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Cheap flights from Islip, New York to Chicago from $55

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 12/4. 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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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
6:00 am - 9:48 pmISP-ORD
16h 48m1 stop
Multiple Airlines Logo
2:26 pm - 9:13 amORD-ISP
17h 47m1 stop
$171Multiple Airlines
Find Deal
Wed, Dec 10 - Fri, Dec 12
Multiple Airlines Logo
6:00 am - 12:09 amISP-ORD
19h 09m2 stops
Multiple Airlines Logo
2:26 pm - 9:13 amORD-ISP
17h 47m1 stop
$173Multiple Airlines
Find Deal
Wed, Dec 10 - Fri, Dec 12
Multiple Airlines Logo
6:00 am - 12:39 pmISP-ORD
7h 39m1 stop
Multiple Airlines Logo
2:36 pm - 9:13 amORD-ISP
17h 37m1 stop
$175Multiple Airlines
Find Deal
Fri, Dec 12 - Sun, Dec 14
Frontier Logo
10:19 am - 1:16 pmISP-ORD
27h 57m1 stop
Frontier Logo
2:26 pm - 10:20 amORD-ISP
18h 54m1 stop
$210Frontier
Find Deal
Thu, Dec 11 - Sat, Dec 13
Frontier Logo
6:00 am - 10:36 pmISP-ORD
17h 36m1 stop
Frontier Logo
6:15 pm - 7:34 pmORD-ISP
24h 19m1 stop
$242Frontier
Find Deal
Thu, Nov 27 - Mon, Dec 1
Frontier Logo
8:29 pm - 1:16 pmISP-ORD
17h 47m1 stop
Frontier Logo
2:26 pm - 7:34 pmORD-ISP
28h 08m1 stop
$250Frontier
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Fri, Dec 5 - Mon, Dec 8
Southwest Logo
5:40 am - 2:45 pmISP-ORD
10h 05m2 stops
Southwest Logo
11:55 am - 10:05 pmORD-ISP
9h 10m2 stops
$347Southwest
Find Deal
Mon, Dec 8 - Tue, Dec 9
Southwest Logo
3:40 pm - 9:50 pmISP-ORD
7h 10m1 stop
Southwest Logo
1:45 pm - 11:50 pmORD-ISP
9h 05m2 stops
$358Southwest
Find Deal
Wed, Dec 10 - Fri, Dec 12
Southwest Logo
5:40 am - 2:45 pmISP-ORD
10h 05m2 stops
Southwest Logo
1:45 pm - 11:50 pmORD-ISP
9h 05m2 stops
$363Southwest
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Wed, Dec 10 - Fri, Dec 12
Southwest Logo
1:40 pm - 9:50 pmISP-ORD
9h 10m2 stops
Southwest Logo
1:00 pm - 11:10 pmORD-ISP
9h 10m1 stop
$376Southwest
Find Deal
Thu, Dec 18 - Fri, Dec 19

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
Dec 8
ISP5:40 amIslip Long Island
10h 05m
2 stops
ORD2:45 pmChicago O'Hare Intl
Dec 9
ORD11:55 amChicago O'Hare Intl
9h 10m
2 stops
ISP10:05 pmIslip Long Island
$347
Find similar
Southwest
Dec 10
ISP3:40 pmIslip Long Island
7h 10m
1 stop
ORD9:50 pmChicago O'Hare Intl
Dec 12
ORD1:45 pmChicago O'Hare Intl
9h 05m
2 stops
ISP11:50 pmIslip Long Island
$358
Find similar
Southwest
Dec 10
ISP5:40 amIslip Long Island
10h 05m
2 stops
ORD2:45 pmChicago O'Hare Intl
Dec 12
ORD1:45 pmChicago O'Hare Intl
9h 05m
2 stops
ISP11:50 pmIslip Long Island
$363
Find similar

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
Dec 11
ISP10:19 amIslip Long Island
27h 57m
1 stop
ORD1:16 pmChicago O'Hare Intl
Dec 13
ORD2:26 pmChicago O'Hare Intl
18h 54m
1 stop
ISP10:20 amIslip Long Island
$210
Find similar
Frontier
Nov 27
ISP6:00 amIslip Long Island
17h 36m
1 stop
ORD10:36 pmChicago O'Hare Intl
Dec 1
ORD6:15 pmChicago O'Hare Intl
24h 19m
1 stop
ISP7:34 pmIslip Long Island
$242
Find similar
Frontier
Dec 5
ISP8:29 pmIslip Long Island
17h 47m
1 stop
ORD1:16 pmChicago O'Hare Intl
Dec 8
ORD2:26 pmChicago O'Hare Intl
28h 08m
1 stop
ISP7:34 pmIslip Long Island
$250
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 November 3, 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

Wed 12/10

6:00 am-9:48 pm

1 stop16h 48m

Chicago O'Hare Intl

Fri 12/12

2:26 pm-9:13 am

1 stop17h 47m

$171

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 12/10

6:00 am-12:09 am

2 stops19h 09m

Chicago O'Hare Intl

Fri 12/12

2:26 pm-9:13 am

1 stop17h 47m

$173

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 12/12

6:00 am-12:39 pm

1 stop7h 39m

Chicago O'Hare Intl

Sun 12/14

2:36 pm-9:13 am

1 stop17h 37m

$175

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 12/11

10:19 am-1:16 pm

1 stop27h 57m

Chicago O'Hare Intl

Sat 12/13

2:26 pm-10:20 am

1 stop18h 54m

$210

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 11/27

6:00 am-10:36 pm

1 stop17h 36m

Chicago O'Hare Intl

Mon 12/1

6:15 pm-7:34 pm

1 stop24h 19m

$242

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 12/5

8:29 pm-1:16 pm

1 stop17h 47m

Chicago O'Hare Intl

Mon 12/8

2:26 pm-7:34 pm

1 stop28h 08m

$250

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 12/8

5:40 am-2:45 pm

2 stops10h 05m

Chicago O'Hare Intl

Tue 12/9

11:55 am-10:05 pm

2 stops9h 10m

$347

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 12/10

3:40 pm-9:50 pm

1 stop7h 10m

Chicago O'Hare Intl

Fri 12/12

1:45 pm-11:50 pm

2 stops9h 05m

$358

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 12/10

5:40 am-2:45 pm

2 stops10h 05m

Chicago O'Hare Intl

Fri 12/12

1:45 pm-11:50 pm

2 stops9h 05m

$363

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 12/18

1:40 pm-9:50 pm

2 stops9h 10m

Chicago O'Hare Intl

Fri 12/19

1:00 pm-11:10 pm

1 stop9h 10m

$376

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 $294. 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 $386.

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 $273 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $369. 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

Direct flights

None
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.
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  • 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 10m.

  • 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
4,238 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
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Tinley Park
Janesville
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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