$119+ Cheap flights from Islip, NY (ISP) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — CHI
Oct 5 — Oct 121
Round-trip
1 adult, Economy
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Find cheap flights from Islip to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Islip to Chicago
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Last-minute
One-way
Cheapest flights from Islip to ChicagoExplore 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 5, 2026.
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 5, 2026.
This Frontier deal was found by Cheapflights users on 9/2. 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 10/246:25 pm -
1 stop14h 06m
Sat 10/319:51 am -
1 stop6h 40m
Deal found 9/2![Frontier logo]()
$236
This Frontier deal was found by Cheapflights users on 9/2. 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 10/106:25 pm -
1 stop14h 06m
Fri 10/168:11 pm -
1 stop20h 19m
Deal found 9/2![Frontier logo]()
$237
This Expedia deal was found by Cheapflights users on 9/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:25 pm -
1 stop14h 06m
Sat 10/248:46 am -
1 stop7h 44m
Deal found 9/1![Frontier logo]()
$257
This Frontier deal was found by Cheapflights users on 8/31. 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 10/166:55 pm -
1 stop13h 56m
Mon 10/198:26 am -
1 stop8h 34m
Deal found 8/31![Frontier logo]()
$260
This Trip.com deal was found by Cheapflights users on 9/3. 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.
Fri 10/166:55 pm -
1 stop13h 56m
Sun 10/186:58 pm -
1 stop22h 02m
Deal found 9/3![Frontier logo]()
$265
This Frontier deal was found by Cheapflights users on 9/2. 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 11/208:01 pm -
1 stop14h 17m
Sun 11/2210:23 am -
1 stop7h 43m
Deal found 9/2![Frontier logo]()
$281
This Frontier deal was found by Cheapflights users on 9/3. 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 10/226:25 pm -
1 stop14h 06m
Sun 10/258:26 am -
1 stop8h 04m
Deal found 9/3![Frontier logo]()
$298
This CheapOair deal was found by Cheapflights users on 9/2. 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 9/245:43 pm -
1 stop17h 37m
Thu 10/13:50 pm -
1 stop24h 08m
Deal found 9/2![Frontier logo]()
$308
This Frontier deal was found by Cheapflights users on 9/4. 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 10/156:25 pm -
1 stop14h 06m
Sun 10/188:26 am -
1 stop8h 04m
Deal found 9/4![Frontier logo]()
$309
This Frontier deal was found by Cheapflights users on 9/4. 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 9/205:43 pm -
1 stop17h 37m
Thu 9/243:50 pm -
1 stop24h 08m
Deal found 9/4![Frontier logo]()
$317
This Frontier deal was found by Cheapflights users on 8/31. 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.
Tue 9/110:57 am -
1 stop13h 11m
Sat 9/57:44 pm -
1 stop13h 09m
Deal found 8/31![Frontier logo]()
$320
Best flights from Islip to ChicagoDiscover carefully curated flight deals from Islip to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 5, 2026.
Discover carefully curated flight deals from Islip to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 5, 2026.
This JetBlue deal was found by Cheapflights users on 8/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 am -
1 stop7h 45m
Fri 9/253:00 pm -
1 stop7h 22m
Deal found 8/31![JetBlue logo]()
$527
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Thu 11/126:33 pm -
1 stop15h 13m
Sat 11/147:20 pm -
2 stops22h 45m
Deal found 9/4![Multiple Airlines logo]()
$539
This Frontier deal was found by Cheapflights users on 9/4. 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 10/106:25 pm -
1 stop14h 06m
Mon 10/128:26 am -
1 stop8h 34m
Deal found 9/4![Frontier logo]()
$649
This JetBlue deal was found by Cheapflights users on 9/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:00 am -
1 stop7h 45m
Fri 10/23:00 pm -
1 stop7h 22m
Deal found 9/2![JetBlue logo]()
$527
This JetBlue deal was found by Cheapflights users on 8/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:00 am -
1 stop7h 45m
Fri 10/23:00 pm -
1 stop7h 22m
Deal found 8/31![JetBlue logo]()
$579
This KAYAK deal was found by Cheapflights users on 9/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:00 am -
1 stop17h 08m
Fri 9/256:00 am -
1 stop16h 22m
Deal found 9/2![JetBlue logo]()
$586
This JetBlue deal was found by Cheapflights users on 9/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:00 am -
1 stop7h 45m
Sat 9/263:00 pm -
1 stop7h 22m
Deal found 9/2![JetBlue logo]()
$611
This JetBlue deal was found by Cheapflights users on 9/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 am -
1 stop7h 45m
Wed 9/233:00 pm -
1 stop7h 22m
Deal found 9/1![JetBlue logo]()
$675
This JetBlue deal was found by Cheapflights users on 8/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/275:55 am -
1 stop8h 44m
Mon 3/17:00 am -
1 stop8h 55m
Deal found 8/31![JetBlue logo]()
$687
This JetBlue deal was found by Cheapflights users on 9/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:00 am -
1 stop7h 45m
Wed 9/303:00 pm -
1 stop7h 22m
Deal found 9/2![JetBlue logo]()
$715
This JetBlue deal was found by Cheapflights users on 8/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/245:55 am -
1 stop8h 44m
Mon 3/17:00 am -
1 stop8h 55m
Deal found 8/31![JetBlue logo]()
$743
Last-minute flights from Islip to ChicagoDiscover last-minute flight deals from Islip to Chicago. Data last updated September 5, 2026 and is based on user searches.
Discover last-minute flight deals from Islip to Chicago. Data last updated September 5, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 8/31. 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 9/510:57 am -
1 stop13h 11m
Mon 9/79:10 pm -
1 stop11h 43m
Deal found 8/31![Frontier logo]()
$330
This Frontier deal was found by Cheapflights users on 9/4. 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 9/205:43 pm -
1 stop17h 37m
Thu 9/243:50 pm -
1 stop24h 08m
Deal found 9/4![Frontier logo]()
$317
This CheapOair deal was found by Cheapflights users on 9/2. 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 9/245:43 pm -
1 stop17h 37m
Thu 10/13:50 pm -
1 stop24h 08m
Deal found 9/2![Frontier logo]()
$308
This Frontier deal was found by Cheapflights users on 9/2. 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 10/106:25 pm -
1 stop14h 06m
Fri 10/168:11 pm -
1 stop20h 19m
Deal found 9/2![Frontier logo]()
$237
This Frontier deal was found by Cheapflights users on 9/4. 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 10/156:25 pm -
1 stop14h 06m
Sun 10/188:26 am -
1 stop8h 04m
Deal found 9/4![Frontier logo]()
$309
This Frontier deal was found by Cheapflights users on 8/31. 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 10/166:55 pm -
1 stop13h 56m
Mon 10/198:26 am -
1 stop8h 34m
Deal found 8/31![Frontier logo]()
$260
This Trip.com deal was found by Cheapflights users on 9/3. 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.
Fri 10/166:55 pm -
1 stop13h 56m
Sun 10/186:58 pm -
1 stop22h 02m
Deal found 9/3![Frontier logo]()
$265
This Expedia deal was found by Cheapflights users on 9/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:25 pm -
1 stop14h 06m
Sat 10/248:46 am -
1 stop7h 44m
Deal found 9/1![Frontier logo]()
$257
This Frontier deal was found by Cheapflights users on 9/3. 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 10/226:25 pm -
1 stop14h 06m
Sun 10/258:26 am -
1 stop8h 04m
Deal found 9/3![Frontier logo]()
$298
This Frontier deal was found by Cheapflights users on 9/2. 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 10/246:25 pm -
1 stop14h 06m
Sat 10/319:51 am -
1 stop6h 40m
Deal found 9/2![Frontier logo]()
$236
One-way flights from Islip to ChicagoSearch for one-way flight options from Islip to Chicago. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
Search for one-way flight options from Islip to Chicago. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
This CheapOair deal was found by Cheapflights users on 8/31. 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 9/235:43 pm -
1 stop17h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![Frontier logo]()
$119
This Frontier deal was found by Cheapflights users on 9/1. 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 10/106:25 pm -
1 stop14h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Frontier logo]()
$124
This Frontier deal was found by Cheapflights users on 8/31. 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 10/196:55 pm -
1 stop13h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![Frontier logo]()
$135
This Frontier deal was found by Cheapflights users on 9/2. 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 10/256:25 pm -
1 stop14h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$137
This CheapOair deal was found by Cheapflights users on 9/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:43 pm -
1 stop17h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Frontier logo]()
$138
This CheapOair deal was found by Cheapflights users on 9/3. 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 11/136:54 pm -
1 stop14h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$140
This Frontier deal was found by Cheapflights users on 9/1. 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.
Fri 10/96:55 pm -
1 stop13h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Frontier logo]()
$156
This CheapOair deal was found by Cheapflights users on 9/2. 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 9/245:43 pm -
1 stop17h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$168
This CheapOair deal was found by Cheapflights users on 9/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:43 pm -
1 stop17h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Frontier logo]()
$178
This Trip.com deal was found by Cheapflights users on 9/4. 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.
Mon 10/266:55 pm -
1 stop23h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$179
This Frontier deal was found by Cheapflights users on 9/2. 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.
Tue 11/248:01 pm -
1 stop14h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$185
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 September 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $236 (Frontier) |
One-way from | $119 (CheapOair) |
Popular in | March |
Cheapest in | August |
Average price | $334 |
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 7,457,451 searches. Data last updated September 5, 2026.
Use the filters below to find and compare flights from Islip to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
IslipChicago
ISP Islip Long Island - ORD Chicago O'Hare Intl
ISPORD
Islip Long Island
Sat 10/17
6:25 pm-7:31 am
1 stop14h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$124
IslipChicago
ISP Islip Long Island - ORD Chicago O'Hare Intl
ISPORD
Islip Long Island
Sun 10/18
6:25 pm-7:31 am
1 stop14h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$137
IslipChicago
ISP Islip Long Island - ORD Chicago O'Hare Intl
ISPORD
Islip Long Island
Sun 10/11
6:25 pm-7:31 am
1 stop14h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$137
IslipChicago
ISP Islip Long Island - ORD Chicago O'Hare Intl
ISPORD
Islip Long Island
Fri 10/16
6:55 pm-7:51 am
1 stop13h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$137
IslipChicago
ISP Islip Long Island - ORD Chicago O'Hare Intl
ISPORD
Islip Long Island
Mon 10/26
6:55 pm-5:03 pm
1 stop23h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
Quickest round-trip
IslipChicago
ISP Islip Long Island - ORD Chicago O'Hare Intl
ISPORD
Islip Long Island
Sat 9/26
7:00 am-1:45 pm
1 stop7h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$274
IslipChicago
ISP Islip Long Island - ORD Chicago O'Hare Intl
ISPORD
Islip Long Island
Wed 10/21
6:00 am-1:50 pm
1 stop8h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$274
IslipChicago
ISP Islip Long Island - ORD Chicago O'Hare Intl
ISPORD
Islip Long Island
Thu 9/24
7:00 am-1:45 pm
1 stop7h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$306
IslipChicago
ISP Islip Long Island - ORD Chicago O'Hare Intl
ISPORD
Islip Long Island
Sat 10/31
6:00 am-1:44 pm
1 stop8h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$362
IslipChicago
ISP Islip Long Island - ORD Chicago O'Hare Intl
ISPORD
Islip Long Island
Mon 9/21
7:00 am-1:45 pm
1 stop7h 45m
Chicago O'Hare Intl
Fri 9/25
3:00 pm-11:22 pm
1 stop7h 22m
$527
Showing 1-10 of 20 resultsSorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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.
ISP-CHI
ISP-ORD
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
ISP-CHI
ISP-ORD
No data available for this route at this time. Please check back soon.
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 5, 2026.
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.
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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