What is the cheapest airline that flies from Islip Long Island to Chicago?

Frontier is the most popular carrier operating from Islip Long Island to Chicago

What airlines fly to Chicago?

United Airlines, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from Islip, New York according to our data. United Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Islip Long Island Airport to Chicago?

Prices for flights from Islip Long Island Airport to Chicago refresh daily.

How many operators does momondo search for flights from Islip Long Island Airport to Chicago?

As of December 2025, there is 1 operator available to choose from for flights from Islip Long Island Airport to Chicago.

How old do you have to be to fly from Islip Long Island Airport to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Islip Long Island Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$81 Cheap Flights from Islip to Chicago in 2025/26

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Find the cheapest flights from Islip, New York to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:07 pm - 9:34 pm

ISP

ORD

29h 27m1 stop

8:30 am - 8:40 am

ORD

ISP

23h 10m1 stop

$129Frontier

Sat, Feb 21 - Tue, Feb 24

8:40 pm - 7:17 pm

ISP

ORD

23h 37m1 stop

8:27 pm - 7:45 pm

ORD

ISP

22h 18m1 stop

$163Frontier

Thu, Jan 8 - Sat, Jan 10

7:56 pm - 7:17 pm

ISP

ORD

24h 21m1 stop

10:48 am - 7:51 pm

ORD

ISP

8h 03m1 stop

$220Multiple Airlines

Sat, Jan 10 - Mon, Jan 12

7:56 pm - 5:07 pm

ISP

ORD

22h 11m2 stops

7:21 pm - 11:59 am

ORD

ISP

15h 38m1 stop

$237Multiple Airlines

Sat, Jan 10 - Mon, Jan 12

7:56 pm - 11:35 am

ISP

ORD

16h 39m2 stops

10:48 am - 7:51 pm

ORD

ISP

8h 03m1 stop

$242Multiple Airlines

Sat, Jan 10 - Mon, Jan 12

7:33 pm - 4:35 pm

ISP

ORD

22h 02m1 stop

9:25 am - 8:40 am

ORD

ISP

22h 15m1 stop

$278Frontier

Fri, Jan 23 - Sat, Jan 31

3:34 pm - 10:47 pm

ISP

ORD

8h 13m1 stop

7:35 am - 5:01 pm

ORD

ISP

8h 26m1 stop

$282Frontier

Fri, Feb 27 - Sun, Mar 1

2:31 pm - 9:22 am

ISP

ORD

19h 51m2 stops

1:17 pm - 7:38 am

ORD

ISP

17h 21m1 stop

$291Multiple Airlines

Fri, Feb 13 - Sun, Feb 15

9:43 pm - 4:40 pm

ISP

ORD

19h 57m1 stop

12:21 pm - 6:48 pm

ORD

ISP

29h 27m1 stop

$298Frontier

Fri, Jan 30 - Sun, Feb 1

1:42 pm - 11:38 pm

ISP

ORD

10h 56m1 stop

8:05 am - 4:23 pm

ORD

ISP

7h 18m1 stop

$331Frontier

Fri, Mar 6 - Sun, Mar 8

Frontier flights from Islip, New York to Chicago

Our best Frontier deals on Islip, New York to Chicago flight tickets

Frontier

Feb 21

ISP5:07 pmIslip Long Island

29h 27m

1 stop

ORD9:34 pmChicago O'Hare Intl

Feb 24

ORD8:30 amChicago O'Hare Intl

23h 10m

1 stop

ISP8:40 amIslip Long Island

$129

Find similar

Frontier

Jan 8

ISP8:40 pmIslip Long Island

23h 37m

1 stop

ORD7:17 pmChicago O'Hare Intl

Jan 10

ORD8:27 pmChicago O'Hare Intl

22h 18m

1 stop

ISP7:45 pmIslip Long Island

$163

Find similar

Frontier

Jan 23

ISP7:33 pmIslip Long Island

22h 02m

1 stop

ORD4:35 pmChicago O'Hare Intl

Jan 31

ORD9:25 amChicago O'Hare Intl

22h 15m

1 stop

ISP8:40 amIslip Long Island

$278

Find similar

Southwest flights from Islip, New York to Chicago

Our best Southwest deals on Islip, New York to Chicago flight tickets

Southwest

Mar 5

ISP12:15 pmIslip Long Island

7h 20m

1 stop

ORD6:35 pmChicago O'Hare Intl

Mar 8

ORD1:35 pmChicago O'Hare Intl

8h 20m

1 stop

ISP10:55 pmIslip Long Island

$397

Find similar

Southwest

May 13

ISP9:00 amIslip Long Island

10h 25m

2 stops

ORD6:25 pmChicago O'Hare Intl

May 18

ORD3:05 pmChicago O'Hare Intl

6h 25m

1 stop

ISP10:30 pmIslip Long Island

$402

Find similar

Southwest

May 13

ISP12:30 pmIslip Long Island

10h 25m

2 stops

ORD9:55 pmChicago O'Hare Intl

May 18

ORD7:35 pmChicago O'Hare Intl

15h 20m

2 stops

ISP11:55 amIslip Long Island

$403

Find similar

Fly from

Fly to

Route

Depart

Return

Price

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 2/21

5:07 pm-9:34 pm

1 stop29h 27m

Chicago O'Hare Intl

Tue 2/24

8:30 am-8:40 am

1 stop23h 10m

$129

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Thu 1/8

8:40 pm-7:17 pm

1 stop23h 37m

Chicago O'Hare Intl

Sat 1/10

8:27 pm-7:45 pm

1 stop22h 18m

$163

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 1/10

7:56 pm-7:17 pm

1 stop24h 21m

Chicago O'Hare Intl

Mon 1/12

10:48 am-7:51 pm

1 stop8h 03m

$220

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 1/10

7:56 pm-5:07 pm

2 stops22h 11m

Chicago O'Hare Intl

Mon 1/12

7:21 pm-11:59 am

1 stop15h 38m

$237

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Sat 1/10

7:56 pm-11:35 am

2 stops16h 39m

Chicago O'Hare Intl

Mon 1/12

10:48 am-7:51 pm

1 stop8h 03m

$242

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 1/23

7:33 pm-4:35 pm

1 stop22h 02m

Chicago O'Hare Intl

Sat 1/31

9:25 am-8:40 am

1 stop22h 15m

$278

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 2/27

3:34 pm-10:47 pm

1 stop8h 13m

Chicago O'Hare Intl

Sun 3/1

7:35 am-5:01 pm

1 stop8h 26m

$282

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 2/13

2:31 pm-9:22 am

2 stops19h 51m

Chicago O'Hare Intl

Sun 2/15

1:17 pm-7:38 am

1 stop17h 21m

$291

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 1/30

9:43 pm-4:40 pm

1 stop19h 57m

Chicago O'Hare Intl

Sun 2/1

12:21 pm-6:48 pm

1 stop29h 27m

$298

IslipChicago

ISP - ORD

ISPORD

Islip Long Island

Fri 3/6

1:42 pm-11:38 pm

1 stop10h 56m

Chicago O'Hare Intl

Sun 3/8

8:05 am-4:23 pm

1 stop7h 18m

$331

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Islip, New York to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $291. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Islip, New York to Chicago for around $369.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Islip, New York to Chicago during this time can be as low as $270. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $366.

When to book flights from Islip, New York to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Islip, New York to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Islip, New York to Chicago (ISP to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Islip, New York to Chicago

Fastest flight time	7h 30m
Direct flights	None

The fastest flight from Islip, New York to Chicago takes 7h 30m

There are no direct flights from Islip, New York to Chicago. There are no popular flight routes from Islip, New York to Chicago.

Search flight deals

How far is Islip Long Island to Chicago by plane?
The distance between Islip Long Island and Chicago is about 751.1 mi. Typically, this will take 7h 30m by plane in normal conditions.
When did momondo last update prices for flights from Islip Long Island Airport to Chicago?
Prices for flights from Islip Long Island Airport to Chicago refresh daily.
How many operators does momondo search for flights from Islip Long Island Airport to Chicago?
As of December 2025, there is 1 operator available to choose from for flights from Islip Long Island Airport to Chicago.
How old do you have to be to fly from Islip Long Island Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Islip Long Island Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular airline from Islip, New York to Chicago?
Based on momondo bookings for flights between Islip, New York and Chicago, the leading airline is Southwest, making up 100% of the total bookings.

Best airlines flying from Islip, New York to Chicago

Compare and see reviews for airlines that fly from Islip, New York to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Southwest	PriceFrom $336	Free Cancellation	Rating 8.0 4,257 reviews		Search Southwest flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Islip to Chicago?

It is quick and easy to find Islip to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Islip to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Islip to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Islip to Chicago?

momondo helps you find the best flight between Islip and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Islip to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Islip are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.