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Cheap flights from Islip, New York to Chicago from $64

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 3/4. 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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0 bags

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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.
Multiple Airlines Logo
8:00 am - 5:52 pm
ISP
-
ORD
10h 52m1 stop
Multiple Airlines Logo
10:48 am - 10:46 pm
ORD
-
ISP
10h 58m1 stop
$136Multiple Airlines
Tue, Jan 13 - Wed, Jan 14
Multiple Airlines Logo
8:00 am - 5:52 pm
ISP
-
ORD
10h 52m1 stop
Multiple Airlines Logo
5:15 am - 10:46 pm
ORD
-
ISP
16h 31m2 stops
$142Multiple Airlines
Tue, Jan 13 - Wed, Jan 14
Frontier Logo
7:33 pm - 4:35 pm
ISP
-
ORD
22h 02m1 stop
Frontier Logo
11:45 am - 8:47 pm
ORD
-
ISP
8h 02m1 stop
$143Frontier
Fri, Jan 23 - Fri, Jan 30
Multiple Airlines Logo
12:00 pm - 1:13 pm
ISP
-
ORD
26h 13m1 stop
Multiple Airlines Logo
7:21 pm - 6:55 pm
ORD
-
ISP
22h 34m1 stop
$164Multiple Airlines
Tue, Jan 20 - Tue, Jan 27
Multiple Airlines Logo
7:33 pm - 4:35 pm
ISP
-
ORD
22h 02m1 stop
Multiple Airlines Logo
8:43 pm - 8:40 am
ORD
-
ISP
34h 57m2 stops
$171Multiple Airlines
Fri, Jan 23 - Fri, Jan 30
Multiple Airlines Logo
12:00 pm - 11:22 am
ISP
-
ORD
24h 22m2 stops
Multiple Airlines Logo
7:21 pm - 6:55 pm
ORD
-
ISP
22h 34m1 stop
$177Multiple Airlines
Tue, Jan 20 - Tue, Jan 27
Multiple Airlines Logo
8:00 am - 11:46 pm
ISP
-
ORD
16h 46m2 stops
Multiple Airlines Logo
5:15 am - 10:46 pm
ORD
-
ISP
16h 31m2 stops
$180Multiple Airlines
Tue, Jan 13 - Wed, Jan 14
Frontier Logo
7:43 pm - 10:35 am
ISP
-
ORD
15h 52m1 stop
Frontier Logo
3:55 pm - 6:38 pm
ORD
-
ISP
25h 43m1 stop
$184Frontier
Thu, Jan 22 - Thu, Jan 29
Frontier Logo
7:43 pm - 10:35 am
ISP
-
ORD
15h 52m1 stop
Frontier Logo
12:21 pm - 6:48 pm
ORD
-
ISP
29h 27m1 stop
$198Frontier
Thu, Jan 22 - Sun, Jan 25
Frontier Logo
5:07 pm - 9:40 pm
ISP
-
ORD
29h 33m1 stop
Frontier Logo
2:13 pm - 1:32 pm
ORD
-
ISP
22h 19m1 stop
$217Frontier
Thu, Feb 26 - Sun, Mar 1

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
Jan 23
ISP7:33 pmIslip Long Island
22h 02m
1 stop
ORD4:35 pmChicago O'Hare Intl
Jan 30
ORD11:45 amChicago O'Hare Intl
8h 02m
1 stop
ISP8:47 pmIslip Long Island
$143
Find similar
Frontier
Jan 22
ISP7:43 pmIslip Long Island
15h 52m
1 stop
ORD10:35 amChicago O'Hare Intl
Jan 29
ORD3:55 pmChicago O'Hare Intl
25h 43m
1 stop
ISP6:38 pmIslip Long Island
$184
Find similar
Frontier
Jan 22
ISP7:43 pmIslip Long Island
15h 52m
1 stop
ORD10:35 amChicago O'Hare Intl
Jan 25
ORD12:21 pmChicago O'Hare Intl
29h 27m
1 stop
ISP6:48 pmIslip Long Island
$198
Find similar

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
Jan 20
ISP12:40 pmIslip Long Island
10h 10m
2 stops
ORD9:50 pmChicago O'Hare Intl
Jan 27
ORD6:05 amChicago O'Hare Intl
14h 50m
2 stops
ISP9:55 pmIslip Long Island
$389
Find similar
Southwest
Jan 23
ISP12:40 pmIslip Long Island
10h 10m
2 stops
ORD9:50 pmChicago O'Hare Intl
Jan 30
ORD6:05 amChicago O'Hare Intl
14h 50m
2 stops
ISP9:55 pmIslip Long Island
$403
Find similar
Southwest
Jun 4
ISP6:05 pmIslip Long Island
6h 50m
1 stop
ORD11:55 pmChicago O'Hare Intl
Jun 8
ORD3:20 pmChicago O'Hare Intl
7h 20m
1 stop
ISP11:40 pmIslip Long Island
$437
Find similar

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 December 25, 2025.
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

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 1/13

8:00 am-5:52 pm

1 stop10h 52m

Chicago O'Hare Intl

Wed 1/14

10:48 am-10:46 pm

1 stop10h 58m

$136

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 1/13

8:00 am-5:52 pm

1 stop10h 52m

Chicago O'Hare Intl

Wed 1/14

5:15 am-10:46 pm

2 stops16h 31m

$142

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 1/23

7:33 pm-4:35 pm

1 stop22h 02m

Chicago O'Hare Intl

Fri 1/30

11:45 am-8:47 pm

1 stop8h 02m

$143

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 1/20

12:00 pm-1:13 pm

1 stop26h 13m

Chicago O'Hare Intl

Tue 1/27

7:21 pm-6:55 pm

1 stop22h 34m

$164

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 1/23

7:33 pm-4:35 pm

1 stop22h 02m

Chicago O'Hare Intl

Fri 1/30

8:43 pm-8:40 am

2 stops34h 57m

$171

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 1/20

12:00 pm-11:22 am

2 stops24h 22m

Chicago O'Hare Intl

Tue 1/27

7:21 pm-6:55 pm

1 stop22h 34m

$177

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 1/13

8:00 am-11:46 pm

2 stops16h 46m

Chicago O'Hare Intl

Wed 1/14

5:15 am-10:46 pm

2 stops16h 31m

$180

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 1/22

7:43 pm-10:35 am

1 stop15h 52m

Chicago O'Hare Intl

Thu 1/29

3:55 pm-6:38 pm

1 stop25h 43m

$184

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 1/22

7:43 pm-10:35 am

1 stop15h 52m

Chicago O'Hare Intl

Sun 1/25

12:21 pm-6:48 pm

1 stop29h 27m

$198

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 2/26

5:07 pm-9:40 pm

1 stop29h 33m

Chicago O'Hare Intl

Sun 3/1

2:13 pm-1:32 pm

1 stop22h 19m

$217

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 Wednesday 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 $371.

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 $272 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $366. 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

6h 50m

Direct flights

None
The fastest flight from Islip, New York to Chicago O'Hare Intl Airport takes 6h 50m
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

  • 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 6h 50m.

  • 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 many operators does momondo search for flights from Islip Long Island Airport to Chicago O'Hare Intl Airport?

  • 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.

  • What is the most popular airline from Islip, New York to Chicago O'Hare Intl Airport?

Best airlines flying from Islip, New York to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Islip, New York to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $336Free CancellationRating
8.0
4,257 reviews
Search Southwest flights

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
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Aurora
Elgin
Benton Harbor

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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