What are the cheapest airlines flying from Islip, New York to Chicago round-trip?

Cheapflights users have booked flights from Islip, New York to Chicago round-trip from $198. Another airline that can offer you cheap pricing is Southwest. Frontier is currently priced 39% below the average price you’ll pay for this route.

What are the cheapest airlines to fly from Islip, New York to Chicago one-way?

One-way options have recently been found by users for as low as $105 on Frontier. Other airlines that offer cheap prices include Southwest from $229 and JetBlue from $726 one-way.

What is the cheapest day to fly from Islip, New York to Chicago?

Travelers seeking maximum savings on their Islip, New York to Chicago flight should consider departing on Friday afternoons when fares are most often at their lowest. Thursday 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?

Users have found that booking a flight from Islip, New York to Chicago 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 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?

September can be a great time to fly to Chicago from Islip, New York with a flight ticket averaging about $226. Cheapflights users have found deals in the month of September for as cheap as $74. The most expensive prices can be found in the month of December.

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

It’s typically best to fly out from Islip, New York to Chicago in the morning. Doing so could potentially save you 16% on the flight price compared to flying at noon, which is usually more expensive.

Most accurate provider : When it comes to deals on Islip, New York-Chicago 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 flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Islip, New York-Chicago flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Islip, New York-Chicago 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 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?

Most people fly from Islip Long Island (ISP) if they book a flight from Islip to Chicago. On average, Long Island has 0 outbound flights to Chicago per day from 1 airline. Islip Long Island is conveniently located just 7.2 mi from Islip’s city center.

Can I find deals for flights from Islip to Chicago that include hotel bookings?

Yes. In addition to deals on Islip to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Islip to Chicago?

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

Can I find deals for business class flights from Islip to Chicago?

Yes. Cheapflights offers flight deals from Islip to Chicago 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

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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

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Cheap flight deals from Islip to Chicago

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	April
Average price	$81

Provider with most accurate pricing for Islip Long Island-Chicago (CHI) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Islip Long Island-Chicago (CHI) flights.

Search Deals

From Islip Long Island to Chicago (CHI)

Search Deals

One-way flight from Islip Long Island to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 20% potential increase in price ($86 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 9% potential price decrease ($27 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 2025

Search Deals

Find flight deals from Islip to Chicago

Cheapest flights from Islip to Chicago
Explore the most affordable flight options available from Islip to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 29, 2025.

Wed 5/217:15 pmISP - ORD

1 stop14h 07mFrontier

Sat 5/241:02 pmORD - ISP

1 stop6h 40mFrontier

Deal found 4/28

$198

Tue 7/226:00 amISP - ORD

1 stop6h 50mSouthwest

Sat 7/2611:25 amORD - ISP

2 stops10h 45mSouthwest

Deal found 4/28

$316

Sat 5/1011:31 amISP - ORD

2 stops12h 58mMultiple Airlines

Sun 5/115:05 amORD - ISP

1 stop11h 53mMultiple Airlines

Deal found 4/28

$366

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

Wed 5/217:15 pmISP - ORD

1 stop14h 07mFrontier

Sat 5/241:02 pmORD - ISP

1 stop6h 40mFrontier

Deal found 4/28

$198

Tue 7/226:00 amISP - ORD

1 stop6h 50mSouthwest

Sat 7/2611:25 amORD - ISP

2 stops10h 45mSouthwest

Deal found 4/28

$316

Sat 5/1011:31 amISP - ORD

2 stops12h 58mMultiple Airlines

Sun 5/115:05 amORD - ISP

1 stop11h 53mMultiple Airlines

Deal found 4/28

$366

Last-minute flights from Islip to Chicago
Discover last-minute flight deals from Islip to Chicago. Data last updated April 29, 2025 and is based on user searches.

Wed 5/77:15 pmISP - ORD

1 stop29h 17mFrontier

Fri 5/99:00 amORD - ISP

1 stop26h 28mFrontier

Deal found 4/29

$211

Fri 5/95:00 amISP - ORD

1 stop9h 05mSouthwest

Sun 5/1111:25 amORD - ISP

2 stops11h 40mSouthwest

Deal found 4/29

$652

Sat 5/1011:31 amISP - ORD

2 stops12h 58mMultiple Airlines

Sun 5/115:05 amORD - ISP

1 stop11h 53mMultiple Airlines

Deal found 4/28

$366

Wed 5/217:15 pmISP - ORD

1 stop14h 07mFrontier

Sat 5/241:02 pmORD - ISP

1 stop6h 40mFrontier

Deal found 4/28

$198

Tue 5/276:10 amISP - ORD

1 stop6h 40mSouthwest

Tue 6/31:50 pmORD - ISP

1 stop5h 30mSouthwest

Deal found 4/29

$327

One-way flights from Islip to Chicago
Search for one-way flight options from Islip to Chicago. Find affordable one-way fares based on user searches. Data last updated April 29, 2025.

Wed 5/217:15 pmISP - ORD

1 stop14h 07mFrontier

Deal found 4/29

$105

Fri 5/235:00 amISP - ORD

2 stops11h 00mSouthwest

Deal found 4/29

$229

Wed 5/72:55 pmISP - ORD

2 stops24h 11mMultiple Airlines

Deal found 4/29

$238

Wed 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 that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 5/28

8:21 pm-8:22 am

1 stop13h 01m

Chicago O'Hare Intl

Sat 5/31

1:02 pm-8:42 pm

1 stop6h 40m

$201

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 7/16

6:00 am-4:25 pm

2 stops11h 25m

Chicago O'Hare Intl

Wed 7/23

6:00 am-5:00 pm

2 stops10h 00m

$321

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 5/10

11:31 am-11:29 pm

2 stops12h 58m

Chicago O'Hare Intl

Sun 5/11

5:05 am-5:58 pm

1 stop11h 53m

$366

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 5/21

7:15 pm-8:22 am

1 stop14h 07m

$105

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 5/23

5:00 am-3:00 pm

2 stops11h 00m

$229

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 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 Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Islip to Chicago 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 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 flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Islip, New York-Chicago flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Islip, New York-Chicago 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 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 Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

What is the cheapest month to book a flight from Islip, New York to Chicago?

Currently, August is the cheapest month in which you can book a flight from Islip, New York to Chicago (average of $245). Flying from Islip, New York to Chicago 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 Chicago by month

In terms of precipitation, rainfall in Chicago 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 when rainfall is around 1.7 in.

Temperature in Chicago by month

If weather is an important factor for your trip to Chicago, 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 Chicago

Read through reviews of airlines operating flights from Islip to Chicago, such as Southwest, JetBlue and Frontier. Users have also rated airlines 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

3,284 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?
Most people fly from Islip Long Island (ISP) if they book a flight from Islip to Chicago. On average, Long Island has 0 outbound flights to Chicago per day from 1 airline. Islip Long Island is conveniently located just 7.2 mi from Islip’s city center.
What are the cheapest airlines flying from Islip, New York to Chicago round-trip?
Cheapflights users have booked flights from Islip, New York to Chicago round-trip from $198. Another airline that can offer you cheap pricing is Southwest. Frontier is currently priced 39% below the average price you’ll pay for this route.
What are the cheapest airlines to fly from Islip, New York to Chicago one-way?
One-way options have recently been found by users for as low as $105 on Frontier. Other airlines that offer cheap prices include Southwest from $229 and JetBlue from $726 one-way.
Can I find deals for flights from Islip to Chicago that include hotel bookings?
Yes. In addition to deals on Islip to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Islip to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Islip to Chicago.
Can I find deals for business class flights from Islip to Chicago?
Yes. Cheapflights offers flight deals from Islip to Chicago 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?
Currently, August is the cheapest month in which you can book a flight from Islip, New York to Chicago (average of $245). Flying from Islip, New York to Chicago 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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Porter

Lansing

Valparaiso

Chesterton

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Top airline flying from Islip to Chicago

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 Chicago (CHI)

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 Chicago 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 Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Islip to Chicago

Cheapest flights from Islip to ChicagoExplore the most affordable flight options available from Islip to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 29, 2025.

Explore the most affordable flight options available from Islip to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 29, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Islip to Chicago that are best for you.

Compare providers for flights from Islip to Chicago

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 Chicago in April.

Best time to book a flight from Islip to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Islip with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Islip to Chicago

What is the cheapest month to book a flight from Islip, New York to Chicago?

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Islip to Chicago, such as Southwest, JetBlue and Frontier. Users have also rated airlines 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 Chicago. 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?

What are the cheapest airlines flying from Islip, New York to Chicago round-trip?

What are the cheapest airlines to fly from Islip, New York to Chicago one-way?

Can I find deals for flights from Islip to Chicago that include hotel bookings?

How can I find direct flights from Islip to Chicago?

Can I find deals for business class flights from Islip to Chicago?

What is the cheapest month to book a flight from Islip, New York to Chicago?

Traveling to a place near Islip?

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Alternative routes for Islip to Chicago

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Top airline flying from Islip to Chicago

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Cheapest flights from Islip to Chicago
Explore the most affordable flight options available from Islip to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 29, 2025.