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$80+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — ORD
Feb 23 — Mar 21
Mon 2/23
Mon 3/2
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 January 24, 2026.

This CheapOair deal was found by Cheapflights users on 1/21. 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 2/238:23 am
ISP
-
ORD
1 stop15h 52m
Frontier
Sat 2/288:15 am
ORD
-
ISP
1 stop22h 33m
Frontier
Deal found 1/21$160
This Kiwi.com deal was found by Cheapflights users on 1/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/208:33 am
ISP
-
ORD
1 stop12h 14m
Multiple Airlines
Tue 2/2410:19 am
ORD
-
ISP
2 stops23h 51m
Multiple Airlines
Deal found 1/23$203
This Gotogate deal was found by Cheapflights users on 1/22. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/67:33 pm
ISP
-
ORD
1 stop22h 02m
Frontier
Tue 2/108:30 am
ORD
-
ISP
1 stop27h 43m
Frontier
Deal found 1/22$204
This Expedia deal was found by Cheapflights users on 1/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/208:33 am
ISP
-
ORD
1 stop12h 39m
Frontier
Tue 2/248:30 am
ORD
-
ISP
1 stop23h 10m
Frontier
Deal found 1/23$216
This CheapOair deal was found by Cheapflights users on 1/22. 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.
Fri 2/273:34 pm
ISP
-
ORD
1 stop25h 03m
Frontier
Sun 3/17:35 am
ORD
-
ISP
1 stop23h 03m
Frontier
Deal found 1/22$230
This Southwest deal was found by Cheapflights users on 1/22. 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.
Mon 3/92:00 pm
ISP
-
STL
1 stop4h 50m
Southwest
Wed 3/116:15 am
STL
-
ISP
1 stop4h 25m
Southwest
Deal found 1/22$251
This Southwest deal was found by Cheapflights users on 1/22. 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.
Sat 3/76:00 pm
ISP
-
STL
1 stop6h 50m
Southwest
Mon 3/94:45 pm
STL
-
ISP
1 stop6h 10m
Southwest
Deal found 1/22$259
This CheapOair deal was found by Cheapflights users on 1/23. 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.
Fri 1/309:43 pm
ISP
-
ORD
1 stop19h 57m
Frontier
Sun 2/112:21 pm
ORD
-
ISP
1 stop29h 27m
Frontier
Deal found 1/23$270
This Kiwi.com deal was found by Cheapflights users on 1/22. 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.
Wed 2/47:35 pm
ISP
-
ORD
1 stop15h 08m
Multiple Airlines
Thu 2/54:19 pm
ORD
-
ISP
2 stops27h 28m
Multiple Airlines
Deal found 1/22$280
This Kiwi.com deal was found by Cheapflights users on 1/22. 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 2/67:33 pm
ISP
-
ORD
1 stop22h 02m
Multiple Airlines
Tue 2/1010:07 am
ORD
-
ISP
2 stops24h 03m
Multiple Airlines
Deal found 1/22$288
This Frontier deal was found by Cheapflights users on 1/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/3010:58 am
ISP
-
ORD
1 stop13h 21m
Frontier
Thu 4/24:21 pm
ORD
-
ISP
1 stop6h 34m
Frontier
Deal found 1/23$289
This CheapOair deal was found by Cheapflights users on 1/23. 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 4/203:50 pm
ISP
-
ORD
1 stop9h 08m
Frontier
Sat 4/258:00 am
ORD
-
ISP
1 stop24h 13m
Frontier
Deal found 1/23$290

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 January 24, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$160
(CheapOair)

One-way from

$80
(Frontier)

Popular in

August

Cheapest in

January

Average price

$182
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. 9% potential increase in price ($25 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 January 2026
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 January 24, 2026.
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 2/23

8:23 am-11:15 pm

1 stop15h 52m

Chicago O'Hare Intl

Sat 2/28

8:15 am-7:48 am

1 stop22h 33m

$160

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 2/27

3:34 pm-3:37 pm

1 stop25h 03m

Chicago O'Hare Intl

Sun 3/1

7:35 am-7:38 am

1 stop23h 03m

$230

IslipSt. Louis

ISP - STL

ISPSTL

Islip Long Island

Mon 3/9

2:00 pm-5:50 pm

1 stop4h 50m

Lambert-St Louis

Wed 3/11

6:15 am-11:40 am

1 stop4h 25m

$251

IslipSt. Louis

ISP - STL

ISPSTL

Islip Long Island

Sat 3/7

6:00 pm-11:50 pm

1 stop6h 50m

Lambert-St Louis

Mon 3/9

4:45 pm-11:55 pm

1 stop6h 10m

$259

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Wed 2/4

7:35 pm-9:43 am

1 stop15h 08m

Chicago O'Hare Intl

Thu 2/5

4:19 pm-8:47 pm

2 stops27h 28m

$280

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 2/6

7:33 pm-4:35 pm

1 stop22h 02m

Chicago O'Hare Intl

Tue 2/10

10:07 am-11:10 am

2 stops24h 03m

$288

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 5/7

4:07 pm-2:17 pm

1 stop23h 10m

Chicago O'Hare Intl

Sat 5/9

8:00 am-9:13 am

1 stop24h 13m

$290

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sun 2/8

7:53 pm-4:58 pm

1 stop22h 05m

Chicago O'Hare Intl

Thu 2/12

5:05 am-7:38 am

2 stops25h 33m

$304

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 2/5

7:26 pm-10:46 pm

2 stops28h 20m

Chicago O'Hare Intl

Sun 2/8

10:07 am-6:48 pm

1 stop7h 41m

$395

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 3/6

6:00 am-7:44 pm

1 stop14h 44m

Chicago O'Hare Intl

Sun 3/15

8:05 am-3:49 pm

1 stop6h 44m

$409

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 21 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, December is the cheapest month in which you can book a flight from Islip, New York to Illinois (average of $48). 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 January 24, 2026.
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
4,268 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

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
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

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 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 4h 50m. Frontier provides one of the quickest options available for as low as $251. 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, December is the cheapest month in which you can book a flight from Islip, New York to Illinois (average of $48). 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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Alternative routes for Islip to Illinois

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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 January 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$366Average$932FlexibilityNo cancel feeOn-time63%

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