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O'Hare Intl

$76+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — ORD
May 23 — May 301
Sat 5/23
Sat 5/30
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 April 23, 2026.

This Frontier deal was found by Cheapflights users on 4/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/711:12 am
ISP
-
ORD
1 stop13h 01m
Frontier
Mon 5/115:30 pm
ORD
-
ISP
1 stop16h 30m
Frontier
Deal found 4/21$181
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 5/2811:00 am
ISP
-
ORD
1 stop13h 13m
Frontier
Tue 6/26:55 am
ORD
-
ISP
2 stops26h 10m
Frontier
Deal found 4/21$190
This Expedia deal was found by Cheapflights users on 4/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/14:07 pm
ISP
-
ORD
1 stop24h 16m
Frontier
Sun 5/36:00 am
ORD
-
ISP
1 stop26h 13m
Frontier
Deal found 4/18$201
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 5/2811:00 am
ISP
-
ORD
1 stop12h 14m
Multiple Airlines
Tue 6/26:55 am
ORD
-
ISP
2 stops26h 10m
Multiple Airlines
Deal found 4/22$218
This Trip.com deal was found by Cheapflights users on 4/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:31 pm
ISP
-
ORD
1 stop22h 53m
Frontier
Sat 5/95:30 pm
ORD
-
ISP
1 stop15h 57m
Frontier
Deal found 4/21$272
This Trip.com deal was found by Cheapflights users on 4/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:31 pm
ISP
-
ORD
1 stop22h 53m
Frontier
Wed 5/63:55 pm
ORD
-
ISP
1 stop17h 32m
Frontier
Deal found 4/21$273
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Fri 5/1511:00 am
ISP
-
ORD
1 stop13h 13m
Frontier
Sun 5/175:30 pm
ORD
-
ISP
1 stop15h 35m
Frontier
Deal found 4/22$276
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Sun 5/107:53 pm
ISP
-
ORD
2 stops37h 02m
Multiple Airlines
Fri 5/158:30 am
ORD
-
ISP
1 stop8h 44m
Multiple Airlines
Deal found 4/20$290
This Trip.com deal was found by Cheapflights users on 4/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/611:00 am
ISP
-
ORD
1 stop13h 13m
Frontier
Sun 5/105:30 pm
ORD
-
ISP
1 stop15h 35m
Frontier
Deal found 4/21$306
This Southwest deal was found by Cheapflights users on 4/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:30 pm
ISP
-
ORD
2 stops10h 25m
Southwest
Tue 6/25:55 am
ORD
-
ISP
2 stops11h 35m
Southwest
Deal found 4/21$307

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 April 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$181
(Frontier)

One-way from

$76
(Frontier)

Popular in

June

Cheapest in

January

Average price

$275
Provider with most accurate pricing for Islip Long Island-Chicago O'Hare Intl flight deals.
Search Deals
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
Search Deals
One-way flight from Islip Long Island to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

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 April 23, 2026.
Use the filters below to find and compare flights from Islip to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 5/15

11:00 am-11:13 pm

1 stop13h 13m

Chicago O'Hare Intl

Sun 5/17

5:30 pm-10:05 am

1 stop15h 35m

$276

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 5/28

6:00 am-2:20 pm

2 stops9h 20m

Chicago O'Hare Intl

Tue 6/2

5:55 am-6:30 pm

2 stops11h 35m

$307

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 6/23

4:41 pm-11:18 pm

1 stop7h 37m

Chicago O'Hare Intl

Thu 6/25

5:25 pm-10:03 am

1 stop15h 38m

$319

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 5/14

12:30 pm-9:55 pm

2 stops10h 25m

Chicago O'Hare Intl

Mon 5/18

7:35 pm-11:55 am

2 stops15h 20m

$396
Quickest round-trip

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 5/20

6:55 am-6:25 pm

1 stop12h 30m

Chicago O'Hare Intl

Fri 5/22

3:05 pm-10:30 pm

1 stop6h 25m

$412

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 6/27

11:57 am-8:03 am

2 stops45h 06m

Chicago O'Hare Intl

Fri 7/24

5:30 pm-10:03 am

1 stop15h 33m

$416

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 5/15

12:30 pm-9:55 pm

2 stops10h 25m

Chicago O'Hare Intl

Sun 5/17

7:35 pm-11:50 am

2 stops15h 15m

$443

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 6/5

11:00 am-11:13 pm

1 stop13h 13m

Chicago O'Hare Intl

Sun 6/7

7:33 pm-5:58 pm

2 stops21h 25m

$444
Cheapest one-way

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 5/11

6:59 pm-12:23 pm

1 stop18h 24m

$113

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 6/23

4:41 pm-11:19 pm

1 stop7h 38m

$115

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/19

Showing 1-10 of 19 resultsSorted by cheapest first
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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Islip, New York-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

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 April 23, 2026.
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
4,327 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,327 reviews
Southwest
8.0
Very good
4,327 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 and Southwest can get you from Islip, New York to Chicago O'Hare Intl Airport in just under 9h 20m. Your travel time can differ by up to 3h 53m. Islip, New York and Chicago O'Hare Intl Airport are separated by a distance of 770 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 ($387), 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.

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
Rosemont
Schaumburg
Naperville
Gurnee
Lake Geneva
Delavan
Hoffman Estates
Downers Grove
Oakbrook Terrace
Benton Harbor
Des Plaines
Oak Brook
South Holland
Libertyville
Elgin
Warrenville
Elk Grove Village
Bridgeview
Great Lakes
Lansing

Browse thousands of different options on Cheapflights for your next trip

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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 April 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$387Average$1,046FlexibilityNo cancel feeOn-time63%

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