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O'Hare Intl

$89+ Cheap flights from Islip (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 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — ORD
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$193
(Kiwi.com)

One-way from

$89
(Frontier)

Popular in

August

Cheapest in

January

Average price

$185
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. 4% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1811:40 amISP - ORD
1 stop9h 04mFrontier
Sun 9/218:49 pmORD - ISP
1 stop12h 51mFrontier
Deal found 9/10$178
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Thu 10/99:37 pmISP - ORD
1 stop10h 57mFrontier
Thu 10/166:07 pmORD - ISP
1 stop15h 30mFrontier
Deal found 9/9$193
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2511:40 amISP - ORD
1 stop9h 04mFrontier
Mon 9/298:49 pmORD - ISP
1 stop12h 51mFrontier
Deal found 9/10$194
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2511:40 amISP - ORD
1 stop9h 04mFrontier
Sun 9/288:49 pmORD - ISP
1 stop12h 51mFrontier
Deal found 9/10$203
This Frontier deal was found by Cheapflights users on 9/8. 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 10/211:40 amISP - ORD
1 stop9h 04mFrontier
Sun 10/58:49 pmORD - ISP
1 stop12h 51mFrontier
Deal found 9/8$208
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Wed 9/2411:35 amISP - ORD
1 stop29h 37mMultiple Airlines
Sun 9/288:49 pmORD - ISP
1 stop12h 51mMultiple Airlines
Deal found 9/9$216
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/174:58 pmISP - ORD
1 stop23h 41mFrontier
Mon 10/206:23 pmORD - ISP
1 stop25h 19mFrontier
Deal found 9/8$221
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/169:37 pmISP - ORD
2 stops14h 41mFrontier
Mon 10/205:50 pmORD - ISP
2 stops14h 54mFrontier
Deal found 9/10$227
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 9/125:05 pmISP - ORD
1 stop23h 12mFrontier
Mon 9/158:49 pmORD - ISP
1 stop12h 51mFrontier
Deal found 9/9$232

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 September 11, 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 9/18

11:40 am-7:44 pm

1 stop9h 04m

Chicago O'Hare Intl

Sun 9/21

8:49 pm-10:40 am

1 stop12h 51m

$178

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 9/25

11:40 am-7:44 pm

1 stop9h 04m

Chicago O'Hare Intl

Mon 9/29

8:49 pm-10:40 am

1 stop12h 51m

$194

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 9/25

11:40 am-7:44 pm

1 stop9h 04m

Chicago O'Hare Intl

Sun 9/28

8:49 pm-10:40 am

1 stop12h 51m

$203

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 10/2

11:40 am-7:44 pm

1 stop9h 04m

Chicago O'Hare Intl

Sun 10/5

8:49 pm-10:40 am

1 stop12h 51m

$203

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 9/24

11:35 am-4:12 pm

1 stop29h 37m

Chicago O'Hare Intl

Sun 9/28

8:49 pm-10:40 am

1 stop12h 51m

$216

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 10/17

4:58 pm-3:39 pm

1 stop23h 41m

Chicago O'Hare Intl

Mon 10/20

6:23 pm-8:42 pm

1 stop25h 19m

$221

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 9/21

11:25 am-7:44 pm

1 stop9h 19m

Chicago O'Hare Intl

Sun 9/28

8:49 pm-10:40 am

1 stop12h 51m

$234

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 9/18

11:40 am-7:44 pm

1 stop9h 04m

$89

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 10/9

9:37 pm-7:34 am

1 stop10h 57m

$111

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 9/28

11:25 am-7:44 pm

1 stop9h 19m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 13 results
1
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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 to Chicago O'Hare Intl Airport?

Currently, August is the cheapest month in which you can book a flight from Islip to Chicago O'Hare Intl Airport (average of $245). Flying from Islip to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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 September 11, 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
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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 to Chicago O'Hare Intl Airport?

    Departing from Islip to Chicago O'Hare Intl Airport will take you 9h 04m. Islip and Chicago O'Hare Intl Airport are separated by a distance of 770 mi.

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

    Currently priced at $336, Southwest will fly you from Islip to Chicago O'Hare Intl Airport and back. In addition to Southwest, many other airlines offer competitively priced options for your trip.

  • 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 to Chicago O'Hare Intl Airport?

    Currently, August is the cheapest month in which you can book a flight from Islip to Chicago O'Hare Intl Airport (average of $245). Flying from Islip to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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
Gurnee
Hoffman Estates
Des Plaines
Elgin
Arlington Heights
Beloit
Racine
Rockford
Orland Park
Oak Brook
Downers Grove
Naperville
Elk Grove Village
Evanston
Merrillville
Bridgeview
Warrenville

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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Stewart to Rockford flights

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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$336Average$546FlexibilityNo cancel feeOn-time63%

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