$133+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — CHI
Nov 17 — Nov 241
Round-trip
1 adult, Economy
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Find cheap flights from Islip to Chicago with Cheapflights
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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
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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 October 18, 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 October 18, 2026.
This Trip.com deal was found by Cheapflights users on 10/15. 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 11/234:40 pm -
1 stop9h 03m
Wed 12/21:19 pm -
1 stop23h 03m
Deal found 10/15![Frontier logo]()
$284
This Frontier deal was found by Cheapflights users on 10/16. 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 12/1811:26 am -
1 stop9h 04m
Sun 12/208:35 pm -
1 stop12h 56m
Deal found 10/16![Frontier logo]()
$328
This Frontier deal was found by Cheapflights users on 10/17. 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
Sat 10/319:51 am -
1 stop6h 40m
Deal found 10/17![Frontier logo]()
$345
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:45 pm -
2 stops5h 35m
Mon 11/94:00 pm -
2 stops6h 35m
Deal found 10/13![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 10/15. 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.
Tue 12/156:30 am -
1 stop9h 25m
Sun 12/208:35 pm -
1 stop11h 10m
Deal found 10/15![Southwest logo]()
$390
This Southwest deal was found by Cheapflights users on 10/16. 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 12/114:25 pm -
1 stop7h 35m
Mon 12/148:50 am -
1 stop6h 25m
Deal found 10/16![Southwest logo]()
$395
This Southwest deal was found by Cheapflights users on 10/16. 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 12/115:35 am -
1 stop4h 05m
Fri 12/112:40 pm -
2 stops7h 55m
Deal found 10/16![Southwest logo]()
$416
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 11/1812:00 pm -
2 stops31h 45m
Wed 12/21:19 pm -
1 stop23h 03m
Deal found 10/16![Multiple Airlines logo]()
$422
This Frontier deal was found by Cheapflights users on 10/15. 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
Sun 10/188:26 am -
1 stop8h 04m
Deal found 10/15![Frontier logo]()
$430
This Priceline deal was found by Cheapflights users on 10/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:00 am -
1 stop8h 42m
Thu 12/35:35 am -
1 stop6h 47m
Deal found 10/16![Multiple Airlines logo]()
$464
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 12/43:02 pm -
2 stops24h 28m
Fri 12/113:30 pm -
1 stop26h 39m
Deal found 10/16![Multiple Airlines logo]()
$467
This Frontier deal was found by Cheapflights users on 10/17. 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 11/214:43 pm -
1 stop9h 00m
Sun 11/225:40 am -
1 stop9h 05m
Deal found 10/17![Frontier logo]()
$471
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 October 18, 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 October 18, 2026.
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:45 pm -
2 stops5h 35m
Mon 11/94:00 pm -
2 stops6h 35m
Deal found 10/13![Southwest logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/2311:55 am -
1 stop9h 30m
Wed 12/28:15 am -
2 stops25h 02m
Deal found 10/15![Multiple Airlines logo]()
$473
This Mytrip deal was found by Cheapflights users on 10/16. 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 10/316:33 pm -
2 stops18h 50m
Wed 11/47:35 pm -
2 stops20h 56m
Deal found 10/16![Frontier logo]()
$556
This Expedia deal was found by Cheapflights users on 10/16. 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.
Sat 10/316:00 am -
1 stop8h 44m
Wed 11/47:00 am -
1 stop13h 37m
Deal found 10/16![JetBlue logo]()
$661
This Southwest deal was found by Cheapflights users on 10/15. 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.
Tue 12/156:30 am -
1 stop9h 25m
Sun 12/208:35 pm -
1 stop11h 10m
Deal found 10/15![Southwest logo]()
$390
This Southwest deal was found by Cheapflights users on 10/16. 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 12/44:05 pm -
1 stop6h 25m
Fri 12/116:10 pm -
1 stop4h 25m
Deal found 10/16![Southwest logo]()
$395
This Southwest deal was found by Cheapflights users on 10/16. 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 12/114:25 pm -
1 stop7h 35m
Mon 12/148:50 am -
1 stop6h 25m
Deal found 10/16![Southwest logo]()
$395
This Southwest deal was found by Cheapflights users on 10/15. 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 11/95:35 am -
1 stop4h 05m
Wed 11/111:15 pm -
2 stops7h 30m
Deal found 10/15![Southwest logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 10/316:33 pm -
1 stop16h 13m
Wed 11/47:35 pm -
2 stops41h 47m
Deal found 10/16![Multiple Airlines logo]()
$537
This Southwest deal was found by Cheapflights users on 10/16. 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.
Tue 11/1712:30 pm -
2 stops6h 55m
Thu 12/38:50 am -
1 stop6h 25m
Deal found 10/16![Southwest logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 12/113:02 pm -
2 stops11h 06m
Mon 12/143:30 pm -
1 stop25h 07m
Deal found 10/16![Multiple Airlines logo]()
$547
This Mytrip deal was found by Cheapflights users on 10/16. 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 11/146:33 pm -
1 stop15h 13m
Sat 11/215:25 am -
2 stops33h 20m
Deal found 10/16![Frontier logo]()
$671
This Expedia deal was found by Cheapflights users on 10/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am -
1 stop8h 44m
Mon 11/27:00 am -
1 stop13h 37m
Deal found 10/14![JetBlue logo]()
$688
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Sun 11/156:33 pm -
1 stop15h 13m
Sat 11/215:26 pm -
2 stops15h 51m
Deal found 10/14![Multiple Airlines logo]()
$592
This Mytrip deal was found by Cheapflights users on 10/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:33 pm -
2 stops15h 41m
Sat 11/212:52 pm -
2 stops23h 53m
Deal found 10/14![Frontier logo]()
$680
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 12/411:55 am -
1 stop11h 54m
Fri 12/113:30 pm -
1 stop26h 39m
Deal found 10/16![Multiple Airlines logo]()
$680
Last-minute flights from Islip to ChicagoDiscover last-minute flight deals from Islip to Chicago. Data last updated October 18, 2026 and is based on user searches.
Discover last-minute flight deals from Islip to Chicago. Data last updated October 18, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 10/15. 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
Sun 10/188:26 am -
1 stop8h 04m
Deal found 10/15![Frontier logo]()
$430
This Frontier deal was found by Cheapflights users on 10/16. 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 10/176:25 pm -
1 stop14h 06m
Sat 10/248:46 am -
1 stop7h 44m
Deal found 10/16![Frontier logo]()
$509
This Frontier deal was found by Cheapflights users on 10/17. 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
Sat 10/319:51 am -
1 stop6h 40m
Deal found 10/17![Frontier logo]()
$345
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:45 pm -
2 stops5h 35m
Mon 11/94:00 pm -
2 stops6h 35m
Deal found 10/13![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 10/15. 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 11/95:40 pm -
1 stop6h 35m
Wed 11/116:00 am -
1 stop4h 45m
Deal found 10/15![Southwest logo]()
$395
This Southwest deal was found by Cheapflights users on 10/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1412:45 pm -
1 stop4h 45m
Sun 11/155:05 am -
1 stop5h 40m
Deal found 10/14![Southwest logo]()
$458
This Priceline deal was found by Cheapflights users on 10/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:00 am -
1 stop8h 42m
Thu 12/35:35 am -
1 stop6h 47m
Deal found 10/16![Multiple Airlines logo]()
$464
This FlightHub deal was found by Cheapflights users on 10/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:00 am -
1 stop18h 36m
Thu 12/37:00 am -
1 stop14h 40m
Deal found 10/16![JetBlue logo]()
$495
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 11/1812:00 pm -
2 stops31h 45m
Wed 12/21:19 pm -
1 stop23h 03m
Deal found 10/16![Multiple Airlines logo]()
$422
This Frontier deal was found by Cheapflights users on 10/17. 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 11/214:43 pm -
1 stop9h 00m
Sun 11/225:40 am -
1 stop9h 05m
Deal found 10/17![Frontier logo]()
$471
This Trip.com deal was found by Cheapflights users on 10/15. 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 11/234:40 pm -
1 stop9h 03m
Wed 12/21:19 pm -
1 stop23h 03m
Deal found 10/15![Frontier logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/2311:55 am -
1 stop9h 30m
Wed 12/28:15 am -
2 stops25h 02m
Deal found 10/15![Multiple Airlines logo]()
$473
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 October 18, 2026.
Search for one-way flight options from Islip to Chicago. Find affordable one-way fares based on user searches. Data last updated October 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/171:38 pm -
3 stops29h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/171:38 pm -
3 stops29h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$144
This Frontier deal was found by Cheapflights users on 10/17. 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 1/1811:59 am -
1 stop8h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$150
This Frontier deal was found by Cheapflights users on 10/17. 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 1/1811:59 am -
1 stop13h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/1412:00 pm -
2 stops12h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/163:02 pm -
2 stops27h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/1112:00 pm -
2 stops22h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/1112:00 pm -
2 stops30h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/163:02 pm -
2 stops28h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$195
This Orbitz deal was found by Cheapflights users on 10/16. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/32:17 pm -
1 stop25h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$196
This Orbitz deal was found by Cheapflights users on 10/16. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/32:17 pm -
1 stop20h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$196
This Southwest deal was found by Cheapflights users on 10/15. 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 11/143:30 pm -
1 stop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Southwest logo]()
$198
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 October 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $284 (Trip.com) |
One-way from | $133 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $829 |
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 October 18, 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
Tue 11/17
1:38 pm-6:30 pm
3 stops29h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$133
IslipChicago
ISP Islip Long Island - ORD Chicago O'Hare Intl
ISPORD
Islip Long Island
Mon 1/18
11:59 am-12:55 am
1 stop13h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$156
IslipChicago
ISP Islip Long Island - ORD Chicago O'Hare Intl
ISPORD
Islip Long Island
Wed 11/11
12:00 pm-9:00 am
2 stops22h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$185
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Wed 11/11
12:00 pm-5:47 pm
2 stops30h 47m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$190
IslipChicago
ISP Islip Long Island - ORD Chicago O'Hare Intl
ISPORD
Islip Long Island
Thu 12/3
10:57 am-6:03 pm
2 stops32h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$195
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Thu 12/3
10:57 am-4:07 pm
2 stops30h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$196
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Sun 11/15
10:57 am-5:47 pm
2 stops31h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$206
IslipChicago
ISP Islip Long Island - ORD Chicago O'Hare Intl
ISPORD
Islip Long Island
Mon 11/16
3:02 pm-3:31 pm
3 stops25h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$217
IslipChicago
ISP Islip Long Island - ORD Chicago O'Hare Intl
ISPORD
Islip Long Island
Sun 11/1
6:33 pm-8:46 am
1 stop15h 13m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$223
Quickest round-trip
IslipChicago
ISP Islip Long Island - MDW Chicago Midway
ISPMDW
Islip Long Island
Sun 11/8
5:35 am-8:40 am
1 stop4h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$239
Showing 1-10 of 37 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 October.
| 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
ISP-MDW
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
ISP-MDW
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 October 18, 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.
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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