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$71+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — CHI
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap 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 December 23, 2025.

This CheapOair deal was found by Cheapflights users on 12/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:27 pmISP - ORD
1 stop17h 51mFrontier
Sun 1/48:09 pmORD - ISP
1 stop16h 00mFrontier
Deal found 12/23$373
This CheapOair deal was found by Cheapflights users on 12/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/298:35 pmISP - ORD
1 stop13h 27mFrontier
Tue 12/307:01 pmORD - ISP
1 stop20h 36mFrontier
Deal found 12/23$388
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/262:25 pmISP - ORD
2 stops29h 08mMultiple Airlines
Thu 1/17:20 amORD - ISP
1 stop28h 49mMultiple Airlines
Deal found 12/22$611
This CheapOair deal was found by Cheapflights users on 12/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2512:20 pmISP - ORD
1 stop21h 32mFrontier
Mon 1/59:47 amORD - ISP
1 stop8h 52mFrontier
Deal found 12/22$682
This Frontier deal was found by Cheapflights users on 12/22. 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.
Mon 12/298:35 pmISP - ORD
1 stop13h 27mFrontier
Sat 1/310:12 amORD - ISP
1 stop7h 33mFrontier
Deal found 12/22$721
This Southwest deal was found by Cheapflights users on 12/22. 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.
Fri 12/2612:40 pmISP - ORD
2 stops10h 10mSouthwest
Thu 1/16:05 amORD - ISP
2 stops8h 00mSouthwest
Deal found 12/22$827
This CheapOair deal was found by Cheapflights users on 12/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:27 pmISP - ORD
1 stop17h 51mFrontier
Fri 1/25:18 pmORD - ISP
1 stop29h 41mFrontier
Deal found 12/22$882
This CheapOair deal was found by Cheapflights users on 12/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:25 amISP - ORD
1 stop7h 09mFrontier
Tue 12/2310:12 amORD - ISP
1 stop29h 25mFrontier
Deal found 12/21$1,081
This CheapOair deal was found by Cheapflights users on 12/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:00 amISP - ORD
1 stop19h 31mFrontier
Mon 12/2912:25 pmORD - ISP
1 stop10h 34mFrontier
Deal found 12/23$1,121
This Frontier deal was found by Cheapflights users on 12/22. 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.
Fri 12/268:35 pmISP - ORD
1 stop13h 32mFrontier
Sun 12/2810:12 amORD - ISP
1 stop8h 28mFrontier
Deal found 12/22$1,140

Find 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 December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$136
(Trip.com)

One-way from

$71
(CheapOair)

Popular in

July

Cheapest in

April

Average price

$386
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. 22% potential increase in price ($99 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
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 2,558,603 searches. Data last updated December 23, 2025.
Use the filters below to find and compare flights from Islip to Chicago that are best for you.

Fly from

Islip

Fly to

Chicago

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 1/13

8:00 am-5:52 pm

1 stop10h 52m

Chicago O'Hare Intl

Wed 1/14

10:48 am-10:46 pm

1 stop10h 58m

$136

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 1/20

12:00 pm-1:13 pm

1 stop26h 13m

Chicago O'Hare Intl

Tue 1/27

7:21 pm-6:55 pm

1 stop22h 34m

$164

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 1/25

11:55 am-11:59 pm

2 stops13h 04m

Chicago O'Hare Intl

Thu 1/29

3:55 pm-6:38 pm

1 stop25h 43m

$171

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 1/22

7:43 pm-10:35 am

1 stop15h 52m

Chicago O'Hare Intl

Sun 1/25

12:21 pm-6:48 pm

1 stop29h 27m

$198

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 1/23

7:33 pm-4:35 pm

1 stop22h 02m

Chicago O'Hare Intl

Sat 1/31

9:25 am-8:40 am

1 stop22h 15m

$198

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 1/23

7:33 pm-4:35 pm

1 stop22h 02m

Chicago O'Hare Intl

Sun 1/25

12:21 pm-6:48 pm

1 stop29h 27m

$233

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 1/16

8:54 pm-2:39 pm

1 stop18h 45m

Chicago O'Hare Intl

Sun 1/18

7:58 pm-7:50 pm

1 stop22h 52m

$287

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 1/7

11:50 am-9:12 am

2 stops22h 22m

Chicago O'Hare Intl

Sun 1/11

8:27 pm-7:51 pm

1 stop22h 24m

$291

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 3/13

1:42 pm-11:38 pm

1 stop10h 56m

Chicago O'Hare Intl

Sun 3/22

4:38 pm-9:48 am

1 stop16h 10m

$363

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 3/16

9:27 am-11:26 am

2 stops26h 59m

Chicago O'Hare Intl

Thu 3/19

10:07 am-8:42 am

2 stops21h 35m

$376

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 20 results
1
2

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Islip, New York-Chicago flight deals on Cheapflights vs. eDreams >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, December is the cheapest month in which you can book a flight from Islip, New York to Chicago (average of $48). Flying from Islip, New York to Chicago in July is currently the most expensive (average of $126). 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 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 December 23, 2025.
Read reviews from past customers who have flown Southwest from Islip to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,255 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,255 reviews
Southwest
8.0
Very good
4,255 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • What is the cheapest airline to fly from Islip, New York to Chicago round-trip?

    Cheapflights users have booked flights from Islip, New York to Chicago round-trip from $336. Southwest is currently priced 4% below the average price you’ll pay for this route.

  • 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, December is the cheapest month in which you can book a flight from Islip, New York to Chicago (average of $48). Flying from Islip, New York to Chicago in July is currently the most expensive (average of $126). 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?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 2,558,603 searches. Data last updated December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$336Average$892FlexibilityNo cancel feeOn-time63%

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