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$49+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — CHI
Nov 7 — Nov 141
1 adult
Thu 11/7
Thu 11/14
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Cheap flight deals from Islip to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Islip (ISP) to Chicago (CHI). 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 November 2, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$100
(Frontier)

One-way from

$49
(Cheapflightsfares)
Provider with most accurate pricing for Islip Long Island-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Islip Long Island-Chicago (CHI) flights.
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From Islip Long Island to Chicago (CHI)
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One-way flight from Islip Long Island to Chicago (CHI)
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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 2, 2024.

This Frontier deal was found by Cheapflights users on 11/1. 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.
Sat 11/165:45 amISP - ORD
1 stop12h 56mFrontier
Wed 11/201:11 pmORD - ISP
1 stop10h 33mFrontier
Deal found 11/1$100
This Southwest deal was found by Cheapflights users on 11/1. 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.
Wed 12/46:25 amISP - ORD
1 stop8h 35mSouthwest
Mon 12/95:45 amORD - ISP
1 stop3h 55mSouthwest
Deal found 11/1$366
This Mytrip deal was found by Cheapflights users on 11/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/81:57 pmISP - ORD
3 stops20h 46mMultiple Airlines
Thu 12/123:21 pmORD - ISP
3 stops20h 56mMultiple Airlines
Deal found 11/1$405

Find flights from Islip to Chicago within your budget

Customize your flight search to find flights from Islip to Chicago 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 2,559,957 searches. Data last updated November 2, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 11/20

5:45 am-12:05 pm

1 stop7h 20m

$49

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 11/27

3:15 pm-10:00 pm

1 stop7h 45m

$203

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 12/2

1:57 pm-2:31 pm

3 stops25h 34m

$357

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 11/16

5:45 am-5:41 pm

1 stop12h 56m

Chicago O'Hare Intl

Wed 11/20

1:11 pm-12:44 am

1 stop10h 33m

$100

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 1/23

7:20 pm-8:13 pm

3 stops25h 53m

Chicago O'Hare Intl

Sat 1/25

5:35 am-6:45 pm

1 stop12h 10m

$291

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 12/4

6:25 am-2:00 pm

1 stop8h 35m

Chicago O'Hare Intl

Mon 12/9

5:45 am-10:40 am

1 stop3h 55m

$366

Flights are sorted by cheapest first

Deals found on 11/1

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.
ProviderPrice AccuracyTrust Score*Cancellation Policy
ExpediaPrice Accuracy1 starTrust Score*3 starsCancellation PolicyAirline Policy
FlightHubPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
eDreamsPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy

*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

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

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

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated November 2, 2024.
Read through reviews of airlines operating flights from Islip to Chicago, such as Frontier and Southwest. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,097 reviews

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Boarding

8.3

Food

7.2

Reviews

1 / 10

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

Southwest
8.1
Very good
5,097 reviews
Southwest
8.1
Very good
5,097 reviews

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Boarding

8.3

Food

7.2

Reviews

1 / 10

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

Frontier
6.1
Okay
3,575 reviews
Southwest
8.1
Very good
5,097 reviews

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Boarding

8.3

Food

7.2

Reviews

1 / 10

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

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?

    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 flights from Islip, New York to Chicago for under $100 on Cheapflights?

    Yes, there are multiple flights from Islip, New York to Chicago for under $100. The cheapest flight booked recently is on Frontier for just $100, but on average you can expect to pay $252.

  • Are there last-minute flights available from Islip, New York to Chicago for under $600?

    There are currently 2+ open flights from Islip, New York to Chicago within the next 7 days for less than $600.

  • 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 $100. Another airline that can offer you cheap pricing is Southwest.

  • What does ISP to ORD mean?

    ISP and ORD are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. ISP to ORD refers to a flight route from Islip Long Island Airport to Chicago O'Hare Intl Airport. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Islip to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Islip to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Islip to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Islip to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Islip to Chicago that allow pets onboard?

    Many airlines flying from Islip to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Islip to Chicago?

    Yes, you can often find last-minute deals on Islip to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Islip, New York to Chicago flight deals updated?

    The Islip, New York to Chicago flight deals you see on this page were last updated on 11/1.

  • 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

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Alternative routes for Islip to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Islip to Chicago

Discover the top airline that operate flights from Islip to Chicago. 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 2,559,957 searches. Data last updated November 2, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$243Average$328FlexibilityNo cancel feeOn-time62%
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