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Illinois

$82+ Cheap flights from Islip, NY (ISP) to Illinois

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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — ORD
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
1 adult, Economy
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Cheap flight deals from Islip to Illinois

Cheapest flights from Islip to Illinois
Explore the most affordable flight options available from Islip to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 8, 2025.

This Mytrip deal was found by Cheapflights users on 12/8. 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.
Sat 12/1310:19 amISP - ORD
1 stop28h 12mFrontier
Mon 12/152:26 pmORD - ISP
1 stop28h 08mFrontier
Deal found 12/8$245
This Mytrip deal was found by Cheapflights users on 12/7. 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.
Sat 12/1310:19 amISP - STL
1 stop13h 14mFrontier
Sun 12/143:30 pmSTL - ISP
1 stop16h 43mFrontier
Deal found 12/7$249
This CheapOair deal was found by Cheapflights users on 12/7. 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.
Fri 12/128:29 pmISP - ORD
1 stop17h 47mFrontier
Mon 12/152:26 pmORD - ISP
1 stop28h 08mFrontier
Deal found 12/7$269
This CheapOair deal was found by Cheapflights users on 12/8. 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 12/111:15 pmISP - ORD
1 stop9h 36mFrontier
Fri 12/1212:15 pmORD - ISP
1 stop10h 44mFrontier
Deal found 12/8$299
This CheapOair deal was found by Cheapflights users on 12/7. 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
Fri 1/25:18 pmORD - ISP
1 stop29h 41mFrontier
Deal found 12/7$314
This CheapOair deal was found by Cheapflights users on 12/7. 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 12/111:15 pmISP - ORD
1 stop22h 50mFrontier
Sat 12/132:26 pmORD - ISP
1 stop18h 54mFrontier
Deal found 12/7$323
This CheapOair deal was found by Cheapflights users on 12/8. 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.
Fri 12/128:29 pmISP - ORD
1 stop17h 47mFrontier
Sun 12/142:36 pmORD - ISP
1 stop17h 37mFrontier
Deal found 12/8$333
This CheapOair deal was found by Cheapflights users on 12/8. 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 1/410:12 amORD - ISP
1 stop25h 57mFrontier
Deal found 12/8$358
This Frontier deal was found by Cheapflights users on 12/7. 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 12/1812:20 pmISP - STL
1 stop11h 13mFrontier
Mon 1/510:40 amSTL - ISP
1 stop7h 59mFrontier
Deal found 12/7$367
This Southwest deal was found by Cheapflights users on 12/6. 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.
Mon 12/226:55 amISP - ORD
1 stop9h 30mSouthwest
Wed 1/216:05 amORD - ISP
1 stop7h 30mSouthwest
Deal found 12/6$404
This Frontier deal was found by Cheapflights users on 12/7. 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 12/222:04 pmISP - STL
1 stop9h 29mFrontier
Fri 1/210:40 amSTL - ISP
1 stop8h 00mFrontier
Deal found 12/7$422
This Kiwi.com deal was found by Cheapflights users on 12/7. 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.
Sat 12/1310:19 amISP - ORD
1 stop28h 12mFrontier
Sun 12/143:47 pmORD - ISP
2 stops16h 26mFrontier
Deal found 12/7$428

Find flight deals from Islip to Illinois

Keep the following information in mind while searching for Islip to Illinois flight deals. Data was last updated December 8, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$146
(CheapOair)

One-way from

$82
(CheapOair)

Popular in

August

Cheapest in

January

Average price

$267
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
Search Deals
From Islip Long Island to Illinois
Search Deals
One-way flight from Islip Long Island to Illinois
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 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 Illinois 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 8, 2025.
Use the filters below to find and compare flights from Islip to Illinois that are best for you.

Fly from

Islip

Fly to

Illinois

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 2/9

7:43 pm-4:19 pm

1 stop21h 36m

Chicago O'Hare Intl

Sat 2/14

9:00 am-9:47 am

1 stop23h 47m

$197

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 1/8

8:40 pm-7:17 pm

1 stop23h 37m

Chicago O'Hare Intl

Sun 1/11

8:27 pm-7:51 pm

1 stop22h 24m

$198

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

$201

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Mon 12/29

8:35 pm-9:02 am

1 stop13h 27m

Chicago O'Hare Intl

Fri 1/2

5:18 pm-11:59 pm

1 stop29h 41m

$314

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 1/15

7:58 pm-11:26 am

1 stop16h 28m

Chicago O'Hare Intl

Sun 1/18

7:58 pm-7:50 pm

1 stop22h 52m

$323

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 12/21

2:04 pm-8:47 am

1 stop19h 43m

Chicago O'Hare Intl

Sun 12/28

10:12 am-7:40 pm

1 stop8h 28m

$333

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 12/31

5:27 pm-10:18 am

1 stop17h 51m

Chicago O'Hare Intl

Sun 1/4

10:12 am-1:09 pm

1 stop25h 57m

$358

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 3/12

11:55 am-12:29 am

2 stops13h 34m

Chicago O'Hare Intl

Sun 3/15

2:00 pm-1:31 pm

1 stop22h 31m

$366

IslipSt. Louis

ISP - STL

ISPSTL

Islip Long Island

Fri 12/19

1:27 pm-10:33 pm

1 stop10h 06m

Lambert-St Louis

Fri 1/2

10:40 am-7:40 pm

1 stop8h 00m

$367

IslipSt. Louis

ISP - STL

ISPSTL

Islip Long Island

Fri 12/19

1:27 pm-7:42 pm

1 stop7h 15m

Lambert-St Louis

Mon 1/5

10:40 am-7:39 pm

1 stop7h 59m

$367

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/7

Showing 1-10 of 33 results
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Best time to book a flight from Islip to Illinois

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

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

Currently, May is the cheapest month in which you can book a flight from Islip, New York to Illinois (average of $55). Flying from Islip, New York to Illinois 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 Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated December 8, 2025.
See what other customers who have flown with Southwest from Islip to Illinois have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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 Illinois. 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 Illinois?

    Islip Long Island (ISP), located 7.2 mi from the city center, is the airport you fly out of when you book flights from Islip to Illinois.

  • How long is the flight from Islip, New York to Illinois?

    A quick flight from Islip, New York to Illinois can take about 7h 35m. Frontier provides one of the quickest options available for as low as $398. The distance from Islip, New York to Illinois is about 926 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Islip, New York to Illinois?

    Most travelers choose Islip Long Island - Chicago O'Hare Intl, Islip Long Island - Lambert-St Louis or Islip Long Island - Decatur Arpt when deciding on the best route from Islip, New York to Illinois.

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

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

  • How can I find direct flights from Islip to Illinois?

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

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

    Yes. Cheapflights offers flight deals from Islip to Illinois 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 Illinois?

    Currently, May is the cheapest month in which you can book a flight from Islip, New York to Illinois (average of $55). Flying from Islip, New York to Illinois 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

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Top airline flying from Islip to Illinois

Discover the top airline that operate flights from Islip to Illinois. 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 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$336Average$772FlexibilityNo cancel feeOn-time63%

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