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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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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 September 15, 2025.

Round-trip from

$168
(Frontier)

One-way from

$84
(Frontier)

Popular in

July

Cheapest in

April

Average price

$323
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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Highest demand for flights based on searches. 16% potential increase in price ($72 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 15, 2025.

This Frontier deal was found by Cheapflights users on 9/13. 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.
Thu 9/2511:40 amISP - ORD
1 stop9h 04mFrontier
Sun 9/288:49 pmORD - ISP
1 stop12h 51mFrontier
Deal found 9/13$168
This Trip.com deal was found by Cheapflights users on 9/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/3011:25 amISP - ORD
1 stop11h 33mMultiple Airlines
Fri 10/38:49 pmORD - ISP
1 stop13h 06mMultiple Airlines
Deal found 9/13$207
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Tue 10/79:37 pmISP - ORD
1 stop21h 16mMultiple Airlines
Wed 10/226:58 pmORD - ISP
1 stop24h 44mMultiple Airlines
Deal found 9/13$218
This Frontier deal was found by Cheapflights users on 9/14. 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.
Thu 9/1811:40 amISP - ORD
1 stop9h 04mFrontier
Sun 9/218:49 pmORD - ISP
1 stop12h 51mFrontier
Deal found 9/14$224
This Frontier deal was found by Cheapflights users on 9/14. 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.
Sun 10/199:47 pmISP - ORD
2 stops14h 31mFrontier
Wed 10/223:12 pmORD - ISP
2 stops16h 52mFrontier
Deal found 9/14$227
This Frontier deal was found by Cheapflights users on 9/12. 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.
Thu 10/211:40 amISP - ORD
2 stops12h 40mFrontier
Sun 10/58:49 pmORD - ISP
1 stop12h 51mFrontier
Deal found 9/12$230
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Mon 11/32:25 pmISP - ORD
1 stop10h 03mMultiple Airlines
Thu 11/61:50 pmORD - ISP
1 stop22h 55mMultiple Airlines
Deal found 9/14$235
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Mon 10/204:58 pmISP - ORD
1 stop25h 55mMultiple Airlines
Mon 10/275:28 pmORD - ISP
1 stop15h 30mMultiple Airlines
Deal found 9/14$251
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/244:58 pmISP - ORD
1 stop23h 41mMultiple Airlines
Sun 10/266:54 pmORD - ISP
1 stop14h 43mMultiple Airlines
Deal found 9/12$262

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 September 15, 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

Thu 9/25

11:40 am-7:44 pm

1 stop9h 04m

Chicago O'Hare Intl

Fri 9/26

8:49 pm-10:55 am

1 stop13h 06m

$168

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 9/25

11:40 am-7:44 pm

1 stop9h 04m

Chicago O'Hare Intl

Sun 9/28

8:49 pm-10:40 am

1 stop12h 51m

$168

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 10/9

9:37 pm-7:34 am

1 stop10h 57m

Chicago O'Hare Intl

Sun 10/12

8:14 am-8:52 pm

1 stop11h 38m

$184

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Tue 10/7

9:37 pm-5:53 pm

1 stop21h 16m

Chicago O'Hare Intl

Wed 10/22

6:58 pm-8:42 pm

1 stop24h 44m

$218

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 9/28

11:25 am-7:44 pm

1 stop9h 19m

Chicago O'Hare Intl

Sun 10/5

8:49 pm-10:40 am

1 stop12h 51m

$224

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 11/3

2:25 pm-11:28 pm

1 stop10h 03m

Chicago O'Hare Intl

Thu 11/6

1:50 pm-1:45 pm

1 stop22h 55m

$235

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 10/20

4:58 pm-5:53 pm

1 stop25h 55m

Chicago O'Hare Intl

Mon 10/27

5:28 pm-9:58 am

1 stop15h 30m

$251

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 10/24

4:58 pm-3:39 pm

1 stop23h 41m

Chicago O'Hare Intl

Sun 10/26

6:54 pm-10:37 am

1 stop14h 43m

$262

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 9/25

11:40 am-7:44 pm

1 stop9h 04m

$84

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 10/9

9:37 pm-7:34 am

1 stop10h 57m

$106

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 14 results
1
2

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 to Chicago?

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

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 September 15, 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
4,242 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Islip to Chicago?

    Airlines like Frontier fly from Islip to Chicago in about 9h 04m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 770 mi.

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

    Cheapflights users have booked flights from Islip to Chicago round-trip from $306. This flight start at 18% lower than the current average price 3 months from now.

  • 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 to Chicago?

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

Traveling to a place near Chicago?

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

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$336Average$546FlexibilityNo cancel feeOn-time63%

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