pm-10:03 am

1 stop15h 33m

$326

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 6/1

11:00 am-11:13 pm

1 stop13h 13m

Chicago O'Hare Intl

Fri 6/5

5:11 pm-10:15 am

1 stop16h 04m

$339

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 6/4

11:00 am-11:13 pm

1 stop13h 13m

Chicago O'Hare Intl

Sun 6/7

6:55 am-10:05 am

2 stops26h 10m

$349

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 9/26

4:13 pm-11:55 pm

1 stop8h 42m

Chicago O'Hare Intl

Mon 9/28

4:49 pm-12:58 pm

2 stops19h 09m

$350

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 $292. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday 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 $368.

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 $278 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $364. 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

7h 44m

Direct flights

None
The fastest flight from Islip, New York to Chicago O'Hare Intl Airport takes 7h 44m
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 7h 44m.

  • 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
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Rosemont
Naperville
Orland Park
New Buffalo
Oak Brook
Kenosha
Joliet
Aurora
Racine
Janesville
Hammond
Evanston
Elgin
Tinley Park

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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