Cheap flights from Islip (ISP) to Chicago (CHI) from $55

This is the cheapest one-way flight price, found on 9/23. Prices may vary by date and flight preferences.
ISP — CHI
Oct 1 — Oct 81

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 2023: compare Islip to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

Popular in

July

Cheapest in

September

Round-trip from

$207

One-way from

$76
High demand for flights, 51% potential price rise
Best time to find cheap flights, 47% potential price drop
From Islip Long Island to Chicago (CHI)
One-way flight from Islip Long Island to Chicago (CHI)

ISP - CHI

Price

$207 - $364

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

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

Users have found that booking a flight from Islip to Chicago at least 28 days early can save you up to 32% on average compared to booking a flight this week. If booking 28 days before your flight isn’t an option for you, users have found flights from Islip to Chicago for as little as $277 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 $344 for flights departing within the next 3 days.

What is the cheapest month to fly from Islip to Chicago?

February can be a great time to fly to Chicago from Islip with a flight ticket averaging about $265. Cheapflights users have found deals in the month of February for as cheap as $166. The most expensive prices can be found in the month of June.

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

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Islip to Chicago as you normally would.

Cheap Frontier flights from Islip to Chicago

Cheap Islip to Chicago flights in September & October 2023

The best prices found for ISP to CHI flights for September, October

Islip to Chicago 2023 flight deals

Cheap flights to Chicago from Islip found for this year

Islip to Chicago flights leaving soon

Late deals on return flights to Chicago from Islip, departing today and this week

One-way flights to Chicago from Islip

The cheapest one-way flights from Islip to Chicago

Find flights from Islip to Chicago within your budget

Use the slider to find flights from Islip to Chicago that fit your budget.

Fly from

Any airport

Fly to

Any airport

Budget

$98 - $178

Route

Depart

Return

Price

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Mon 10/16

1 stop14h 34m

Chicago O'Hare Intl

Wed 10/18

1 stop16h 24m

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Thu 11/16

1 stop16h 39m

Chicago O'Hare Intl

Sun 11/19

1 stop10h 52m

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Sat 10/28

1 stop12h 53m

Chicago O'Hare Intl

Tue 10/31

1 stop13h 24m

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Fri 11/17

1 stop17h 10m

Chicago O'Hare Intl

Sun 11/19

1 stop10h 52m

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Sat 11/4

1 stop7h 04m

Chicago O'Hare Intl

Mon 11/6

1 stop12h 18m

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Sat 10/28

1 stop7h 04m

Chicago O'Hare Intl

Tue 10/31

2 stops16h 07m

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Fri 11/3

1 stop22h 43m

Chicago O'Hare Intl

Mon 11/6

1 stop12h 18m

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Tue 10/3

1 stop7h 04m

Chicago O'Hare Intl

Wed 10/4

1 stop9h 17m

Islip Long IslandChicago O'Hare Intl

ISP - ORD

ISPORD

Islip Long Island

Fri 10/20

1 stop14h 07m

Chicago O'Hare Intl

Mon 10/23

1 stop16h 07m

Flights are sorted by cheapest first

Deals found on 9/24

Reviews of airlines servicing Chicago

Southwest
7.6
Good
1,521 reviews

Overall

7.6

Comfort

7.8

Boarding

7.9

Crew

8.4

Entertainment

7.4

Food

6.8

Reviews

1 / 10

Love flying Southwest. The coolest crew, quickest flight, and just smooth altogether.

Southwest
7.6
Good
1,521 reviews
Southwest
7.6
Good
1,521 reviews

Overall

7.6

Comfort

7.8

Boarding

7.9

Crew

8.4

Entertainment

7.4

Food

6.8

Reviews

1 / 10

Love flying Southwest. The coolest crew, quickest flight, and just smooth altogether.

Frontier
5.8
Fair
762 reviews
Southwest
7.6
Good
1,521 reviews

Overall

7.6

Comfort

7.8

Boarding

7.9

Crew

8.4

Entertainment

7.4

Food

6.8

Reviews

1 / 10

Love flying Southwest. The coolest crew, quickest flight, and just smooth altogether.

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 0 airlines. Islip Long Island is conveniently located just 7.2 mi from Islip’s city center.

Can I find flights from Islip to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Islip to Chicago for under $100. The cheapest flight booked recently is on Frontier for just $98, but on average you can expect to pay $184.

Are there last-minute flights available from Islip to Chicago for under $200?

There are currently 5+ open flights from Islip to Chicago within the next 7 days for less than $200.

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

Cheapflights users have booked flights from Islip to Chicago round-trip from $98. This flight start at 74% lower than the current average price 3 months from now.

What does ISP to ORD mean?

ISP and ORD are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. ISP to ORD refers to a flight route from Islip Long Island Airport to Chicago O'Hare Intl Airport. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are some additional IATA codes for airports related to your trip.

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