Flying to your destination on a Sunday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Chicago. Check prices with Cheapflights to find a great deal for your trip.
Users have found that booking a flight from Islip, New York to Chicago at least 56 days early can save you up to 102% on average compared to booking a flight this week. If booking 56 days before your flight isn’t an option for you, users have found flights from Islip, New York to Chicago for as little as $276 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $423 for flights departing within the next 3 days.
February can be a great time to fly to Chicago from Islip, New York with a flight ticket averaging about $262. Cheapflights users have found deals in the month of February for as cheap as $81. The most expensive prices can be found in the month of June.
It’s typically best to fly out from Islip, New York to Chicago in the afternoon. Doing so could potentially save you 68% on the flight price compared to flying at noon, which is usually more expensive.
Fly from
Fly to
Budget
$145 - $205
Route
Depart
Return
Price
Islip Long IslandChicago O'Hare Intl
ISP - ORD
ISPORD
Islip Long Island
Wed 5/29
1 stop9h 19m
Chicago O'Hare Intl
Tue 6/4
1 stop12h 23m
Islip Long IslandChicago O'Hare Intl
ISP - ORD
ISPORD
Islip Long Island
Tue 6/4
1 stop9h 19m
Chicago O'Hare Intl
Wed 6/5
1 stop12h 42m
Islip Long IslandChicago O'Hare Intl
ISP - ORD
ISPORD
Islip Long Island
Wed 8/14
1 stop8h 34m
Chicago O'Hare Intl
Mon 8/19
1 stop13h 30m
Islip Long IslandChicago O'Hare Intl
ISP - ORD
ISPORD
Islip Long Island
Sat 6/1
1 stop9h 09m
Chicago O'Hare Intl
Sun 6/2
1 stop10h 41m
Islip Long IslandChicago O'Hare Intl
ISP - ORD
ISPORD
Islip Long Island
Fri 5/31
1 stop9h 19m
Chicago O'Hare Intl
Mon 6/3
1 stop13h 17m
Islip Long IslandChicago O'Hare Intl
ISP - ORD
ISPORD
Islip Long Island
Sat 5/18
1 stop9h 09m
Chicago O'Hare Intl
Sun 5/19
1 stop13h 17m
Islip Long IslandChicago O'Hare Intl
ISP - ORD
ISPORD
Islip Long Island
Tue 8/20
1 stop8h 34m
Chicago O'Hare Intl
Thu 8/22
1 stop13h 30m
Islip Long IslandChicago O'Hare Intl
ISP - ORD
ISPORD
Islip Long Island
Thu 6/6
1 stop6h 10m
Chicago O'Hare Intl
Thu 6/13
1 stop6h 52m
Islip Long IslandChicago O'Hare Intl
ISP - ORD
ISPORD
Islip Long Island
Tue 5/21
1 stop28h 26m
Chicago O'Hare Intl
Fri 5/24
1 stop13h 17m
Overall
Boarding
Food
Comfort
Crew
Entertainment
Reviews
Had to pay to not have a random seat. Crew did not seem well prepared. Had to take back off right before landing.
Cheapflights makes it easy to find Islip to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Islip.
Yes! Cheapflights helps users easily find flights from Islip to Chicago with no change fees.
Yes, Cheapflights offers price alerts on Islip to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.