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O'Hare Intl

$75+ Cheap flights from Islip, NY (ISP) to O'Hare Intl (ORD)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — ORD
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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Cheap flight deals from Islip to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Islip (ISP) to O'Hare Intl (ORD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$174
(Kiwi.com)

One-way from

$75
(CheapOair)

Popular in

August

Cheapest in

January

Average price

$242
Provider with most accurate pricing for Islip Long Island-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for Islip Long Island-Chicago O'Hare Intl flights.
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From Islip Long Island to Chicago O'Hare Intl
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One-way flight from Islip Long Island to Chicago O'Hare Intl
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Highest demand for flights based on searches. 7% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Islip to O'Hare Intl

Cheapest flights from Islip to O'Hare Intl
Explore the most affordable flight options available from Islip to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 27, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/410:19 amISP - ORD
1 stop12h 00mMultiple Airlines
Tue 12/94:22 pmORD - ISP
2 stops39h 51mMultiple Airlines
Deal found 10/27$174
This CheapOair deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/144:58 pmISP - ORD
1 stop23h 10mFrontier
Sun 11/167:05 amORD - ISP
1 stop25h 04mFrontier
Deal found 10/26$176
This Mytrip deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/98:57 pmISP - ORD
1 stop16h 19mFrontier
Thu 11/135:25 amORD - ISP
1 stop11h 17mFrontier
Deal found 10/25$178
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/116:27 pmISP - ORD
1 stop29h 39mMultiple Airlines
Thu 11/135:25 amORD - ISP
1 stop11h 17mMultiple Airlines
Deal found 10/26$179
This Booking.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/74:58 pmISP - ORD
1 stop23h 10mFrontier
Sun 11/97:05 amORD - ISP
1 stop25h 04mFrontier
Deal found 10/27$188
This CheapOair deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/98:57 pmISP - ORD
1 stop16h 19mFrontier
Sun 11/167:05 amORD - ISP
1 stop25h 04mFrontier
Deal found 10/27$202
This CheapOair deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/134:05 pmISP - ORD
1 stop25h 03mFrontier
Mon 12/152:26 pmORD - ISP
1 stop28h 08mFrontier
Deal found 10/26$209
This Mytrip deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/104:58 pmISP - ORD
1 stop23h 10mFrontier
Fri 11/145:25 amORD - ISP
1 stop28h 12mFrontier
Deal found 10/26$237
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/174:58 pmISP - ORD
2 stops19h 16mFrontier
Thu 11/206:23 pmORD - ISP
1 stop15h 14mFrontier
Deal found 10/26$239
This CheapOair deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:29 pmISP - ORD
1 stop17h 47mFrontier
Sun 12/72:36 pmORD - ISP
1 stop17h 37mFrontier
Deal found 10/25$242

Cheapflights Fare Finder

 
Customize your flight search to find flights from Islip to O'Hare Intl 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, Cheapflights users made 2,558,603 searches. Data last updated October 27, 2025.
Use the filters below to find and compare flights from Islip to Chicago O'Hare Intl Airport that are best for you.

Fly from

Islip

Fly to

O'Hare Intl

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 12/4

10:19 am-9:19 pm

1 stop12h 00m

Chicago O'Hare Intl

Tue 12/9

4:22 pm-9:13 am

2 stops39h 51m

$174

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 11/14

4:58 pm-3:08 pm

1 stop23h 10m

Chicago O'Hare Intl

Sun 11/16

7:05 am-9:09 am

1 stop25h 04m

$176

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 11/11

6:27 pm-11:06 pm

1 stop29h 39m

Chicago O'Hare Intl

Thu 11/13

5:25 am-5:42 pm

1 stop11h 17m

$179

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 12/13

4:05 pm-4:08 pm

1 stop25h 03m

Chicago O'Hare Intl

Mon 12/15

2:26 pm-7:34 pm

1 stop28h 08m

$209

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 11/10

4:58 pm-3:08 pm

1 stop23h 10m

Chicago O'Hare Intl

Fri 11/14

5:25 am-10:37 am

1 stop28h 12m

$237

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 11/17

4:58 pm-11:14 am

2 stops19h 16m

Chicago O'Hare Intl

Thu 11/20

6:23 pm-10:37 am

1 stop15h 14m

$239

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 12/5

8:29 pm-1:16 pm

1 stop17h 47m

Chicago O'Hare Intl

Sun 12/7

2:36 pm-9:13 am

1 stop17h 37m

$242

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 11/9

11:40 am-12:51 pm

2 stops26h 11m

Chicago O'Hare Intl

Thu 11/13

6:48 am-5:42 pm

1 stop9h 54m

$260

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 12/11

1:15 pm-9:51 pm

1 stop9h 36m

$75

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 11/20

10:02 am-7:26 am

1 stop22h 24m

$81

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 19 results
1
2

Compare providers for flights from Islip to O'Hare Intl

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Islip to O'Hare Intl in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Islip, New York-Chicago O'Hare Intl Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Islip, New York-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Islip, New York-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Islip, New York-Chicago O'Hare Intl Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Islip, New York-Chicago O'Hare Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Islip to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Islip with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Islip to Chicago O'Hare Intl Airport

What is the cheapest month to book a flight from Islip, New York to Chicago O'Hare Intl Airport?

Currently, November is the cheapest month in which you can book a flight from Islip, New York to Chicago O'Hare Intl Airport (average of $66). Flying from Islip, New York to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $126). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to O'Hare Intl. Reviews last updated October 27, 2025.
See what other customers who have flown with Southwest from Islip to Chicago O'Hare Intl Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,236 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Islip to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Islip to Chicago O'Hare Intl?

    Islip Long Island (ISP), located 7.2 mi from the city center, is the airport you fly out of when you book flights from Islip to Chicago O'Hare Intl. 1 airline have flights from Long Island to Chicago O'Hare Intl on a regular basis. Booking flights from Islip Long Island to Chicago O'Hare Intl should not be difficult; the airport handles an average of 0 outbound flights to Chicago O'Hare Intl per day.

  • How long is the flight from Islip, New York to Chicago O'Hare Intl Airport?

    Frontier can get you from Islip, New York to Chicago O'Hare Intl Airport in just under 23h 10m. Your travel time can differ by up to . Islip, New York and Chicago O'Hare Intl Airport are separated by a distance of 770 mi.

  • What is the cheapest airline to fly from Islip, New York to Chicago O'Hare Intl Airport round-trip?

    According to our current data, Southwest ($336), offers the cheapest pricing from Islip, New York to Chicago O'Hare Intl Airport.

  • Can I find deals for flights from Islip to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Islip to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Islip to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Islip to O'Hare Intl.

  • Can I find deals for business class flights from Islip to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Islip to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Islip, New York to Chicago O'Hare Intl Airport?

    Currently, November is the cheapest month in which you can book a flight from Islip, New York to Chicago O'Hare Intl Airport (average of $66). Flying from Islip, New York to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $126). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Skokie
Des Plaines
Gurnee
Hoffman Estates
Elgin
Oak Brook
Elk Grove Village
Beloit
Rockford
Naperville
Racine
Downers Grove
Orland Park
Merrillville
Bridgeview
Warrenville
Joliet
Waukegan

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Islip to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
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Elmira to Midway flights
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Stewart to Midway flights
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Top airline flying from Islip to O'Hare Intl

Discover the top airline that operate flights from Islip to O'Hare Intl. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$336Average$772FlexibilityNo cancel feeOn-time63%

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