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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.
Frontier Logo
3:59 pm - 3:52 pm
ISP
-
ORD
24h 53m
1 stop
Frontier Logo
3:11 pm - 11:06 am
ORD
-
ISP
18h 55m
1 stop
$202Frontier
Mon, Feb 23 - Fri, Feb 27
Multiple Airlines Logo
8:33 am - 5:46 pm
ISP
-
ORD
10h 13m
1 stop
Multiple Airlines Logo
12:44 pm - 8:40 am
ORD
-
ISP
18h 56m
1 stop
$218Multiple Airlines
Fri, Feb 20 - Tue, Feb 24
Multiple Airlines Logo
6:49 pm - 2:47 pm
ISP
-
ORD
20h 58m
1 stop
Multiple Airlines Logo
10:25 am - 9:13 am
ORD
-
ISP
21h 48m
1 stop
$230Multiple Airlines
Wed, Apr 22 - Sun, Apr 26
Multiple Airlines Logo
3:34 pm - 7:54 am
ISP
-
ORD
17h 20m
2 stops
Multiple Airlines Logo
12:44 pm - 8:40 am
ORD
-
ISP
18h 56m
1 stop
$233Multiple Airlines
Fri, Feb 20 - Tue, Feb 24
Multiple Airlines Logo
11:41 am - 7:47 pm
ISP
-
ORD
9h 06m
1 stop
Multiple Airlines Logo
5:58 pm - 2:39 pm
ORD
-
ISP
19h 41m
2 stops
$239Multiple Airlines
Sat, Feb 21 - Wed, Feb 25
Multiple Airlines Logo
11:41 am - 7:47 pm
ISP
-
ORD
9h 06m
1 stop
Multiple Airlines Logo
10:44 am - 2:39 pm
ORD
-
ISP
26h 55m
1 stop
$240Multiple Airlines
Sat, Feb 21 - Wed, Feb 25
Multiple Airlines Logo
2:31 pm - 11:37 pm
ISP
-
ORD
10h 06m
1 stop
Multiple Airlines Logo
8:39 am - 11:06 am
ORD
-
ISP
25h 27m
2 stops
$242Multiple Airlines
Mon, Feb 23 - Fri, Feb 27
Multiple Airlines Logo
11:59 am - 10:01 pm
ISP
-
ORD
11h 02m
1 stop
Multiple Airlines Logo
3:28 pm - 11:10 am
ORD
-
ISP
18h 42m
2 stops
$272Multiple Airlines
Tue, Mar 10 - Tue, Mar 17
Multiple Airlines Logo
3:50 pm - 10:44 am
ISP
-
ORD
19h 54m
2 stops
Multiple Airlines Logo
3:49 pm - 9:13 am
ORD
-
ISP
16h 24m
1 stop
$279Multiple Airlines
Sun, Apr 19 - Wed, Apr 22
Multiple Airlines Logo
11:50 am - 10:44 am
ISP
-
ORD
23h 54m
2 stops
Multiple Airlines Logo
10:25 am - 9:13 am
ORD
-
ISP
21h 48m
1 stop
$281Multiple Airlines
Wed, Apr 22 - Sun, Apr 26

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
Feb 23
ISP3:59 pmIslip Long Island
24h 53m
1 stop
ORD3:52 pmChicago O'Hare Intl
Feb 27
ORD3:11 pmChicago O'Hare Intl
18h 55m
1 stop
ISP11:06 amIslip Long Island
$202
Frontier
May 8
ISP3:50 pmIslip Long Island
20h 53m
1 stop
ORD11:43 amChicago O'Hare Intl
May 10
ORD10:25 amChicago O'Hare Intl
21h 48m
1 stop
ISP9:13 amIslip Long Island
$325
Frontier
Mar 6
ISP1:42 pmIslip Long Island
28h 10m
1 stop
ORD4:52 pmChicago O'Hare Intl
Mar 8
ORD5:05 pmChicago O'Hare Intl
15h 58m
1 stop
ISP10:03 amIslip Long Island
$448

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
Mar 10
ISP5:45 amIslip Long Island
11h 20m
2 stops
ORD4:05 pmChicago O'Hare Intl
Mar 17
ORD2:40 pmChicago O'Hare Intl
7h 10m
2 stops
ISP10:50 pmIslip Long Island
$329
Southwest
Mar 10
ISP6:10 amIslip Long Island
13h 25m
1 stop
ORD6:35 pmChicago O'Hare Intl
Mar 17
ORD1:35 pmChicago O'Hare Intl
8h 05m
1 stop
ISP10:40 pmIslip Long Island
$358
Southwest
Apr 19
ISP11:50 amIslip Long Island
11h 05m
2 stops
ORD9:55 pmChicago O'Hare Intl
Apr 22
ORD5:55 amChicago O'Hare Intl
11h 35m
2 stops
ISP6:30 pmIslip Long Island
$363

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 February 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

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 2/23

3:59 pm-3:52 pm

1 stop24h 53m

Chicago O'Hare Intl

Fri 2/27

3:11 pm-11:06 am

1 stop18h 55m

$202

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 2/20

8:33 am-5:46 pm

1 stop10h 13m

Chicago O'Hare Intl

Tue 2/24

12:44 pm-8:40 am

1 stop18h 56m

$218

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 4/22

6:49 pm-2:47 pm

1 stop20h 58m

Chicago O'Hare Intl

Sun 4/26

10:25 am-9:13 am

1 stop21h 48m

$230

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 2/20

3:34 pm-7:54 am

2 stops17h 20m

Chicago O'Hare Intl

Tue 2/24

12:44 pm-8:40 am

1 stop18h 56m

$233

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 2/21

11:41 am-7:47 pm

1 stop9h 06m

Chicago O'Hare Intl

Wed 2/25

5:58 pm-2:39 pm

2 stops19h 41m

$239

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 2/21

11:41 am-7:47 pm

1 stop9h 06m

Chicago O'Hare Intl

Wed 2/25

10:44 am-2:39 pm

1 stop26h 55m

$240

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 2/23

2:31 pm-11:37 pm

1 stop10h 06m

Chicago O'Hare Intl

Fri 2/27

8:39 am-11:06 am

2 stops25h 27m

$242

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 3/10

11:59 am-10:01 pm

1 stop11h 02m

Chicago O'Hare Intl

Tue 3/17

3:28 pm-11:10 am

2 stops18h 42m

$272

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 4/19

3:50 pm-10:44 am

2 stops19h 54m

Chicago O'Hare Intl

Wed 4/22

3:49 pm-9:13 am

1 stop16h 24m

$279

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 4/22

11:50 am-10:44 am

2 stops23h 54m

Chicago O'Hare Intl

Sun 4/26

10:25 am-9:13 am

1 stop21h 48m

$281

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 $366.

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 $270 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $362. 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 $366Free CancellationRating
8.0
4,282 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
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Merrillville
Gurnee
Naperville
Rosemont
New Buffalo
Kenosha
Oak Brook
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Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
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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