Cheap flights from Islip (ISP) to Chicago (CHI)

ISP — CHI
Sep 27 — Oct 41

How to find the cheapest flight from Islip (ISP) to Chicago (CHI)

All the information you need to plan the best ISP to CHI flight in 2022: compare Islip to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

ISP - CHI

Price

$129 - $774

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

Popular inJulyHigh demand for flights, 58% potential price rise
Cheapest inJanuaryBest time to find cheap flights, 61% potential price drop
Round-trip from$129From Islip Long Island to Chicago (CHI)
One-way from$86One-way flight from Islip Long Island to Chicago (CHI)

What is the cheapest day to fly round-trip from Islip, New York to Chicago?

Flying to your destination on a Saturday 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.

How far in advance should I book a flight from Islip, New York to Chicago?

Users have found that booking a flight from Islip, New York to Chicago at least 29 days early can save you up to 25% on average compared to booking a flight this week. If booking 29 days before your flight isn’t an option for you, users have found flights from Islip, New York to Chicago for as little as $255 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 $301 for flights departing within the next 3 days.

What is the cheapest month to fly from Islip, New York to Chicago?

January can be a great time to fly to Chicago from Islip, New York with a flight ticket averaging about $232. Cheapflights users have found deals in the month of January for as cheap as $117. The most expensive prices can be found in the month of June.

When is the cheapest time to fly from Islip, New York to Chicago (ISP - CHI)?

It’s typically best to fly out from Islip, New York to Chicago at noon. Doing so could potentially save you 21% on the flight price compared to flying in the morning, which is usually more expensive.

Cheap flights from Islip to Chicago in September, October 2022

The best prices found for ISP to CHI flights for September, October
Oct 15 - Oct 17
ISP

Islip Long Island

ORD

Chicago O'Hare Intl

1 stop

11h 18m
ORD

Chicago O'Hare Intl

ISP

Islip Long Island

1 stop

16h 27m
$241

Multiple Airlines

Pick Dates

Deal found 9/21/22

Oct 14 - Oct 16
ISP

Islip Long Island

ORD

Chicago O'Hare Intl

1 stop

16h 18m
ORD

Chicago O'Hare Intl

ISP

Islip Long Island

1 stop

15h 28m
$245

Frontier

Pick Dates

Deal found 9/20/22

Oct 15 - Oct 18
ISP

Islip Long Island

ORD

Chicago O'Hare Intl

1 stop

7h 21m
ORD

Chicago O'Hare Intl

ISP

Islip Long Island

1 stop

12h 21m
$276

Multiple Airlines

Pick Dates

Deal found 9/21/22

Islip to Chicago 2022 flight deals

Cheap flights to Chicago from Islip found for this year
Oct 15 - Oct 17
ISP

Islip Long Island

ORD

Chicago O'Hare Intl

1 stop

11h 18m
ORD

Chicago O'Hare Intl

ISP

Islip Long Island

1 stop

16h 27m
$241

Multiple Airlines

Pick Dates

Deal found 9/21/22

Oct 14 - Oct 16
ISP

Islip Long Island

ORD

Chicago O'Hare Intl

1 stop

16h 18m
ORD

Chicago O'Hare Intl

ISP

Islip Long Island

1 stop

15h 28m
$245

Frontier

Pick Dates

Deal found 9/20/22

Oct 15 - Oct 18
ISP

Islip Long Island

ORD

Chicago O'Hare Intl

1 stop

7h 21m
ORD

Chicago O'Hare Intl

ISP

Islip Long Island

1 stop

12h 21m
$276

Multiple Airlines

Pick Dates

Deal found 9/21/22

Cheap Frontier flights from Islip to Chicago

Oct 14 - Oct 16
ISP

Islip Long Island

ORD

Chicago O'Hare Intl

1 stop

16h 18m
ORD

Chicago O'Hare Intl

ISP

Islip Long Island

1 stop

15h 28m
$245

Frontier

Pick Dates

Deal found 9/20/22

Oct 7 - Oct 9
ISP

Islip Long Island

ORD

Chicago O'Hare Intl

1 stop

16h 18m
ORD

Chicago O'Hare Intl

ISP

Islip Long Island

1 stop

15h 18m
$775

Frontier

Pick Dates

Deal found 9/20/22

Mar 10 - Mar 12
ISP

Islip Long Island

ORD

Chicago O'Hare Intl

1 stop

8h 30m
ORD

Chicago O'Hare Intl

ISP

Islip Long Island

1 stop

9h 50m
$1,239

Frontier

Pick Dates

Deal found 9/20/22

Last minute flights from Islip to Chicago

Late deals on return flights to Chicago from Islip, departing today and this week
Sep 30 - Oct 4
ISP

Islip Long Island

ORD

Chicago O'Hare Intl

1 stop

12h 54m
ORD

Chicago O'Hare Intl

ISP

Islip Long Island

2 stops

10h 56m
$368

Multiple Airlines

Pick Dates

Deal found 9/22/22

Sep 30 - Oct 4
ISP

Islip Long Island

ORD

Chicago O'Hare Intl

1 stop

12h 54m
ORD

Chicago O'Hare Intl

ISP

Islip Long Island

1 stop

8h 44m
$380

Multiple Airlines

Pick Dates

Deal found 9/22/22

One-way flights to Chicago from Islip

The cheapest one-way flights from Islip to Chicago
Sep 30
ISP

Islip Long Island

ORD

Chicago O'Hare Intl

1 stop

16h 08m
$86

Frontier

Pick Dates

Deal found 9/22/22

Oct 24
ISP

Islip Long Island

ORD

Chicago O'Hare Intl

1 stop

26h 55m
$115

Frontier

Pick Dates

Deal found 9/19/22

Oct 10
ISP

Islip Long Island

ORD

Chicago O'Hare Intl

1 stop

17h 57m
$124

Multiple Airlines

Pick Dates

Deal found 9/21/22

Related info for your journey

Useful info, stats and facts about Islip to Chicago flights.

What airport do you fly from for flights from Islip to Chicago?

Most people fly from Islip Long Island (ISP) if they book a flight from Islip to Chicago. On average, Long Island has 0 outbound flights to Chicago per day from 2 airlines. Islip Long Island is conveniently located just 7.2 mi from Islip’s city center.

Which airlines flying from Islip Long Island to Chicago have flexible cancellations due to COVID-19?

Some of our airline partners flying from Islip Long Island to Chicago have new flexible policies in place due to COVID-19. American Airlines and Spirit Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like American Airlines with this kind of flexibility.

Can I find flights from Islip, New York to Chicago for under $300 on Cheapflights?

Yes, there are multiple flights from Islip, New York to Chicago for under $300. The cheapest flight booked recently is on Multiple Airlines for just $241, but on average you can expect to pay $1,420.

Are there last-minute flights available from Islip, New York to Chicago for under $400?

There are currently 2+ open flights from Islip, New York to Chicago within the next 7 days for less than $400.

What is the cheapest airline to fly from Islip, New York to Chicago round-trip?

Cheapflights users have booked flights from Islip, New York to Chicago round-trip from $245. Frontier is currently priced 25% below the average price you’ll pay for this route.

What are the cheapest flights from Islip, New York to Chicago?

On average you can expect to pay $251 for a flight from Islip, New York to Chicago. The cheapest flight overall is $212 while the most popular route, (Islip Long Island - Chicago O'Hare Intl) is currently priced at $241.

Alternative routes for Islip to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from Islip to Chicago

The chart below displays the airlines Cheapflights users traveling from Islip to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
American AirlinesCheapest$205Average$407FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights