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O'Hare Intl

$82+ 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — ORD
ene. 11 — ene. 181
dom. 1/11
dom. 1/18
1 adult, Economy
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Cheap 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 diciembre 12, 2025.

This CheapOair deal was found by Cheapflights users on 12/9. 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.
sáb. 12/1310:19 amISP - ORD
1 stop28h 12mFrontier
lun. 12/152:26 pmORD - ISP
1 stop28h 08mFrontier
Deal found 12/9$265
This CheapOair deal was found by Cheapflights users on 12/10. 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.
jue. 12/111:15 pmISP - ORD
1 stop22h 50mFrontier
lun. 12/152:26 pmORD - ISP
1 stop28h 08mFrontier
Deal found 12/10$294
This Priceline deal was found by Cheapflights users on 12/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/111:15 pmISP - ORD
1 stop9h 36mFrontier
vie. 12/1212:15 pmORD - ISP
1 stop10h 44mFrontier
Deal found 12/9$327
This CheapOair deal was found by Cheapflights users on 12/11. 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.
mié. 12/315:27 pmISP - ORD
1 stop17h 51mFrontier
dom. 1/410:12 amORD - ISP
1 stop25h 57mFrontier
Deal found 12/11$383
This CheapOair deal was found by Cheapflights users on 12/9. 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.
jue. 12/2512:20 pmISP - ORD
1 stop21h 32mFrontier
lun. 12/299:47 amORD - ISP
1 stop8h 53mFrontier
Deal found 12/9$423
This CheapOair deal was found by Cheapflights users on 12/11. 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.
vie. 12/128:29 pmISP - ORD
1 stop17h 47mFrontier
dom. 12/142:36 pmORD - ISP
1 stop17h 37mFrontier
Deal found 12/11$428
This CheapOair deal was found by Cheapflights users on 12/11. 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.
mar. 12/2312:20 pmISP - ORD
1 stop22h 58mFrontier
mar. 12/3010:12 amORD - ISP
1 stop29h 25mFrontier
Deal found 12/11$473
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
jue. 12/1110:19 amISP - ORD
2 stops14h 50mMultiple Airlines
vie. 12/122:26 pmORD - ISP
1 stop17h 47mMultiple Airlines
Deal found 12/9$483

Find 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 diciembre 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$146
(CheapOair)

One-way from

$82
(CheapOair)

Popular in

August

Cheapest in

January

Average price

$267
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. 8% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
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 December 2025
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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 diciembre 12, 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

lun. 3/9

1:42 pm-11:38 pm

1 stop10h 56m

Chicago O'Hare Intl

jue. 3/12

4:18 pm-12:47 pm

1 stop19h 29m

$163

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

jue. 1/15

7:58 pm-11:26 am

1 stop16h 28m

Chicago O'Hare Intl

sáb. 1/17

3:49 pm-8:55 am

1 stop16h 06m

$182

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

jue. 1/8

8:40 pm-5:52 pm

1 stop22h 12m

Chicago O'Hare Intl

jue. 1/15

4:41 pm-7:50 pm

2 stops26h 09m

$214

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

mar. 1/6

12:00 pm-12:39 pm

1 stop25h 39m

Chicago O'Hare Intl

vie. 1/9

8:27 pm-7:08 pm

1 stop21h 41m

$219

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

mar. 2/17

11:59 am-8:13 am

1 stop21h 14m

Chicago O'Hare Intl

jue. 2/19

4:42 pm-1:31 pm

2 stops19h 49m

$282

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

jue. 1/15

9:52 am-7:41 pm

1 stop10h 49m

Chicago O'Hare Intl

vie. 1/16

12:31 pm-8:09 pm

1 stop6h 38m

$292

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

jue. 3/12

5:08 pm-11:38 pm

1 stop7h 30m

Chicago O'Hare Intl

dom. 3/15

4:18 pm-12:47 pm

1 stop19h 29m

$322

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

vie. 1/16

8:54 pm-2:39 pm

1 stop18h 45m

Chicago O'Hare Intl

dom. 1/18

7:58 pm-7:50 pm

1 stop22h 52m

$392

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

mar. 1/27

9:15 am-9:50 pm

1 stop13h 35m

Chicago O'Hare Intl

jue. 1/29

6:05 am-2:35 pm

1 stop7h 30m

$400

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

mié. 12/31

5:27 pm-10:18 am

1 stop17h 51m

Chicago O'Hare Intl

dom. 1/4

10:12 am-1:09 pm

1 stop25h 57m

$408

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 22 results
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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 December.
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 $55). 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 diciembre 12, 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
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 10h 56m. 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 $55). 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
Gurnee
Elgin
Naperville
Hoffman Estates
Beloit
Delavan
Oak Brook
Downers Grove
Des Plaines
Elk Grove Village
Skokie
Lake Geneva
Bridgeview
Warrenville
Waukegan
Aurora
Kenosha
Evanston

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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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 diciembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$336Average$772FlexibilityNo cancel feeOn-time63%

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