What are the cheapest airlines flying from Islip, New York to Chicago O'Hare Intl Airport round-trip?

According to our current data, Frontier ($198), and Southwest ($316) offers the cheapest pricing from Islip, New York to Chicago O'Hare Intl Airport.

What are the cheapest airlines to fly from Islip, New York to Chicago O'Hare Intl Airport one-way?

The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $105. However, be on the lookout for offers from Southwest and JetBlue, as they are both options that can get you from Islip, New York to Chicago O'Hare Intl Airport for a low price.

What is the cheapest day to fly from Islip, New York to Chicago O'Hare Intl Airport?

Travelers seeking maximum savings on their Islip, New York to Chicago O'Hare Intl Airport flight should consider departing on Friday mornings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

How far in advance should I book a flight from Islip, New York to Chicago O'Hare Intl Airport?

Users have found that booking a flight from Islip, New York to Chicago O'Hare Intl Airport at least 36 days early can save you up to 90% on average compared to booking a flight this week. If booking 36 days before your flight isn’t an option for you, users have found flights from Islip, New York to Chicago O'Hare Intl Airport for as little as $221 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $357 for flights departing within the next 3 days.

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

The best pricing can be found in the month of September. Prices to Chicago O'Hare Intl Airport from Islip, New York average $226. You can even find prices in September for less than $226, as users have found deals to Chicago O'Hare Intl Airport from as low as $74. The month of December appears to be one of the more expensive times to travel to Chicago O'Hare Intl Airport from Islip, New York. Flying in the targeted month can save you up to 23%.

What is the cheapest time of day to fly from ISP to ORD?

A simple way to save on the total cost of your ticket is to fly from Islip, New York to Chicago O'Hare Intl Airport in the morning. If you’re flexible enough to do this you can expect to save up to 26% on your trip compared to booking a flight at noon.

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 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.

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.

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.

$105+ Flights from Islip, NY to Chicago O'Hare Intl Airport

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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Islip to O'Hare Intl

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$198 (Frontier)
One-way from	$105 (Frontier)
Popular in	December
Cheapest in	September
Average price	$237

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. 2% potential increase in price ($6 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 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 abril 29, 2025.

mié. 5/217:15 pmISP - ORD

1 stop14h 07mFrontier

sáb. 5/241:02 pmORD - ISP

1 stop6h 40mFrontier

Deal found 4/28

$198

mar. 7/226:00 amISP - ORD

1 stop6h 50mSouthwest

sáb. 7/2611:25 amORD - ISP

2 stops10h 45mSouthwest

Deal found 4/28

$316

sáb. 5/1011:31 amISP - ORD

2 stops12h 58mMultiple Airlines

dom. 5/115:05 amORD - ISP

1 stop11h 53mMultiple Airlines

Deal found 4/28

$366

Best flights from Islip to O'Hare Intl
Discover carefully curated flight deals from Islip to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated abril 29, 2025.

mié. 5/217:15 pmISP - ORD

1 stop14h 07mFrontier

sáb. 5/241:02 pmORD - ISP

1 stop6h 40mFrontier

Deal found 4/28

$198

mar. 7/226:00 amISP - ORD

1 stop6h 50mSouthwest

sáb. 7/2611:25 amORD - ISP

2 stops10h 45mSouthwest

Deal found 4/28

$316

sáb. 5/1011:31 amISP - ORD

2 stops12h 58mMultiple Airlines

dom. 5/115:05 amORD - ISP

1 stop11h 53mMultiple Airlines

Deal found 4/28

$366

Last-minute flights from Islip to O'Hare Intl
Discover last-minute flight deals from Islip to O'Hare Intl. Data last updated abril 29, 2025 and is based on user searches.

mié. 5/77:15 pmISP - ORD

1 stop29h 17mFrontier

vie. 5/99:00 amORD - ISP

1 stop26h 28mFrontier

Deal found 4/29

$211

vie. 5/95:00 amISP - ORD

1 stop9h 05mSouthwest

dom. 5/1111:25 amORD - ISP

2 stops11h 40mSouthwest

Deal found 4/29

$652

sáb. 5/1011:31 amISP - ORD

2 stops12h 58mMultiple Airlines

dom. 5/115:05 amORD - ISP

1 stop11h 53mMultiple Airlines

Deal found 4/28

$366

mié. 5/217:15 pmISP - ORD

1 stop14h 07mFrontier

sáb. 5/241:02 pmORD - ISP

1 stop6h 40mFrontier

Deal found 4/28

$198

mar. 5/276:10 amISP - ORD

1 stop6h 40mSouthwest

mar. 6/31:50 pmORD - ISP

1 stop5h 30mSouthwest

Deal found 4/29

$327

One-way flights from Islip to O'Hare Intl
Search for one-way flight options from Islip to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated abril 29, 2025.

mié. 5/217:15 pmISP - ORD

1 stop14h 07mFrontier

Deal found 4/29

$105

vie. 5/235:00 amISP - ORD

2 stops11h 00mSouthwest

Deal found 4/29

$229

mié. 5/72:55 pmISP - ORD

2 stops24h 11mMultiple Airlines

Deal found 4/29

$238

mié. 5/76:00 amISP - ORD

1 stop5h 02mJetBlue

Deal found 4/28

$726

Cheapflights Fare Finder

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

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

mié. 5/28

8:21 pm-8:22 am

1 stop13h 01m

Chicago O'Hare Intl

sáb. 5/31

1:02 pm-8:42 pm

1 stop6h 40m

$201

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

mié. 7/16

6:00 am-4:25 pm

2 stops11h 25m

Chicago O'Hare Intl

mié. 7/23

6:00 am-5:00 pm

2 stops10h 00m

$321

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

sáb. 5/10

11:31 am-11:29 pm

2 stops12h 58m

Chicago O'Hare Intl

dom. 5/11

5:05 am-5:58 pm

1 stop11h 53m

$366

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

mié. 5/21

7:15 pm-8:22 am

1 stop14h 07m

$105

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

vie. 5/23

5:00 am-3:00 pm

2 stops11h 00m

$229

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

mié. 5/7

2:55 pm-2:06 pm

2 stops24h 11m

$238

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Compare providers for flights from Islip to O'Hare Intl

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.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*2 stars
eDreams	Price Accuracy3 stars	Trust 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 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, August is the cheapest month in which you can book a flight from Islip, New York to Chicago O'Hare Intl Airport (average of $245). Flying from Islip, New York 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.

Rainfall in O'Hare Intl by month

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.

Temperature in O'Hare Intl by month

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing O'Hare Intl

To help decide which airline to fly from Islip to Chicago, see what other customers have to say about Southwest, JetBlue and Frontier. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,295 reviews

Reviews

1 / 20

10.0

Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Southwest

8.0

Very good

4,295 reviews

Southwest

8.0

Very good

4,295 reviews

Reviews

1 / 20

10.0

Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

JetBlue

7.3

Good

2,922 reviews

Southwest

8.0

Very good

4,295 reviews

Reviews

1 / 20

10.0

Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Frontier

6.0

Okay

3,287 reviews

Southwest

8.0

Very good

4,295 reviews

Reviews

1 / 20

10.0

Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Related info for your journey

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.
What are the cheapest airlines flying from Islip, New York to Chicago O'Hare Intl Airport round-trip?
According to our current data, Frontier ($198), and Southwest ($316) offers the cheapest pricing from Islip, New York to Chicago O'Hare Intl Airport.
What are the cheapest airlines to fly from Islip, New York to Chicago O'Hare Intl Airport one-way?
The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $105. However, be on the lookout for offers from Southwest and JetBlue, as they are both options that can get you from Islip, New York to Chicago O'Hare Intl Airport for a low price.
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, August is the cheapest month in which you can book a flight from Islip, New York to Chicago O'Hare Intl Airport (average of $245). Flying from Islip, New York 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

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Top airline flying from Islip to O'Hare Intl

Airline	Cheapest	Average	Flexibility	On-time
Southwest	Cheapest$296	Average$366	FlexibilityNo cancel fee	On-time63%

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$105+ 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 5/21. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Islip to O'Hare Intl with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Islip to O'Hare Intl

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Islip to O'Hare Intl

Cheapest flights from Islip to O'Hare IntlExplore 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 abril 29, 2025.

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 abril 29, 2025.

Cheapflights Fare Finder

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

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.

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.

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?

Rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.

Temperature in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.

Reviews of airlines servicing O'Hare Intl

To help decide which airline to fly from Islip to Chicago, see what other customers have to say about Southwest, JetBlue and Frontier. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

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?

What are the cheapest airlines flying from Islip, New York to Chicago O'Hare Intl Airport round-trip?

What are the cheapest airlines to fly from Islip, New York to Chicago O'Hare Intl Airport one-way?

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

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

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

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

Traveling to a place near Islip?

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Alternative routes for Islip to O'Hare Intl

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Top airline flying from Islip to O'Hare Intl

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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 abril 29, 2025.