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 $118. Another airline that can offer you cheap pricing is Southwest.

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 31 days early can save you up to 92% on average compared to booking a flight this week. If booking 31 days before your flight isn’t an option for you, users have found flights from Islip, New York to Chicago for as little as $211 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 $362 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 $228. 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 11% 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 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 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.

$84+ Flights from Islip, New York to Chicago, Illinois

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1. Tell us where you want to go

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Cheap flight deals from Islip to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$118 (CheapOair)
One-way from	$84 (Frontier)

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

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 November 20, 2024.

Mon 12/167:52 pmISP - ORD

1 stop17h 54mFrontier

Wed 12/186:55 amORD - ISP

1 stop11h 16mFrontier

Deal found 11/19

$118

Mon 12/163:05 pmISP - ORD

2 stops19h 32mMultiple Airlines

Wed 12/187:53 pmORD - ISP

2 stops16h 24mMultiple Airlines

Deal found 11/19

$314

Wed 11/206:25 amISP - ORD

2 stops9h 35mSouthwest

Wed 11/2711:25 amORD - ISP

1 stop5h 55mSouthwest

Deal found 11/20

$761

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 November 20, 2024.

Mon 12/167:52 pmISP - ORD

1 stop17h 54mFrontier

Wed 12/186:55 amORD - ISP

1 stop11h 16mFrontier

Deal found 11/19

$118

Thu 2/65:55 amISP - ORD

1 stop9h 05mSouthwest

Tue 2/117:00 amORD - ISP

1 stop4h 10mSouthwest

Deal found 11/19

$302

Mon 12/163:05 pmISP - ORD

2 stops19h 32mMultiple Airlines

Wed 12/187:53 pmORD - ISP

2 stops16h 24mMultiple Airlines

Deal found 11/19

$314

Last-minute flights from Islip to Chicago
Discover last-minute flight deals from Islip to Chicago. Data last updated November 20, 2024 and is based on user searches.

Wed 11/206:25 amISP - ORD

2 stops9h 35mSouthwest

Wed 11/2711:25 amORD - ISP

1 stop5h 55mSouthwest

Deal found 11/20

$761

Tue 11/2611:34 amISP - ORD

1 stop8h 42mFrontier

Fri 11/2911:05 amORD - ISP

1 stop12h 39mFrontier

Deal found 11/19

$563

Mon 12/167:52 pmISP - ORD

1 stop17h 54mFrontier

Wed 12/186:55 amORD - ISP

1 stop11h 16mFrontier

Deal found 11/19

$118

Mon 12/163:05 pmISP - ORD

2 stops19h 32mMultiple Airlines

Wed 12/187:53 pmORD - ISP

2 stops16h 24mMultiple Airlines

Deal found 11/19

$314

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 November 20, 2024.

Fri 1/1012:43 pmISP - ORD

1 stop9h 13mFrontier

Deal found 11/19

$84

Wed 12/186:25 amISP - ORD

2 stops7h 35mSouthwest

Deal found 11/20

$156

Find flights from Islip to Chicago within your budget

Fly from

Fly to

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 12/16

7:52 pm-12:46 pm

1 stop17h 54m

Chicago O'Hare Intl

Wed 12/18

6:55 am-7:11 pm

1 stop11h 16m

$118

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 2/6

5:55 am-2:00 pm

1 stop9h 05m

Chicago O'Hare Intl

Tue 2/11

7:00 am-12:10 pm

1 stop4h 10m

$302

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 12/16

3:05 pm-9:37 am

2 stops19h 32m

Chicago O'Hare Intl

Wed 12/18

7:53 pm-1:17 pm

2 stops16h 24m

$314

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 1/10

12:43 pm-8:56 pm

1 stop9h 13m

$84

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 12/18

6:25 am-1:00 pm

2 stops7h 35m

$156

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

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 November.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 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 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 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.

Travel insights for flights from Islip to Chicago

Get recent, data-driven insights about flights from Islip to Chicago including ideal travel times, pricing trends, and more.

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

Currently, September is the cheapest month in which you can book a flight from Islip, New York to Chicago (average of $232). Flying from Islip, New York to Chicago in June is currently the most expensive (average of $308). 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

Southwest

8.1

Very good

5,014 reviews

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest

8.1

Very good

5,014 reviews

Southwest

8.1

Very good

5,014 reviews

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Frontier

6.1

Okay

3,539 reviews

Southwest

8.1

Very good

5,014 reviews

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $118. Another airline that can offer you cheap pricing is Southwest.
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, September is the cheapest month in which you can book a flight from Islip, New York to Chicago (average of $232). Flying from Islip, New York to Chicago in June is currently the most expensive (average of $308). 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

Browse thousands of different options on Cheapflights for your next trip

Top airline flying from Islip to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$243	Average$328	FlexibilityNo cancel fee	On-time62%

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$84+ Cheap flights from Islip (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 1/10. 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

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 November 20, 2024.

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 November 20, 2024.

Find flights from Islip to Chicago within your budget

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 November.

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.

Travel insights for flights from Islip to Chicago

Get recent, data-driven insights about flights from Islip to Chicago including ideal travel times, pricing trends, and more.

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

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?

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?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Islip to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from Islip to Chicago

100% Free

Book with Flexibility

Travel Smart

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 November 20, 2024.